Brooks Cole Laboratory Series for Chemistry

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Brooks/Cole Laboratory Series for Chemistry http://chemistry.brookscole.com

Chemical Education Resources http://www.CERLabs.com

ISBN: 0-534-42025-7

http://chemistry.brookscole.com http://www.CERLabs.com

ABOUT THIS CATALOG By devoting our new catalog specifically to chemistry lab texts, we hope to make it easier for you to find the resources you need for your chemistry lab course. No matter how you teach your chemistry course, you’ll find lab resources in this catalog designed to complement your teaching style and develop your students’ lab skills, topic by topic—flexibly, economically, and with lab resources of the highest quality. For the first time, we’ve combined the economy and flexibility of the modular lab program from Chemical Education Resources (CER) with the high quality content from the market-leading lab manuals in the Brooks/Cole Laboratory Series for Chemistry. You can now select from more than 300 CER experiments, draw material from the Brooks/Cole Lab Series, and even add your own lab materials to custom-build a total lab solution that exactly meets your teaching needs. Brooks/Cole’s Laboratory Series for Chemistry, featured on pages 3–35, includes some of the best selling lab manuals for your course, whether you’re teaching Introductory/Prep, Liberal Arts, Allied Health/Health Sciences, General, Organic, or Biochemistry. Our Lab Series not only includes manuals from some of the most respected lab manual authors in the business, like Slowinski and Pavia, but also reflects new trends in teaching, with manuals featuring Guided Inquiry, Green Chemistry, and integration of new lab tools such as MeasureNet. Because we want to offer you the greatest possible flexibility in assembling resources for your labs, any of these lab manuals can be customized to meet your particular course needs. As part of our commitment to building an extensive and cohesive collection of lab materials for you to draw from, our new lab manuals feature a new, more uniform design to give your custom manuals a consistent look no matter which materials you choose to include. To help you build your custom manual, we’ve also provided suggestions for the individual CER modules most appropriate for each course, which can be used on their own or in combination with material from our Lab Series. Learn more about building a customized, modular lab manual on pages 36–38, where we provide you with detailed information about CER’s modular lab program for chemistry. We’ll explain how the format and pedagogy of CER labs have been proven to help students master lab skills, give you an overview of our outstanding online instructor resources, and provide you with abstracts for more than 300 of our lab modules. Most importantly, we’ll show you how to build your custom lab manual on our website in minutes. And look to pages 76–79 for information on Brooks/Cole chemistry textbooks, lab notebooks, and chemistry handbooks—including special offers for ordering a lab notebook or chemistry handbook together with Brooks/Cole and CER labs! Welcome to Brooks/Cole and CER…the total solution for your chemistry lab. http://chemistry.brookscole.com http://www.CERLabs.com

TABLE OF CONTENTS

Brooks/Cole Laboratory Series

Chemical Education Resources

Introductory/Preparatory Chemistry ........................... 3

A Commitment to Service and Community................ 36

Proven Features & Support ....................................... 37

Introduction to Chemical Principles: A Laboratory Approach, 6e ................................................................. 3 Course Suggestions ............................................ 4

Building Your Own Customized Lab Manual.............. 38

Liberal Arts Chemistry................................................. 6

Experiment Descriptions: First Year Labs .................. 39

Lab Manual for the World of Chemistry, 2e .................... 6

Allied Health/Health Sciences Chemistry ..................... 6

Safety Scale Laboratory Experiments for Chemistry For Today: General, Organic, and Biochemistry, 5e............... 6 Laboratory Experiments for General, Organic, and Biochemistry, 5e ............................................................ 7 Course Suggestions ............................................ 9

General Chemistry..................................................... 11

Experiments in General Chemistry Featuring MeasureNet .................................................. Lab Experiments for General Chemistry, 5e................... Chemical Principles in the Laboratory, 8e ..................... Laboratory Inquiry in Chemistry, 2e.............................. Standard Microscale Experiments in General Chemistry, 5e .................................................. Experiments in General Chemistry, 4e ........................... Laboratory Handbook for General Chemistry, 2e .......... Course Suggestions ..........................................

11 12 13 14 15 17 18 19

Organic Chemistry .................................................... 23

Introduction to Organic Laboratory Techniques: A Small Scale Approach, 2e .......................................... Theory and Practice in the Organic Laboratory with Microscale and Standard Scale Experiments, 5e ............ Green Organic Chemistry: Strategies, Tools, and Laboratory Experiments ............................................... Experimental Organic Chemistry: A Miniscale and Microscale Approach, 3e .............................................. Microscale and Macroscale Techniques in the Organic Laboratory...................................................... Organic Chemistry Laboratory: Standard and Microscale Experiments, 3e .......................................... Organic Laboratory Techniques, 3e .............................. Introduction to Spectroscopy, 3e.................................. Introduction to Organic Laboratory Techniques: A Microscale Approach, 3e........................................... Course Suggestions ..........................................

Analysis............................................................ Electrochemistry ............................................... Equilibrium ...................................................... Kinetics ............................................................ Miscellaneous................................................... Properties ........................................................ Reactions ......................................................... Stoichiometry ................................................... Structure .......................................................... Synthesis .......................................................... Techniques ....................................................... Thermodynamics ..............................................

39 46 47 50 50 52 56 60 63 64 65 67

Experiment Descriptions: Organic Chemistry Labs .... 69 Analysis............................................................ Kinetics ............................................................ Miscellaneous................................................... Reactions ......................................................... Synthesis .......................................................... Techniques .......................................................

69 69 70 70 71 74

23

Lab Handbook & Lab Notebooks

25

Lab Handbook & Lab Notebooks .............................. 76

27

Bundling Options

28

Bundling Options ...................................................... 77

29

Review Copy Request Form

29 30 31

Textbooks ................................................................. 80

32 34

Biochemistry ............................................................. 35

2

Experiments in Biochemistry: A Hands-on Approach, 2e ............................................................... 35

Brooks/Cole Laboratory Series & Chemical Education Resources

BROOKS/COLE LABORATORY SERIES Introductory/Preparatory Chemistry

NEW!

Introduction to Chemical Principles: A Laboratory Approach, 6e Susan A. Weiner — West Valley College 432 pages | Paperbound | 8-1/2 x 11 | ©2005 | 0-534-40777-3

The sixth edition of this superb lab manual offers 34 class-tested experiments, suitable for introductory and preparatory chemistry courses and texts, including Introductory Chemistry: An Active Learning Approach, Second Edition by Cracolice and Peters. Experiments in this lab manual teach students to collect and analyze experimental data and provide them with a strong foundation for further course work in general chemistry. This edition offers instructors a wide variety of experiments to customize their laboratory program, including many microscale experiments. All experiments can be completed in a three-hour laboratory period. As in the Fifth Edition, there are “Work Pages” for each experiment as well as “Report Sheets,” for students to take notes, record experimental data and results, which facilitate the instructor in grading the experiments.

NEW TO THIS EDITION The new edition features eleven worksheets covering the major topics of introductory chemistry. The worksheets can be used in addition to experiments or as supplementary homework, with complete solutions available in the Instructor’s Manual. The Sixth Edition also features two new experiments: “Experiment 14: Separation of Cations,” which requires a qualitative analysis of five cations, and “Experiment 24: Determination of a Chemical Equation.” The latter experiment focuses on quantitative analysis, emphasizing ‘hands on’ chemistry and teaching the student to derive a chemical equation from the experimental data. Several experiments have been revised to provide clearer direction and more detail in the “Procedure” section.

KEY FEATURES Duplicate “Work Pages” and “Report Sheets” for each experiment offer a convenient and efficient way for students to record their data as they work and yield clean, easy to grade reports.

http://chemistry.brookscole.com

“Advanced Study Assignments,” to be completed before performing the experiments, require students to read the experiment before executing the lab, thus enabling them to complete the experiment in a safe and timely fashion. “Sample Calculations” are presented to acquaint the student with the type of calculations they will be required to perform for the experiment. The lab manual features a variety of experiments for inorganic and organic chemistry so that it may accompany many different chemistry textbooks from introductory inorganic chemistry to allied health chemistry. Laboratory and safety procedures are addressed in each experiment, as well as disposal methods, performance goals, chemical overview with key terms, and expanded coverage of experiment procedures. Microscale experiments are denoted in the table of contents by an “(m)” following the title of the experiment.

TA B L E O F C O N T E N T S SAFETY IN THE LABORATORY. LABORATORY PROCEDURES. EXPERIMENTS: 1. Properties and Changes of Matter (m). 2. Calibration of a Thermometer. 3. Separation of Cations by Paper Chromatography (m). 4. Densities of Liquids and Solids. 5. Simplest Formula of a Compound (m). 6. Hydrates (m). 7. Percentage of Oxygen in Potassium Chlorate. 8. Calorimetry. 9. Chemical Names and Formulas: A Study Assignment. 10. Chemical Equations: A Study Assignment. 11. Mole Ratio for a Chemical Reaction (m). 12. Types of Chemical Reactions (m). 13. Qualitative Analysis of Some Common Ions (m). 14. Separation of Cations (m). 15. Molar Volume of Gas. 16. Molar Mass of a Gas (m). 17. Molar Mass of a Volatile Liquid. 18. Molar Mass of Determination by FreezingPoint Depression. 19. The Conductivity of Solutions: A Demonstration. 20. Net Ionic Equations: A Study Assignment. 21. The Chemistry of Some Household Products (m). 22. Titration of Acids and Bases--An Introduction. 23. Titration of Acids and Bases--II. 24. Determination of a Chemical Equation. 25. A Study of Reaction Rates. 26. Chemical Equilibrium (m). 27. Measurement of pH with Indicators. 28. Introduction to Oxidation-Reduction Reactions (m). 29. Hydrocarbons and Alcohols. 30. Aldehydes, Ketones, and Carboxylic Acids. 31. Preparation of Aspirin. 32. Preparation and Properties of a Soap. 33. Carbohydrates. 34. Amino Acids and Proteins. WORKSHEETS: 1. Dimensional Analysis. 2. Avogrado’s Number-Moles. 3. Formula Writing. 4. Equation Balancing-Types of Reactions. 5. Stoichiometry. 6. Atomic Structure. 7. Gases. 8. Solutions. 9. Oxidation-Reduction. 10. Acids and Bases. Appendix.

BROOKS/COLE LABORATORY SERIES

INTRODUCTORY/PREPARATORY CHEMISTRY

ANCILLARIES Online Instructor’s Manual

http://chemistry.brookcole.com

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BROOKS/COLE LABORATORY SERIES Introductory/Preparatory Chemistry: CER Course Suggestions

C O U R S E R E C O M M E N DAT I O N S I N T R O D U C T O RY / P R E PA R AT O RY C H E M I S T RY TECHNIQUES TECH TECH TECH TECH TECH TECH

380: Safety Practices in the Chemistry Laboratory 381: The Gas Burner and Glass Working 485: Measuring Mass 511: Laboratory Techniques: Measuring the Volume of Liquids 600: Practicing Safety in the Chemistry Laboratory 601: Introducing Mass and Volume Measurements

PROP PROP PROP PROP PROP PROP PROP PROP PROP

CER COURSE SUGGESTIONS

MISCELLANEOUS MISC 371: Introducing Graphic Techniques MISC 459: Naming Inorganic Compounds MISC 476: Interpreting and Balancing Chemical Equations MISC 477: Writing and Balancing Chemical Equations MISC 486: Dimensional Analysis MISC 490: Using Exponential Notation and Significant Figures MISC 614: Writing, Interpreting, and Balancing Chemical Equations MISC 629: Naming Inorganic Chemical Substances MISC 636: Solving Stoichiometric Problems MISC 639: Introducing the IUPAC Nomenclature of Organic Chemical Compounds MISC 873: Introduction to Computer-Based Graphical Analysis LabWorks (Windows) MISC 874: Introduction to Computer-Based Graphical Analysis TI83 Graphing Calculator MISC 875: Introduction to Computer-Based Graphical Analysis Vernier Graphical Analysis for Windows MISC 876: Introduction to Computer-Based Graphical Analysis Microsoft Excel 5 MISC 877: Introduction to Computer-Based Graphical Analysis Microsoft Excel 97

PROPERTIES PROP 374: Separating a Binary Mixture PROP 383: Density of Liquids and Solids PROP 384: Charles’s Law PROP 385: Diffusion of Gases PROP 391: Solutions PROP 393: Studying Density Using Salad Oil and Vinegar PROP 407: Determining the Molar Volume of Carbon Dioxide PROP 412: Diffusion of Gases and Graham’s Law PROP 454: Osmosis and Dialysis PROP 460: Separating and Isolating the Components of a Binary System PROP 461: Separating and Isolating the Components of a Ternary System PROP 474: Investigating Density, Miscibility, and Solubility

495: Classifying Matter by Properties 513: Separating and Isolating the Major Components of Milk 602: Determining Density 603: Resolving a Two-Component Mixture 608: Calculating the Molar Volume of Carbon Dioxide 615: Studying Some Aspects of Solubility 621: Isolating the Components of a Three-Component Mixture 627: Observing Some Physical and Chemical Changes in Matter 632: Studying Charles’ Law

REACTIONS REAC 389: Single Replacement Reactions and Relative Reactivity REAC 390: Double Replacement Reactions REAC 399: Detecting Signs of Chemical Change REAC 405: Identifying Six Solutions by Their Interaction REAC 413: Preparing and Studying Oxygen and Some of Its Compounds REAC 414: Determining the Comparative Reactivities of Several Metals REAC 456: Studying Oxidation-Reduction Reactions REAC 502: Establishing the Relative Reactivity of Halogens and Halide Ions REAC 604: Observing Signs of Chemical Reaction REAC 610: Observing Single Replacement Reactions REAC 611: Observing Some Double Replacement Reactions REAC 613: Classifying Some Chemical Reactions REAC 626: Observing Some Oxidation-Reduction Reactions REAC 634: Identifying Solutions of Ionic Compounds REAC 635: Discovering Some Periodic Properties of Elements

SYNTHESIS SYNT SYNT SYNT SYNT SYNT SYNT

341: Synthesis of Strontium Iodate Monohydrate 347: Preparation of Strontium Iodate Monohydrate 439: Synthesizing Aspirin 451: Synthesizing Alum 612: Preparing Alum 628: Preparing Aspirin continued on next page...

See pages 39–75 for a complete description for CER labs or go online to http://www.CERLabs.com.

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BROOKS/COLE LABORATORY SERIES Introductory/Preparatory Chemistry: CER Course Suggestions

I N T R O D U C T O RY / P R E PA R AT O RY C H E M I S T RY STOICHIOMETRY STOI 386: Determining the Empirical Formula of Copper Chloride STOI 388: The Empirical Formula of an Oxide STOI 420: Precipitating Lead Chromate on a Small Scale STOI 606: Determining the Empirical Formula of Magnesium Oxide STOI 607: Reacting Baking Soda with Vinegar to Find Percent Acetic Acid STOI 633: Determining the Empirical Formula of a Compound Containing Copper and Chlorine STOI 637: Determining the Stoichiometry of a Double Displacement Reaction

STRUCTURE STRC 435: Chemical Models: Ball-and-Stick Models of Organic Compounds STRC 631: Visualizing Chemical Structures Using Lewis Models

KINETICS KINE 505: Studying the Rate of Reaction

EQUILIBRIUM EQUL 397: pH, Acids, and Bases EQUL 411: Estimating the pH of Household Products Using Red Cabbage Extract as an Indicator EQUL 465: Using Acid-Base Indicators to Visually Estimate the pH of Solutions EQUL 616: Introducing Chemical Equilibrium EQUL 617: Estimating the pH of Some Solutions Using Visual Indicators

THERMODYNAMICS

ELECTROCHEMISTRY ELEC 419: Studying Electrochemistry and Establishing the Relative Reactivity of a Series of Metals ELEC 450: Studying Electrochemical Half-Cells and Half-Reactions

ANALYSIS ANAL 238: Determining Ascorbic Acid in Vitamin C Tablets ANAL 394: Determining the Molar Concentration of a Sodium Hydroxide Solution ANAL 395: Titrating Vinegar ANAL 396: Introducing the Qualitative Analysis of a Group of Cations ANAL 415: Introducing Volumetric Techniques by Analyzing Bleaching Solution ANAL 426: Standardizing a Sodium Hydroxide Solution with a Standard Hydrochloric Acid Solution ANAL 427: Quantitatively Determining the Acid Content of Fruit Juices ANAL 464: Comparing the Resistance of Buffered and Unbuffered Solutions to pH Change ANAL 466: Standardizing a Sodium Hydroxide Solution and Using it to Analyze Vinegar ANAL 478: Evaluating Commercial Antacids ANAL 492: Separating and Identifying Food Dyes by Paper Chromatography ANAL 605: Determining the Percent Water in an Unknown Hydrate ANAL 618: Standardizing a Sodium Hydroxide Solution ANAL 619: Titrating the Acetic Acid in Vinegar ANAL 620: Separating and Identifying FD&C Dyes Using Paper Chromatography ANAL 622: Analyzing the Vitamin C in Fruit Juices ANAL 624: Identifying Cations in a Solution ANAL 625: Estimating the Acid Content of Fruit Juices ANAL 638: Determining the Acid-Neutralizing Capacity of Common Antacids


M O R E C O U R S E R E C O M M E N DAT I O N S

THER 346: Enthalpy of Neutralization THER 368: Heat of Neutralization THER 428: Estimating the Calorie Content of Nuts THER 609: Estimating a Heat of Neutralization THER 623: Estimating the Calorie Content of Peanuts THER 630: Estimating the Heat of Decomposition of Hydrogen Peroxide THER 883: Heat of Neutralization Texas Instruments CBL System THER 885: Heat of Neutralization LabWorks Interface (Windows 95) THER 887: Heat of Neutralization Vernier Logger Pro for Windows


View or print review copies and access instructor resources at http://www.CERLabs.com

5

BROOKS/COLE LABORATORY SERIES Liberal Arts Chemistry — Allied Health/Health Sciences Chemistry LIBERAL ARTS CHEMISTRY

ALLIED HEALTH/HEALTH SCIENCES CHEMISTRY

NEW!


Lab Manual for the World Of Chemistry, 2e

6

JOHN R. BLACKBURN — Georgetown College; MELVIN D. JOESTEN — Vanderbilt University; PAUL B. LANGFORD — David Lipscomb College; and JOHN C. CRAIG — Consultant, West Point, Mississippi

Safety Scale Laboratory Experiments for Chemistry For Today: General, Organic, and Biochemistry, 5e

332 pages | Paperbound | ©1996 | 0-03-007442-8

Spencer L. Seager — Weber State University; and Michael R. Slabaugh — Weber State University

Intended for the liberal arts chemistry course with a lab, this manual provides a wide range of experiments

591 pages | Paperbound | 8-1/2 x 11 | ©2005 | 0-534-39970-3

ANCILLARIES Instructor’s Manual Student Lab Research Notebook Long Version, Top-bound Short Version, Top-bound

0-03-004497-9 0-03-027288-2 0-03-027289-0

The Fifth Edition of this accurate and well-tested lab manual contains 15 general chemistry and 20 organic/biochemistry safety-scale laboratory experiments. The experiments are designed to use small quantities of chemicals and emphasize safety and proper disposal of materials. “Safety-scale” is the authors’ own term for describing the amount of chemicals each lab experiment requires—less than macroscale quantities, which are expensive and hazardous, and more than microscale quantities, which are difficult to work with and require special equipment. This lab manual provides a unique blend of laboratory skills and exercises that effectively illustrate concepts from the main text, Chemistry for Today: General, Organic, and Biochemistry, Fifth Edition.

NEW TO THIS EDITION The Fifth Edition features a new Experiment 34, “Extraction of DNA from Wheat Germ.” In this experiment, two conditions--heat and a proteolytic enzyme from commercial meat tenderizer--are used to denature cellular proteins that interfere with the extraction. In addition, the effect of detergent on cell membranes is demonstrated. The Fifth Edition also includes new Experiment 35, “Detection of Minerals in Breakfast Cereals.” The students work in teams to prepare cereal extracts from samples that have been ashed by heating to a high temperature. The extracts are then tested for the presence of calcium, copper, iron, zinc, sodium and potassium. The experiment is designed so each student gets the opportunity to test extracts from at least five cereals and compare the results.


BROOKS/COLE LABORATORY SERIES Allied Health/Health Sciences Chemistry

For maximum flexibility and convenience, this paperbound manual is three-hole punched and features perforated pages—allowing students to easily hand in lab reports and answers to pre- and post-lab questions and exercises upon instructor request.

TA B L E O F C O N T E N T S 1. Measurements and Significant Figures. 2. The Use of Chemical Balances. 3. The Use of Volumetric Ware and the Determination of Density. 4. Physical and Chemical Changes. 5. Separations and Analysis. 6. Classification of Chemical Reactions. 7. Analysis Using Decomposition Reactions. 8. Gas Laws. 9. Solution Formation and Characteristics. 10. Colligative Properties of Solutions. 11. Reaction Rates and Equilibrium. 12. Acids, Bases, Salts, and Buffers. 13. Analysis of Vinegar. 14. Determination of Ka for Weak Acids. 15. The Acidic Hydrogens of Acids. 16. The Use of Melting Points in the Identification of Organic Compounds. 17. Isolation and Purification of an Organic Compound. 18. Hydrocarbons. 19. Reactions of Alcohols and Phenols. 20. Reactions of Aldehydes and Ketones. 21. Reactions of Carboxylic Acids, Amines, and Amides. 22. The Synthesis of Aspirin and Other Esters. 23. Identifying Functional Groups in Unknowns. 24. Synthetic Polymers. 25. Dyes, Inks, and Food Colorings. 26. A Study of Carbohydrates. 27. Preparation of Soap by Lipid Saponification. 28. Isolation of Natural Products: Trimyristin and Cholesterol. 29. Amino Acids and Proteins. 30. Enzymes: Nature’s Catalysts. 31. Factors That Influence Enzyme Activity. 32. Vitamin C Content of Foods, Part I. 33. Vitamin C Content of Foods, Part II: Samples from Home. 34. Extraction of DNA from Wheat Germ. 35. Detection of Minerals in Breakfast Cereals. Appendix A: Graphs and Graphing. Appendix B: Equipment, Chemicals, Reagents, and Supplies. Appendix C: Table of Atomic Weights and Numbers.



Laboratory Experiments For General, Organic, And Biochemistry, 5e Frederick A. Bettelheim and Joseph M. Landesberg — both of Adelphi University 573 pages | Paperbound | 8-1/2 x 11 | ©2004 | 0-534-40192-9

The 52 experiments in this well-conceived manual illustrate important concepts and principles in general, organic, and biochemistry. As in previous editions, three basic goals guided the development of all the experiments. The experiments illustrate the concepts learned in the classroom. The experiments are clearly and concisely written so that students will easily understand the task at hand, will work with minimal supervision, and will be able to perform the experiments in a 2 1/2-hour laboratory period. Finally, the experiments are not only simple demonstrations, but also promote a sense of discovery.

NEW TO THIS EDITION This edition includes many revised experiments and three new experiments: Fermentation of a Carbohydrate: Ethanol from Sucrose, Neurotransmission: An Example of Specificity, and Isolation and Identification of DNA from Onion. As a result of the authors’ continuing first-hand laboratory observations, a number of experiments feature improved procedures. Safety issues and waste disposal are emphasized throughout this edition. Use of hazardous chemicals is minimized where possible and experiments are designed to work either on a small scale or on a semi-micro scale. Most Pre-Lab and Post-Lab Questions have been changed or modified.

KEY FEATURES The procedures for all experiments are based on the authors’ first-hand lab experience in their laboratories at Adelphi University. The Table of Contents is organized so that the first 23 experiments illustrate the principles of general chemistry, the next 12 those of organic chemistry, and remaining 17 those of biochemistry. Each experiment starts out with a Background section that contains information beyond the textbook material. All the relevant principles and their applications are reviewed in this Background section.



KEY FEATURES

7



Allied Health/Health Sciences Chemistry

8

The Procedure section provides a step-by-step description of the experiments. Clarity of writing in this section is of the utmost importance for successful execution of the experiments. Caution! signs alert students when dealing with dangerous chemicals, such as strong acids or bases. Pre-Lab Questions are provided to familiarize students with the concepts and procedures before they start the experiments. Report Sheets not only ask for the recording of raw data, but also requests some calculations to yield secondary data. The Post-Lab Questions are designed so that students should be able to reflect upon the results, interpret them, and relate their significance. Appendix 3 provides Stockroom Personnel with detailed instructions on preparation of solutions and other chemicals for each experiment. Detailed instructions as to how much material is needed for a class of 25 students is also provided.

Neurotransmission: An Example of Enzyme Specificity. 46. Isolation and Identification of DNA from Onion. 47. Viscosity and Secondary Structure of DNA. 48. Kinetics of Urease Catalyzed Decomposition of Urea. 49. Isocitrate Dehydrogenase: An Enzyme of the Citric Acid Cycle. 50. Quantitative Analysis of Vitamin C Contained in Foods. 51. Analysis of Vitamin A in Margarine. 52. Urine Analysis. APPENDICES. 1. List of Apparatus and Equipment in Student’s Locker. 2. List of Common Laboratory Equipment and Materials in the Laboratory. 3. Special Equipment and Chemicals.



TA B L E O F C O N T E N T S 1. Laboratory Techniques: Use of Laboratory Gas Burner; Basic Glassworking. 2. Laboratory Measurements. 3. Density Determination. 4.The Separation of the Components of a Mixture. 5. Resolution of Mixture by Distillation. 6. The Empirical Formula of a Compound: The Law of Constant Composition. 7. Determination of the Formula of a Metal Oxide. 8. Classes of Chemical Reactions. 9. Chemical Properties of Consumer Products. 10. Water Analysis. 11. Calorimetry: The Determination of the Specific Heat of a Metal. 12. Boyle’s Law: The Pressure-Volume Relationship of a Gas. 13. Charles’s Law: The Volume-Temperature Relationship of a Gas. 14. Properties of Gases: Determination of the Molecular Weight of a Volatile Liquid. 15. Physical Properties of Chemicals: Melting Point, Sublimation, and Boiling Point. 16. Entropy: A Measure of Disorder. 17. Solubility and Solution. 18. Water of Hydration. 19. Colligative Properties: Freezing Point Depression and Osmotic Pressure. 20. Factors Affecting Rate of Reactions. 21. Law of Chemical Equilibrium and Le Chatelier’s Principle. 22. pH and Buffer Solutions. 23. Analysis of Vinegar by Titrations. 24. Analysis of Antacid Tablets. 25. Measurement of Sulfur Dioxide Preservative in Foods. 26. Structure in Organic Compounds: Use of Molecular Models I. 27. Stereochemistry: Use of Molecular models II. 28. Identification of Hydrocarbons 29. Column and Paper Chromatography: Separation of Plant Pigments. 30. Identification of Alcohols and Phenols. 31. Identification of Aldehydes and Ketones. 32. Properties of Carboxylic Acids and Esters. 33. Properties of Amines and Amides. 34. Polymerization Reactions. 35. Preparation of Acetylsalicylic Acid (Aspirin). 36. Measurement of the Active Ingredient of Aspirin Pills. 37. Fermentation of a Carbohydrate: Ethanol from Sucrose. 38. Carbohydrates. 39. Preparation and Properties of Soap. 40. Preparation of Hand Cream. 41. Extraction and Identification of Fatty Acids from Corn Oil. 42. Analysis of Lipids. 43. TLC Separation of Amino Acids. 44. Acid-Base Properties of Amino Acids. 45.


BROOKS/COLE LABORATORY SERIES Allied Health/Health Sciences Chemistry: CER Course Suggestions

A L L I E D H E A LT H / H E A LT H S C I E N C E S C H E M I S T R Y TECHNIQUES TECH 231: Isolation (by Crystalization) and Identification of a Component of a Drug Mixture TECH 233: Melting Points of Organic Compounds TECH 244: Recrystallizing Salicylic Acid and Determining Its Purity TECH 380: Safety Practices in the Chemistry Laboratory TECH 381: The Gas Burner and Glass Working TECH 600: Practicing Safety in the Chemistry Laboratory TECH 601: Introducing Mass and Volume Measurements

MISCELLANEOUS MISC 153: Logarithms MISC 371: Introducing Graphic Techniques MISC 459: Naming Inorganic Compounds MISC 468: Radioactivity MISC 476: Interpreting and Balancing Chemical Equations MISC 490: Using Exponential Notation and Significant Figures MISC 614: Writing, Interpreting, and Balancing Chemical Equations MISC 873: Introduction to Computer-Based Graphical Analysis LabWorks (Windows) MISC 874: Introduction to Computer-Based Graphical Analysis TI83 Graphing Calculator MISC 875: Introduction to Computer-Based Graphical Analysis Vernier Graphical Analysis for Windows MISC 876: Introduction to Computer-Based Graphical Analysis Microsoft Excel 5 MISC 877: Introduction to Computer-Based Graphical Analysis Microsoft Excel 97

PROPERTIES PROP PROP PROP PROP PROP PROP PROP PROP PROP PROP PROP PROP PROP PROP PROP PROP

236: Aqueous Solutions 240: Structure and Properties of Alcohols 319: Preparing Soap and Determining Its Properties 374: Separating a Binary Mixture 383: Density of Liquids and Solids 384: Charles’s Law 385: Diffusion of Gases 391: Solutions 393: Studying Density Using Salad Oil and Vinegar 407: Determining the Molar Volume of Carbon Dioxide 454: Osmosis and Dialysis 474: Investigating Density, Miscibility, and Solubility 506: Fats, Oils, Soaps, and Detergents 602: Determining Density 603: Resolving a Two-Component Mixture 608: Calculating the Molar Volume of Carbon Dioxide

PROP 615: Studying Some Aspects of Solubility PROP 621: Isolating the Components of a Three-Component Mixture PROP 627: Observing Some Physical and Chemical Changes in Matter

REACTIONS REAC 389: Single Replacement Reactions and Relative Reactivity REAC 390: Double Replacement Reactions REAC 399: Detecting Signs of Chemical Change REAC 405: Identifying Six Solutions by Their Interaction REAC 444: Estimating the Optimum pH and Temperature for Digestive Enzyme Activity REAC 446: Qualitative Testing for Carbohydrates REAC 447: Qualitative Testing for Lipids REAC 448: Qualitative Tests for Amino Acids and Proteins REAC 469: Qualitative Tests for the OH Group in Organic Compounds REAC 472: Qualitative Tests for Alkenes REAC 604: Observing Signs of Chemical Reaction REAC 610: Observing Single Replacement Reactions REAC 611: Observing Some Double Replacement Reactions REAC 613: Classifying Some Chemical Reactions REAC 626: Observing Some Oxidation-Reduction Reactions

SYNTHESIS SYNT SYNT SYNT SYNT SYNT SYNT

439: Synthesizing Aspirin 451: Synthesizing Alum 470: Preparation and Identification of Esters 471: Isolating Caffeine from Tea 612: Preparing Alum 628: Preparing Aspirin


C O U R S E R E C O M M E N DAT I O N S

STOICHIOMETRY STOI 386: Determining the Empirical Formula of Copper Chloride STOI 606: Determining the Empirical Formula of Magnesium Oxide STOI 607: Reacting Baking Soda with Vinegar to Find Percent Acetic Acid

STRUCTURE STRC 435: Chemical Models: Ball-and-Stick Models of Organic Compounds STRC 467: Structural and cis-trans Isomerism in Carbon Compounds STRC 473: Molecular Structure and Optical Isomerism in Carbon Compounds continued on next page...



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BROOKS/COLE LABORATORY SERIES Allied Health/Health Sciences Chemistry: CER Course Suggestions

M O R E C O U R S E R E C O M M E N DAT I O N S A L L I E D H E A LT H / H E A LT H S C I E N C E S C H E M I S T R Y EQUILIBRIUM EQUL 392: Introducing Equilibrium EQUL 397: pH, Acids, and Bases EQUL 411: Estimating the pH of Household Products Using Red Cabbage Extract as an Indicator EQUL 465: Using Acid-Base Indicators to Visually Estimate the pH of Solutions EQUL 616: Introducing Chemical Equilibrium EQUL 617: Estimating the pH of Some Solutions Using Visual Indicators

ANAL 619: Titrating the Acetic Acid in Vinegar ANAL 620: Separating and Identifying FD&C Dyes Using Paper Chromatography ANAL 622: Analyzing the Vitamin C in Fruit Juices ANAL 624: Identifying Cations in a Solution ANAL 625: Estimating the Acid Content of Fruit Juices ANAL 638: Determining the Acid-Neutralizing Capacity of Common Antacids


THERMODYNAMICS THER THER THER THER THER THER THER

368: Heat of Neutralization 428: Estimating the Calorie Content of Nuts 609: Estimating a Heat of Neutralization 623: Estimating the Calorie Content of Peanuts 883: Heat of Neutralization Texas Instruments CBL System 885: Heat of Neutralization LabWorks Interface (Windows 95) 887: Heat of Neutralization Vernier Logger Pro for Windows

ANALYSIS ANAL 215: Dipeptide and Amino Acid Identification by Paper Chromatography ANAL 237: Physiologically Important Anions ANAL 238: Determining Ascorbic Acid in Vitamin C Tablets ANAL 239: Classifying Carbohydrates ANAL 241: Rennin Activity ANAL 242: DNA Extraction ANAL 394: Determining the Molar Concentration of a Sodium Hydroxide Solution ANAL 395: Titrating Vinegar ANAL 396: Introducing the Qualitative Analysis of a Group of Cations ANAL 426: Standardizing a Sodium Hydroxide Solution with a Standard Hydrochloric Acid Solution ANAL 427: Quantitatively Determining the Acid Content of Fruit Juices ANAL 445: Separation and Identification of Food and Drug Dyes by TLC ANAL 464: Comparing the Resistance of Buffered and Unbuffered Solutions to pH Change ANAL 478: Evaluating Commercial Antacids ANAL 483: Diagnosing Disease Using Kinetic Enzyme Assays ANAL 492: Separating and Identifying Food Dyes by Paper Chromatography ANAL 605: Determining the Percent Water in an Unknown Hydrate ANAL 618: Standardizing a Sodium Hydroxide Solution


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BROOKS/COLE LABORATORY SERIES General Chemistry

NEW FOR 2006!

Experiments in General Chemistry Featuring MeasureNet Bobby Stanton, Lin Zhu, and Charles H. Atwood — all of University of Georgia 456.pages | Paperbound | 9-1/2 x 11 | ©2006 | 0-534-42338-8

Laboratory Experiments in General Chemistry (Featuring MeasureNet) is the first self-directed laboratory manual to incorporate experiments conducted with MeasureNet—an innovative, network data collection system that introduces students to “real world” chemistry. With the new use of MeasureNet, experiments are more precise, only requiring small quantities of chemicals, making the lab safer and environmentally friendly. This laboratory manual is designed to first prepare students for the laboratory setting through conceptual and technique experiments. Students then work to solve a multi-component question, utilizing what they learned in previous experiments. Through this approach, and with the help of MeasureNet’s modern electronic data collection, analysis, and reduction, students truly prepare themselves for conducting chemistry in a professional setting!

KEY FEATURES Experiments allow students to spend less time collecting data and more time manipulating data and expressing their ideas and conclusions in formal writings, thereby creating a greater understanding and comprehension of the ideas, concepts, techniques, and theories presented in the text. With the new use of MeasureNet, experiments are more precise, only requiring small quantities of chemicals, making the lab safer and environmentally friendly. Experiments are self-directed and complement traditional concept/technique oriented experiments. This allows students to write their own experiments using the knowledge, skills, and techniques learned in performing concept/technique-oriented experiments in order to solve an assigned problem.

Substances. 3. Chromatography. 4. Determination of the Percent by Mass of the Components in a Mixture by Thermal Gravimetric Analysis. 5. Self Directed—Thermal Insulating Materials. 6. Reaction Stoichiometry. 7. Types of Chemical Reactions. 8. Identifying Metal Ions and Inorganic Compounds by their Chemical Interactions. 9. Gravimetric Analysis of a Chloride, Sulfate or Carbonate Compound. 10. Emission Analysis of Aqueous Solutions of Group IA and IIA Metal Salts. 11. Determination of Chromium (VI) Concentrations via Absorption Spectroscopy. 12. Determination of the Concentration of Acetic Acid in Vinegar. 13. Solubility, Polarity, Electrolytes and Nonelectrolytes. 14. Self-Directed— Determination of the Cause of a Fish-Kill in the Clark Fork of the Columbia River. 15. Self-Directed—Quality Control for the Athenium Baking Soda Company. 16. Gas Laws. 17. Colligative Properties. 18. Soaps and Detergents. 19. Heats of Chemical and Physical Processes. 20. Hess’s Law. 21. Determination of the Heat of Neutralization of a Variety of Strong Acids and Bases. 22. Dystan Medical Supply Company—Cold Packs and Hot Packs. 23. Kinetics—Reaction Orders. 24. Chemical Equilibria. 25. Determining the Equilibrium Constant for a Reaction. 26. Determining Ka of an Acid by Titration and from pH. 27. pH and Buffer Solutions. 28. Self-Directed—Identifying an Unknown Weak Acid.




GENERAL CHEMISTRY

TA B L E O F C O N T E N T S Safety Rules. Common Laboratory Glassware and Equipment. 1. Densities of Some Liquids and Solids. 2. Specific Heat of


11


NEW FOR 2006!

Lab Experiments for General Chemistry, 5e Toby F. Block and George M. McKelvy — both of Georgia Institute of


Technology

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508 pages | Paperbound | 8-1/2 x 10 3/4 | ©2006 | 0-534-42448-1

This established manual contains both classical experiments and “guided discovery” experiments in which students are given background information and are required to devise hypotheses, design procedures to test those hypotheses, evaluate their results, and to make suggestions for improving their work. Experiments are written to address students of various academic backgrounds and differing interests and abilities in chemistry. The experiments presented minimize the use of hazardous materials and provide detailed instructions on disposing of wastes. The Fifth Edition also allows experiments to be conducted in a conventional laboratory setting or with CBL-2 technology. While most experiments can be conducted in a single three-hour period, some have been designed to be completed over an extended time to illustrate that chemical systems do not work at an arbitrary schedule. Suggestions are provided for combining experiments of shorter length and similar pedagogy.

NEW TO THIS EDITION The Fifth Edition features three new experiments; “Using the Right Container, in the Right Manner,” “VSEPR,” and “Getting the End Point to Approximate the Equivalence Point.” The Fifth Edition suggests options for conducting some experiments with CBL-2 technology. Instructions for using spreadsheets in graphing are provided for each experiment. Expanded directions on calculations are provided for some experiments, where they are needed.

Data tables are updated and easy to read in order to facilitate teaching and learning. Students are given an introduction to the use of spreadsheets in presenting graphical data and preparing reports.

TA B L E O F C O N T E N T S 1. Using the Right Container, in the Right Manner. 2. On the Nature of Pennies. 3. Density. 4. VSEPR. 5. Separation of a Mixture into Its Components by Fractional Crystallization. 6. Fun with Solutions. 7. Properties of Oxides, Hydroxides and Oxo-Acids. 8. Volumetric Analysis: Acid/Base Titration Using Indicators. 9. Job’s Method: Determining the Stoichiometry of a Reaction. 10. The Synthesis of Cobalt Oxalate Hydrate. 11. The Synthesis of a Nitrite Complex. 12. Determination of the Composition of Cobalt Oxalate Hydrate. 13. The Gasimetric Analysis of a Nitrite Complex. 14. The Burning of a Candle. 15. The Vapor Pressure of Water. 16. Freezing-Point Depression. 17. Absorption Spectroscopy and Beer’s Law. 18. Getting the End Point to Approximate the Equivalence Point. 19. Determination of the Dissociation Constant of an Acid/Base Indicator. 20. Temperature Change and Equilibrium. 21. Analysis of Bleach for Hypochlorite Content. 22. Electrochemical Cells. 23. Enthalpy of Hydration of Ammonium Chloride. 24. Thermodynamic Prediction of Precipitation Reactions. 25. Kinetic Study of the Reaction between Iron (III) Ions and Iodide Ions. 26. Qualitative Analysis of Household Chemicals. 27. Analysis of a Soluble Salt. Appendices.



KEY FEATURES The experiments in this lab manual are extremely flexible and will work with a variety of books and curricula. Every chapter begins with objectives and procedures “in a nutshell” so that students are directed to focus on the significance of the experiments without getting lost in the procedures. Every experiment includes safety cautions, first aid, and disposal methods for using chemicals in a lab. Report sheets are included to help students clarify calculations of their experiments.



Chemical Principles in the Laboratory, 8e Emil Slowinski — Macalester College; Wayne C. Wolsey — Macalester College; and William L. Masterton — University of Connecticut 393 pages | Spiralbound | 8-1/2 x 11 | ©2005 | 0-534-42453-8

Chemical Principles in the Laboratory, Eighth Edition continues to build on its strengths by clearly presenting the basic principles of chemistry. The lab manual continues to maintain the high quality, time-tested experiments and techniques that have become hallmark features throughout the life of this title.

NEW TO THIS EDITION Most of the “Advance Student Assignments” (questions at the end of each experiment) have been revised. Experiment 5, “Identification of a Compound by Mass Relationships has been revised for clarity. Experiment 8, “Verifying the Absolute Zero of Temperature” features a new procedure that does not involve a mercury manometer. The Eighth Edition includes a new Experiment 15, “Vapor Pressure and heat of Vaporization of Liquids” that offers a better method for measuring vapor pressure. A new Experiment 19, “Molar Mass Determination by Depression of the Freezing Point,” uses water as the solvent for freezing point depression. The procedures for Experiment 25, “pH Measurements: Buffers and Their Properties,” and Experiment 42, “Rate Studies on the Decomposition of Aspirin,” have been simplified.

KEY FEATURES The direct approach of this laboratory manual has made it a “household” name in the General Chemistry laboratory market. Fully tested experiments have been consistently updated to maintain the integrity of this best-selling laboratory manual. Topics are presented clearly and the writing is user-friendly, while requiring students to read and demonstrate understanding of the material. Complete coverage of basic chemistry principles is provided. The “Advance Study Assignments” (ASA’s) provide students with sample questions, usually involving calculations that are similar to those required in processing the data obtained in each experiment. Students who complete the ASA’s prior


to coming to lab should have no trouble working up the data they actually observe in the lab session. Chemical Principles in the Laboratory is accompanied by a comprehensive Instructor’s Manual, available online at http://chemistry.brookscole.com. This password-protected Instructor’s Manual provides lab supervisors with equipment and reagent needs, as well as costs and sources where materials may be purchased. The Instructor’s Manual also includes sample calculations and solutions to all of the “Advance Study Assignment” questions, and comments and suggestions about each experiment.

TA B L E O F C O N T E N T S 1. The Densities of Liquids and Solids. 2. Resolution of Matter into Pure Substances, I. Paper Chromatography. 3. Resolution of Matter into Pure Substances, II. Fractional Crystallization. 4. Determination of a Chemical Formula. 5. Identification of a Compound by Mass Relationships. 6. Properties of Hydrates. 7. Analysis of an Unknown Chloride. 8. Verifying the Absolute Zero of Temperature—Determination of the Barometric Pressure. 9. Molar Mass of a Volatile Liquid. 10. Analysis of an Aluminum-Zinc Alloy. 11. The Atomic Spectrum of Hydrogen. 12. The Alkaline Earths and the Halogens: Two Families in the Periodic Table. 13. The Geometrical Structure of Molecules: An Experiment Using Molecular Models. 14. Heat Effects and Calorimetry. 15. Vapor Pressure and Heat of Vaporization of Liquids. 16. The Structure of Crystals—An Experiment Using Models. 17. Classification of Chemical Substances. 18. Some Nonmetals and Their Compounds—Preparations and Properties. 19. Molar Mass Determination by Depression of the Freezing Point. 20. Rates of Chemical Reactions, I. The Iodination of Acetone. 21. Rates of Chemical Reactions, II. A Clock Reaction. 22. Properties of Systems in Chemical Equilibrium—Le Chatelier’s Principle. 23. Determination of the Equilibrium Constant for a Chemical Reaction. 24. The Standardization of a Basic Solution and the Determination of the Molar M ass of an Acid. 25. pH Measurements: Buffers and Their Properties. 26. Determination of the Solubility Product of PbI2. 27. Relative Stabilities of Complex Ions and Precipitates Prepared from Solution s of Copper(II). 28. Determination of the Hardness of Water. 29. Synthesis and an Analysis of a Coordination Compound. 30. Determination of Iron by Reaction with Permanganate—A Redox Titration. 31. Determination of an Equivalent Mass by Electrolysis. 32. Voltaic Cell Measurements. 33. Preparation of Copper(I) Chloride. 34. Development of a Scheme for Qualitative Analysis. 35. Spot Tests for Some Common Anions. 36. Qualitative Analysis of Group I Cations. 37. Qualitative Analysis of Group II Cations. 38. Qualitative Analysis of Group III Cations. 39. Identification of a Pure Ionic Solid. 40. The Ten Test Tube Mystery. 41. Preparation of Aspirin. 42. Rate Studies on the Decomposition of Aspirin. 43. Analysis for Vitamin C. Appendix I: Vapor Pressure of Water. Appendix II: Summary of


NEW!

13

BROOKS/COLE LABORATORY SERIES General Chemistry Solubility Properties of Ions and Solids. Appendix III: Table of Atomic Masses (Based on Carbon-12). Appendix IV: Making Measurements-Laboratory Techniques. Appendix V: Mathematical Considerations-Making Graphs. Appendix VI: Suggested Locker Equipment. Appendix VII: Suggestions for Extension of the Experiments to “Real World Problems.”


ANCILLARIES

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Online Instructor’s Manual http://chemistry.brookcole.com General Chemistry Laboratory Notebook 50-page lab notebook for students 0-87540-246-1 100-page lab notebook for students 0-87540-247-X

NEW!

Laboratory Inquiry in Chemistry, 2e Richard Bauer — Arizona State University; James Birk — Arizona State University; and Doug Sawyer — Scottsdale Community College

258 pages | Spiralbound | 8-1/2 x 11 | ©2005 | 0-534-42424-4

Laboratory Inquiry in Chemistry, Second Edition provides a unique set of guided-inquiry investigations that focus on constructing knowledge about the conceptual basis of laboratory techniques, instead of simply learning techniques. By focusing on developing skills for designing experiments, solving problems, thinking critically, and selecting and applying appropriate techniques, the authors expose students to a realistic laboratory experience, typical of the practicing chemist. The Second Edition features six new experiments and is accompanied by a revised and updated Instructor’s Manual, available online. This new edition continues the proven three-phase learning cycle: exploration of chemical behaviors within the context of the problems posed; concept invention--the use of data and observations to construct accepted scientific knowledge about the concepts explored in the laboratory investigation; and, concept application--where students apply their conceptual understanding of the investigation at hand by modifying or extending the experiments, and write a report that emphasizes conceptual relevance. These college and honors level inquiry-based experiments correlate well with the recommended experiments outlined by the Advanced Placement Chemistry Development Committee.

NEW TO THIS EDITION “Experiment 15: How Can UV Sensitive Beads Be Used to Test Sunscreens?” Students are provided with sunscreens, labeled with different SPF values, to develop a protocol for using UV sensitive beads to test the sunscreens. They also study the UV protection of sunglasses. “Experiment 22: What Are the Structures of Some Alloys?” is a revision of former “Experiment 21: What Are the Structures of Some Crystalline Solids?” “Experiment 25: What Is the Molar Mass of Mars Ice Gas?” This is a typical gas law experiment that asks students to determine the molar mass of an unknown gas from ideal gas relationships. “Experiment 32: What Factors Affect the Solubility of Kidney Stones?” In this equilibrium investigation, students probe the solubility of calcium oxalate, the material composition of kidney stones. “Experiment 37: What is the pH of Soil?” Students test the pH of soil samples and experiment with different soil additives. “Experiment 44: What Formulation Makes the Best Toy?” Students conduct a polymer synthesis investigation of borax and glue by varying the proportion of each with water. “Experiment 48: How are Ionic Solids Identified?” This experiment extends the qualitative analysis investigations, in which students determine the identity of four ions that are present as a mixed solid sample that contains two ionic compounds. Based on reviewer and user feedback, additional experiments and the appendices have been revised to provide for a more complete lab program appropriate for a two-semester course. The new investigations help students relate the experimental applications to chemical concepts and to their own lives.

KEY FEATURES The investigations allow instructors flexibility in deciding how the experiments will be used. The investigations lend themselves to unguided inquiry, allowing students to creatively pursue solutions to the problems that are posed, while the Instructor’s Manual also provides help in using the investigations to guide students’ inquiry. The Instructor’s Manual provides information on how to use these experiments as part of the three-phase learning cycle. In the “exploration” phase, students explore chemical behaviors within the context of the problems posed. During the “concept invention” phase, students will use the data and observations to construct accepted scientific knowledge about the concepts being explored in the investigation. In the “concept application” phase, students apply their conceptual understanding of the investigation at hand by modifying or extending the experiments, and write a report that emphasizes conceptual relevance.



TA B L E O F C O N T E N T S 1. What Are the Safety Concerns in the Laboratory? 2. What’s in the Flask? 3. How Should Data Trends Be Presented? 4. How Is Lab Equipment Used? 5. What’s in the Bottles? 6. How Can the Waste Be Made Useful? 7. Is the Water Hard or Soft? 8. How Hot Is the Water? 9. Which Metal Will Burn the Skin? 10. Are All Neutralization Reactions the Same? 11. How Much Sodium Bicarbonate Is in the Mixture? 12. Is It Economical to Recycle Aluminum? 13. What Is a Copper Cycle? 14. Who Wrote the Ransom Note? 15. How Can UV Sensitive Beads Be Used to Test Sunscreens? 16. What Factors Affect the Intensity of Color? 17. How Much Cobalt Is in the Soil? 18. How Much Copper Is in the Coin? 19. Which Iron Compound Is It? 20. Should We Mine This Ore? 21. What Causes Intermolecular Attractions? 22. What Are the Structures of Some Alloys? 23. How Is LED Light Color Related to Composition? 24. What Is the Molar Mass of Mars Ice Gas? 25. Are Pollutant Gases Harmful to Plant Life? 26. How Much Gas is Produced? 27. Which Alcohols Are in the Barrels? 28. How Is Heat of Combustion Measured Indirectly? 29. What Is the Rate Law? 30. How Fast Does the Crystal Violet Decolorize? 31. Why Is the Vinegar Factory Rusting? 32. What Factors Affect the Solubility of Kidney Stones? 33. How Many Chemicals Are in the Vial? 34. What Factors Affect Chemical Equilibrium? 35. What Is the Formation Constant? 36. Are Household Items Acidic, Basic, or Neutral? 37. What is the pH of Soil? 38. What Is the Acid Dissociation Constant? 39. What Is the Solubility Product? 40. What Are Some Chemical Properties of Cream of Tartar? 41. What Are the Metals? 42. How Can a Battery Be Made from Coins? 43. What Is the Complex Ion? 44. What Formulation Makes the Best Toy? 45. How Are Anions Identified? 46. How


Are Cations Identified? 47. How Are More Cations Identified? 48. How Are Ionic Solids Identified?



Standard and Microscale Experiments in General Chemistry, 5e Carl B. Bishop and Muriel B. Bishop — both of Clemson University 600 pages | Paperbound | 8-1/2 x 11 | ©2004 | 0-534-42457-0

This comprehensive lab manual contains a wide array of experiments without sacrificing organizational clarity and includes categories on Energy, Kinetics, and Equilibrium. All experiments have undergone significant testing before being finalized, and many microscale experiments have been added to allow for more efficient and cost-effective means of conducting experiments.

NEW TO THIS EDITION The Fifth Edition includes a helpful reference correlation guide that links each experiment to corresponding topics in selected Brooks/Cole general chemistry textbooks. Several additional labs will be available online for instructors at http://chemistry.brookscole.com. The Fifth Edition is accompanied by a comprehensive Laboratory Instructor’s Manual, consisting of Important Reminders, Special Apparatus and Equipment, Chemicals, and Unknowns sections for each experiment. (available online at http://chemistry.brookscole.com.) Answers to Pre- and Post-Laboratory Assignments are available at the Brooks/Cole Chemistry Resource Center (http://chemistry.brookscole.com), as well as in a printed format available upon request


To help professors manage the implementation of this unique guided inquiry lab program, an Instructor’s Manual has been designed that contains models for assessment, comprehensive suggested prompts for classroom discussion throughout each investigation, and TA training material. A scenario that begins each investigation puts real-life spin on the problem at hand, provides students with a sense of why the project is relevant, and creates a scenario that is comparable to what chemists face. A list of goals to address as they perform the investigation is provided to students so their attention is focused on the desired outcomes. A list of materials and reagents is provided, limiting students to particular experimental techniques. The “Getting Started” section of each investigation provides guidelines or hints that help students design their experiments. A contribution form is provided at the conclusion of each lab to encourage students to supply information about how they helped their group complete the investigation and write its report.

KEY FEATURES Standard and Microscale Experiments in General Chemistry is noted for its strong emphasis on safety procedures and precision, which leads to a successful laboratory experience for students. Pre-Laboratory Questions help students understand the chemical principles before beginning the experiments.

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The Background feature precedes groups of experiments to help students associate theory with experiments. Report Forms allow space for observations and interpretations. Post-Laboratory Questions are designed to be answered during the experiment and can be removed for grading. The large quantity of micro-scale experiments ensures that instructors have a wide-ranging selection and allow for more efficient and cost-effective means of conducting experiments. The flexible organization allows for ease of use with a variety of texts and accommodates a wide variety of curricula.

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TA B L E O F C O N T E N T S PART 1: EQUIPMENT. A. Common Laboratory Safety Equipment. B. Common Laboratory Glassware. C. Common Equipment. PART 2: LABORATORY TECHNIQUES. A. Handling Chemicals / Solids / Liquids. B. Determination of Mass and Weight / Triple-Beam and Platform Balances / Toploading Balances. C. Volumetric Techniques—The Measurements of Volume / Graduated Cylinders / Volumetric Pipets / Burets and Titration Procedures / Volumetric / Flasks. D. Laboratory Gas Burner. E. Heating And Evaporating Liquids. F. Separation Techniques / Gravity Filtration / Vacuum Filtration / Use of Centrifuges. G. Ignition of Crucible and Precipitates. H. Working and Handling Glass / Cutting Glass / Fire Polishing Glass / Bending Glass / Inserting Glass Tubing, Thermometers, and Funnel Stems into Corks and Rubber Stoppers. I. Collecting Gases / Testing for Odor / Collection for Gases / An Improvised Fume Hood. J. Spectrophotometer / Calibration and Use of Spectrophotometer / Measurements of Sample. K. Treatment of Experimental Data / Significant Figures / Report Average Values. L. pH Meter. M. Melting And Boiling Determination / Melting Point Determination / Boiling Point Determination / An Exercise in Chemical / Safety and Laboratory Rules. PART 3: EXPERIMENTS (*MICRO EXPERIMENTS). I. Background: Review of Simple Mathematics (Experiment 1). 2. Density of Solids and Liquids: Mass/Volume Measurements. 3. Indirect Gravimetric Determination of a Hydrated Compound in a Mixture. 4. Percent Copper and Formula Weight of a Copper Compound 65. II: BACKGROUND: SOLUTIONS, SOLUBILITY AND SEPARATION TECHNIQUES. 5. Solubilities. 6. Separation of the Components of a Mixture. 7. Chromatography. III: BACKGROUND: CHEMICAL REACTIONS IN AQUEOUS SOLUTIONS AND SYNTHESES. 8. Hydrogen Ions, pH, and Indicators. 9. Identify Eight Metal Ions by Reactions with Anions. 10. Identify Ten Inorganic Compounds by Their InterChemical Reactions. 11. The Formula of a Precipitated Compound. 12. A Sequence of Chemical Reactions. 13. Synthesis of a Compound (Alum) from Scrap Aluminum. IV: BACKGROUND: PERIODIC TABLE AND PERIODICITY. 14. Molecular Models: Lewis Dot Formulas, VSEPR Theory, and Valence Bond Theory. 15. Chemical Periodicity of the Halide

Ions. 16. Relative Reactivity of Metals and the Activity Series. V: BACKGROUND: MOLE, MOLECULAR WEIGHT AND GAS LAWS. 17. Indirect Determination of the Masses of Pieces of Magnesium. 18. Density of Gases. 19. The Molecular Weight of a Volatile Compound. 20. Standard Molar Volume of a Gas. VI: COLLIGATIVE PROPERTIES. 21. The Molecular Weight of a Compound by Freezing Point Depression Measurement. VII: BACKGROUNDS: ACIDS-BASES. 22. Acid Base Titration Curves Using: I. An Indicator Color-Reference II. Micro-pH Meter (micro-scale). 23. Acid Base Titrations: Analysis of Acid Solutions of Unknown Concentrations (macro-scale). 24. Action of Antacid Tablets. VIII: BACKGROUND: REDUCTION-OXIDATION REACTIONS. 25. Voltaic and Electrolytic Cells. 26. Reduction-Oxidation Titrations (both micro and macro). IX: BACKGROUND: ENERGY / EXPERIMENT. 27. Heat Energy Associated with Chemical and Physical Changes. 28. Heats of Neutralization and Hess’ Law. X: BACKGROUND: KINETICS. 29. Factors that Influence the Rates of Reaction. 30. Rates of Chemical Reactions. XI: BACKGROUND: EQUILIBRIUM. 31. Chemical Equilibrium—An Introduction. 32. Spectrophotometric Determination of an Equilibrium Constant. 33. The Spectrophotometric Determination of the Formula for a Complex Species. 34. Solubility Products of Insoluble Salts. 35. Determination of Ka from Measurements of pH. XII: BACKGROUND: DESCRIPTIVE CHEMISTRY. 36. Oxygen and Some Oxides. 37. Nitrogen and Its Compounds 38. The Anions of Sulfur. XIII: BACKGROUND: INTRODUCTION TO ORGANIC CHEMISTRY. 39. Organic Qualitative Analysis. 40. Commercial Esters—Aspirin and Oil of Wintergreen. 41. Polymers / Experiment. 42. Preparation and Properties of Soaps: Properties of Detergents. Appendices. A: Logarithms and pH. B: Formulas, Ionic Charges and Names for Some Common Ions. C: Classification of Acids. D: Classification of Bases. E: Solubility Rules for Common Inorganic Compounds. F: Vapor Pressure of Water Near Room Temperature. G: Molecular and Ionic Chemical Equations. H: Concentrations and Primary Standards. I: Units of Measurement.





Experiments in General Chemistry, 4e Steven Murov — Modesto Junior College 465 pages | Paperbound | 8-1/2 x 11 | ©2004 | 0-534-42462-7

Experiments in General Chemistry, Fourth Edition, has been designed to stimulate curiosity and insight, and to clearly connect lecture and laboratory concepts and techniques. To accomplish this goal, an extensive effort has been made to develop experiments that maximize a discovery-oriented approach and minimize personal hazards and ecological impact. Like earlier editions, the use of chromates, barium, lead, mercury, and nickel salts has been avoided. The absence of these hazardous substances should minimize disposal problems and costs. This lab manual focuses not only on what happens during chemical reactions, but also helps students understand ‘why’ chemical reactions occur. The sequence of experiments has been refined to follow topics covered in most general chemistry textbooks. In addition, Murov has included a correlation chart that links the experiments in the manual to the corresponding chapter topics in several Brooks/Cole general chemistry titles. Each experiment—framed by pre-and post-laboratory exercises and concluding thought-provoking questions—helps to enhance students’ conceptual understanding.

NEW TO THIS EDITION The sequence of experiments has been refined to follow topics covered in most general chemistry textbooks. The Fourth Edition features a correlation chart that links the experiments in the manual to the corresponding chapter topics in several Brooks/Cole general chemistry titles. Optional Internet exercises have been added to several experiments, providing students with the opportunity to expand their learning online. Enhanced exercises and new experiment features. The Fourth Edition includes a new experiment on the topic of equilibrium. A procedure for following the visual clock reaction spectroscopically, instead of visually, has been added to the kinetics experiment. This also provides a link between the equilibrium and kinetics experiments. Carefully revised to reinforce and clarify the connections made between experiments, the Fourth Edition enhances students’ conceptual understanding of key chemical principles and concepts.


As with previous edition, the use of chromates, barium, lead, mercury, and nickel salts has been avoided, effectively minimizing disposal problems and decreasing costs. Murov focuses not only on what happens during chemical reactions, but also helps students understand ‘why’ chemical reactions occur. Each experiment includes pre-laboratory exercises (with answers to selected questions included) and thought-provoking questions. A number of experiments include post-laboratory exercises and the manual concludes with a set of review exercises. Review Exercises, found at the end of the manual, help students test their understanding of key concepts and synthesize the material they have learned. iancillaries

TA B L E O F C O N T E N T S Safety First. 1. Early Explorations and Terminology. 2. Separation of Mixtures. 3. Measurements and Identification Techniques. 4. Density, Accuracy, Precision and Graphing. 5. Classification of Chemical Reactions. 6. Quantitative Precipitation. 7. Empirical Formula of a Hydrate. 8. Electrical Conductivity and Chemical Bonding. 9. Ionic Reactions. 10. Activities of Metals. 11. Quantitative Solution Chemistry. 12. Gas Law Studies. 13. Thermochemistry. 14. Periodicity and Properties of Elements and Compounds: An Internet Study. 15. Spectroscopy of Cobalt (II) Ion. 16. Lewis Structures and Molecular Models. 17. Molecular Polarity and Chromatography. 18. Synthesis of Copper (II) Glycinate. 19. Standardization of Thiosulfate. 20. Analysis of Bleach and Copper (II) Glycinate. 21. Cooling Curves and Crystal Structures. 22. Water Purification and Analysis. 23. Acids and Bases: Reactions and Standardization. 24. Acids and Bases: Analysis. 25. Acids and Bases: pH Measurements. 26. Acids and Bases: Carbonate Analysis. 27. Solubility Product. 28. Complexes. 29. Rates and Mechanisms of Reactions. 30. Redox Reactions. 31. Electrochemistry. 32. Organic Models and Isomerism. 33. Spectroscopic Analysis of Aspirin. 34. Polymers and Some Fun. Epilogue. Appendixes.




KEY FEATURES

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Laboratory Handbook for General Chemistry, 2e

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Norman E. Griswold — Nebraska Wesleyan College; H.A. Neidig — Lebanon College; James N. Spencer — Franklin and Marshall College; and Conrad L. Stanitski — University of Central Arkansas 80 pages | Paperbound | 8-1/2 x 11 | ©2002 | 0-534-97694-8

To do a chemistry lab experiment students need to know how to use the equipment and to perform basic laboratory procedures, such as weighing and making volume measurements. This handbook is designed to be an affordable, “how to” guide to basic techniques, operations, and equipment used in general chemistry laboratory courses. The handbook can be used in conjunction with CER modular experiments, to support locally-written experiments, or to complement the techniques sections of commercial lab manuals.

KEY FEATURES A user-friendly design and layout keeps figures and related text together. Excellent illustrations represent equipment and operations. End-of-chapter review and test questions. Chapter 1, the safety chapter, reflects the current thinking about lab safety. Use of plotting programs is discussed in the graphing chapter. An expanded mathematical operations chapter (Chapter 12). Use of pH meters is presented in Chapter 10. Emphasis is on the practical. Explanations are succinct and to the point. Heavy use is made of illustrations. The laboratory safety chapter concludes with a laboratory safety agreement for students to sign and hand in, plus a laboratory safety quiz. Illustrations and names of general laboratory equipment and glassware also include the purpose and use of each item. Most commonly used reference tables are included in the Appendix. Additional sheets of graph paper are included at the back of the book.

Laboratory Safety Agreement / Laboratory Safety Quiz. 2. Glassware and General Equipment. Questions Related to Laboratory Equipment. 3. Weighing. Using a Top-loading Balance / Using a Triple Beam Balance / Using an Analytical Balance / Questions Regarding Weighing. 4. Measuring Liquid Volumes. Graduated Cylinders / Pipets / Using Volumetric Pipets / Burets / Volumetric Flasks / Questions Regarding Measuring Liquid Volumes. 5. Transferring Materials. Transferring Solids / Transferring Liquids / Using Pipets NonQuantitatively / Mixing Liquids / Mixing a Solid and a Liquid / Questions Regarding Transferring Materials. 6. Heating Sources and Techniques. Bunsen Burner / Microburners / Hot Plate / Heating a Liquid / Heating Crucibles / Questions Regarding Heating Sources and Techniques. 7. Separations. Decantation / Filtering / Gravity Filtration: Using a Conical Funnel / Suction Filtration: Using a Büchner Funnel / Centrifuging to Separate a Precipitate from Solution / Questions Regarding Separations. 8. Small-Scale Operations. Small-Scale Equipment / Heating Small-Scale Equipment / Questions Regarding Small-Scale Operations. 9. Visible Spectrophotometers. Questions Regarding a Spectronic 20. 10. Using a pH Meter. Questions Regarding Using a pH Meter. 11. Keeping a Laboratory Notebook. 12. Mathematical Operations. Exponential Notation / Expressing Numbers Using Exponential Notation / Exponential Notation Using a Calculator / Questions Regarding Exponential Notation / Significant Figures / Significant Figures in Addition and Subtraction / Significant Figures in Multiplication and Division / Questions Regarding Significant Figures / Rounding Off Numbers / Rounding Off Calculated Results / Dealing with Measurement Errors / Standard Deviation / Equation and Slope of a Straight Line. 13. Representing Data and Results Using Graphs. Graphs / Graphing Programs / Graphing Exercise. Appendix A. Operations with Glass / Cleaning Glassware / Working with Glass Tubing / Cutting Glass Tubing / Firepolishing Glass Tubing / Bending Glass Tubing / Preparing Glass Droppers or Pipets. Appendix B. Reference Tables / Physical Constants / Conversion Tables / Common Acids and Bases / Solubility Rules / Vapor Pressure and Temperature Data / Standard Reduction Potentials, Eo / Acid Ionization Constants, Ka / Base Ionization Constants, Kb / Solubility Product Constants, Ksp. Appendix C. General Laboratory / References. Index.

TA B L E O F C O N T E N T S 1. Safety in the Laboratory. General Safety Rules / Material Safety Data Sheets (MSDS) / Disposal of Materials / Inserting Glass into Corks or Rubber Stoppers / Fire Safety / Chemistry


BROOKS/COLE LABORATORY SERIES General Chemistry: CER Course Suggestions

GENERAL CHEMISTRY TECHNIQUES TECH TECH TECH TECH TECH TECH TECH TECH TECH TECH TECH TECH

316: Filtrations 363: Qualitative Inorganic Analysis Techniques 380: Safety Practices in the Chemistry Laboratory 381: The Gas Burner and Glass Working 382: Transfer and Measurement of Chemicals 430: Safety Precautions 485: Measuring Mass 488: Making and Using Visible Absorption Measurements 489: Using a pH Meter 511: Laboratory Techniques: Measuring the Volume of Liquids 600: Practicing Safety in the Chemistry Laboratory 601: Introducing Mass and Volume Measurements

MISCELLANEOUS MISC 153: Logarithms MISC 371: Introducing Graphic Techniques MISC 408: Representing Data Graphically MISC 457: Balancing Oxidation-Reduction Equations Using the Oxidation Number Method MISC 458: Balancing Oxidation-Reduction Equations Using the IonElectron Method MISC 459: Naming Inorganic Compounds MISC 477: Writing and Balancing Chemical Equations MISC 486: Dimensional Analysis MISC 490: Using Exponential Notation and Significant Figures MISC 521: Using Statistics to Analyze Experimental Data MISC 873: Introduction to Computer-Based Graphical Analysis LabWorks (Windows) MISC 874: Introduction to Computer-Based Graphical Analysis TI83 Graphing Calculator MISC 875: Introduction to Computer-Based Graphical Analysis Vernier Graphical Analysis for Windows MISC 876: Introduction to Computer-Based Graphical Analysis Microsoft Excel 5 MISC 877: Introduction to Computer-Based Graphical Analysis Microsoft Excel 97

PROPERTIES PROP 041: A Study of the Molal Freezing Point Constant of Water PROP 319: Preparing Soap and Determining Its Properties PROP 332: Evaluation of the Gas Law Constant PROP 344: Molecular Mass Determination by Freezing Point Depression in t-Butyl Alcohol PROP 353: Statistical Analyis of Experimental Density Data PROP 362: Evaluation of 0 K PROP 377: Determining the Molar Volume of Oxygen PROP 379: Determining the Proportionality Constant, R, in the Ideal Gas Equation PROP 383: Density of Liquids and Solids PROP 410: Studying Boyle’s Law PROP 421: Determining the Solubility of an Unknown Salt at Various Temperatures PROP 440: Identifying a Liquid Using Physical Properties PROP 461: Separating and Isolating the Components of a Ternary System PROP 474: Investigating Density, Miscibility, and Solubility PROP 481: Determining the Molar Mass of a Volatile Liquid by the Dumas Method PROP 495: Classifying Matter by Properties PROP 500: Determining Molar Mass by Freezing Point Depression PROP 506: Fats, Oils, Soaps, and Detergents PROP 507: Determining Molar Mass by Freezing Point Depression in Naphthalene PROP 513: Separating and Isolating the Major Components of Milk PROP 515: Using Density to Determine the Sugar Content in Commercial Beverages PROP 516: Identifying a Solid by Its Density PROP 518: Separating and Recovering the Components of a Ternary Mixture PROP 522: Determining the Molar Mass of CO2 PROP 524: Studying the VolumeTemperature Relationship of a Gas PROP 530: Forces Holding a Protein Together PROP 602: Determining Density PROP 878: Molar Mass Determination by Freezing Point Depression Texas Instruments CBL System PROP 880: Molar Mass Determination by Freezing Point Depression LabWorks Interface (Windows 95) PROP 882: Molar Mass Determination by Freezing Point Depression Vernier Logger Pro for Windows



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M O R E C O U R S E R E C O M M E N DAT I O N S GENERAL CHEMISTRY REACTIONS REAC 321: Determining the Effects of Acid Rain REAC 406: Writing Chemical Equations and Identifying Unknown Solutions Using Microscale Techniques REAC 456: Studying Oxidation-Reduction Reactions REAC 480: A Sequence of Chemical Reactions: Transforming Copper REAC 482: Copper From Start to Finish: A Sequence of Chemical Reactions REAC 502: Establishing the Relative Reactivity of Halogens and Halide Ions REAC 539: Writing Chemical Equations Based on Observation of Reactions REAC 908: Identifying Solutions by Observing Chemical Reactions


SYNTHESIS SYNT 095: Preparation and Analysis of a Coordination Compound SYNT 341: Synthesis of Strontium Iodate Monohydrate SYNT 347: Preparation of Strontium Iodate Monohydrate SYNT 431: Preparing Tris(2,4-pentanedionato)iron(III), an Iron Coordination Complex SYNT 432: Preparing Tetraaminecopper(II) Sulfate Monohydrate SYNT 433: Synthesizing and Anlalyzing a Coordination Compound of Nickel(II) Ion, Ammonia, and Chloride Ion SYNT 439: Synthesizing Aspirin SYNT 452: Synthesizing Alum and Observing Some Chemistry of Aluminum SYNT 540: Synthesizing Alum and Determining Chemical Properties of Aluminum and Alum SYNT 907: Applying the Concept of a Limiting Reactant to the Synthesis of Aspirin

STOICHIOMETRY STOI 003: Stochiometry of the Lead(II) Nitrate-Potassium HalideWater System STOI 007: Stochiometry: Mole Ratio Study STOI 301: Determination of the Formula of a Chemical Compound STOI 315: Synthesis of Lead(II) Chromate STOI 369: The Reaction of Magnesium with Hydrochloric Acid STOI 386: Determining the Empirical Formula of Copper Chloride STOI 388: The Empirical Formula of an Oxide STOI 398: Determining the Empirical Formula of a Compound Containing STOI 401: Studying the Stoichiometry of the Reaction of Nickel(II) Ion and Hydroxide Ion Using Microscale Techniques STOI 420: Precipitating Lead Chromate on a Small Scale

STOI 423: Determining the Empirical Formula of a Compound STOI 438: Determining the Formula and Estimating the Dissociation Constant of a Complex Ion STOI 475: Determining the Composition of a Cobalt(II) Nitrate Sample by Visible Spectrophotometry STOI 496: Approximating Avogadro’s Number Using Glass Beads and Monomolecular Film STOI 497: Reacting Vinegar with Baking Soda STOI 509: Determining the Formulas of Copper(II)Ethylenediamine Complex Ions by Spectrophotometry STOI 514: Calculating Avogadro’s Number of Comparing Atoms and Oranges STOI 520: Determining the Empirical Formula of Magnesium Oxide STOI 525: Determining the Empirical Formula of Zinc Chloride STOI 903: Determining Reaction Stoichiometry by Continuous Variations STOI 906: Determining Hydrogen Peroxide Content by Gas Stoichiometry

STRUCTURE STRC STRC STRC STRC STRC

345: The Visible Atomic Spectrum of Hydrogen 351: Models and the Crystalline State 409: Molecular Geometry and Bonding 434: Writing Lewis Symbols and Lewis Structures 449: Determining Atomic Emission by Spectroscopy

KINETICS KINE 429: Studying the Kinetics of the Solvolysis of 2-Chloro-2-methylpropane KINE 504: Determining the Rate Law for the Crystal Violet-Hydroxide Ion Reaction KINE 505: Studying the Rate of Reaction KINE 508: Studying the Kinetics of a Chemical Reaction

EQUILIBRIUM EQUL 308: Solubility Product Constant of Lead(II) Iodide EQUL 342: Determination of the Solubility Product Constant of a Salt EQUL 343: Determining an Equilibrium Constant Using Spectroscopy EQUL 376: Determining the Dissociation Constant of a Weak Acid Using pH Measurements EQUL 392: Introducing Equilibrium EQUL 400: Estimating the Solubility Product Constant of Strontium Iodate Using Microscale Techniques EQUL 402: Evaluating the Dissociation Constant of a Weak Acid Using Microscale Techniques EQUL 404: Studying Chemical Equilibria and Applying Le Chatelier’s Principle Using Microscale Techniques


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GENERAL CHEMISTRY EQUL 441: Evaluating the Equilibrium Constant EQUL 443: Studying the Effects of Buffering on the Resistance of a Solution to pH Change EQUL 453: Determining the Equivalent Mass and Dissociation Constant of an Unknown Weak Acid by Titrimetry EQUL 487: Determining the Common Ion Effect on the Solubility of Potassium Hydrogen Tartrate EQUL 494: Monitoring Acid–Base Titrations with a pH Meter EQUL 499: Studying the pH of Strong Acid, Weak Acid, Salt, and Buffer Solutions EQUL 519: Determining the pKa of an Acid-Base Indicator EQUL 526: Equilibrium between Two Coordinations of Co2+ in a Solution EQUL 616: Introducing Chemical Equilibrium EQUL 853: Identifying a Weak Acid by Titrimetry Texas Instruments CBL System EQUL 855: Identifying a Weak Acid by Titrimetry LabWorks System (Windows 95) with Manual Volume Entry EQUL 857: Identifying a Weak Acid by Titrimetry Vernier Logger Pro for Windows EQUL 859: Identifying a Weak Acid by Titrimetry LabWorks System (Windows) with a Drop Counter EQUL 865: Acid-Base Titration Curves Texas Instruments CBL System EQUL 867: Acid-Base Titration Curves LabWorks System (Windows) with Manual Volume Entry EQUL 869: Acid-Base Titration Curves Vernier Logger Pro System (Windows) EQUL 871: Acid-Base Titration Curves LabWorks System (Windows) with a Drop Counter

THERMODYNAMICS THER 074: Heat of Reaction of Magnesium and Hydrochloric Acid THER 185: Enthalpy of Formation of Ammonium Salts THER 303: Enthalpy of Formation THER 346: Enthalpy of Neutralization THER 368: Heat of Neutralization THER 370: Enthalpy of Hydration THER 428: Estimating the Calorie Content of Nuts THER 512: The Thermodynamics of KNO3 Dissolving in Water THER 529: Determining the Thermodynamics of Ca(OH)2 Solubility in Water THER 609: Estimating a Heat of Neutralization THER 860: Determining Enthalpy of Neutralization Texas Instruments CBL System THER 862: Determining Enthalpy of Neutralization LabWorks System (Windows) THER 864: Determining Enthalpy of Neutralization Vernier Logger Pro System (Windows) THER 883: Heat of Neutralization Texas Instruments CBL System

THER 885: Heat of Neutralization LabWorks Interface (Windows 95) THER 887: Heat of Neutralization Vernier Logger Pro for Windows THER 901: Temperature Change, Heat of Reaction, and Enthalpy Change of Neutralization Reactions

ELECTROCHEMISTRY ELEC 224: Determination of the Molecular Mass of Lead by Electrolysis ELEC 418: Studying Electrochemical Cells and Reduction Potentials ELEC 419: Studying Electrochemistry and Establishing the Relative Reactivity of a Series of Metals ELEC 450: Studying Electrochemical Half-Cells and Half-Reactions ELEC 510: Studying the Temperature Dependence and Thermodynamics of Electrochemical Cells ELEC 905: Devising a Reduction Potential Table

ANALYSIS ANAL 304: Evaluation of Vinegar Samples ANAL 322: Determining Aluminum(III) Concentration in Natural Water ANAL 335: Analysis of Hydrogen Peroxide ANAL 349: Standardizing a Hydrochloric Acid Solution ANAL 350: Standardizing a Sodium Hydroxide Solution ANAL 356: Gravimetric Determination of Sulfate ANAL 357: Spectrophotometric Determination of Copper in Brass ANAL 358: A Beer’s Law Study ANAL 359: Spectrophotometric Analysis of Permanganate Solutions ANAL 360: A Colorimetric Determination of Aspirin in Commercial Preparations ANAL 361: Spectrophotometric Studies of Food Dye Solutions ANAL 364: The Chemistry and Qualitative Analysis of Cations: Group Separations and Separations of Group I Cations ANAL 365: The Chemistry and Qualitative Analysis of Cations: Group II ANAL 366: The Chemistry and Qualitative Analysis of Cations: Group III and IV ANAL 367: The Chemistry and Qualitative Analysis of Anions ANAL 378: Determining the Percent Composition of an Aqueous Hydrogen Peroxide Solution ANAL 394: Determining the Molar Concentration of a Sodium Hydroxide Solution ANAL 395: Titrating Vinegar ANAL 403: Estimating the Copper Content of Malachite Using Microsale Techniques ANAL 415: Introducing Volumetric Techniques by Analyzing Bleaching Solution



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GENERAL CHEMISTRY ANAL 416: Determining the Percent Sodium Hypochlorite in Commercial Bleaching Solutions ANAL 417: Using Volumetric Glassware to Measure, Dilute, and Titrate an Acid Solution ANAL 424: Standardizing a Sodium Hydroxide Solution with Oxalic Acid ANAL 425: Titrating Hydrochloric Acid Solution with a Standard Sodium Hydroxide Solution ANAL 426: Standardizing a Sodium Hydroxide Solution with a Standard Hydrochloric Acid Solution ANAL 427: Quantitatively Determining the Acid Content of Fruit Juices ANAL 436: Determining Water Hardness by Edta Titration ANAL 437: Evaluating the Calcium Ion Content in Commercial Dried Milk Powders ANAL 442: Analyzing Food Products for Vitamin C ANAL 455: Separating and Determining the Mass of Calcium Ion in a CalciumEnriched Tablet ANAL 462: Nonsulfide Qualitative Analysis ANAL 463: Nonsulfide Qualitative Analysis of Cations: Separating and Identifying Representative Group A Cations (Hg22+, Ag+, and Pb2+) ANAL 466: Standardizing a Sodium Hydroxide Solution and Using it to Analyze Vinegar ANAL 478: Evaluating Commercial Antacids ANAL 479: Determining the Formula of an Ionic Hydrate Gravimetrically ANAL 492: Separating and Identifying Food Dyes by Paper Chromatography ANAL 493: Analyzing a Mixture of Sodium Hydrogen Carbonate and Sodium Chloride by Thermal Decomposition ANAL 498: Separating Selected Metal Cations by Paper Chromatography ANAL 501: Determining the Effects of Cooking on the Vitamin C Content of Green Pepper ANAL 503: Nine Bottles: An Adventure in Chemical Identification ANAL 517: Determining the Water Content of an Ionic Hydrate ANAL 523: Qualitative Analysis of Cations ANAL 618: Standardizing a Sodium Hydroxide Solution ANAL 619: Titrating the Acetic Acid in Vinegar ANAL 900: Determining Dolomite Composition by Thermal Decomposition ANAL 902: Analysis of the Acetic Acid Content of Vinegar ANAL 904: Separating the Components of Beach Sand ANAL 909: Determining the Thickness of Zinc on Galvanized Washers


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BROOKS/COLE LABORATORY SERIES Organic Chemistry

NEW!

Introduction to Organic Laboratory Techniques: A Small Scale Approach, 2e Donald L. Pavia, Gary M. Lampman, George S. Kriz, and Randall G. Engel — all of Edmonds Community College 1,019 pages | Casebound | 8 x 10 | ©2005 | 0-534-40833-8

In this laboratory textbook for students of organic chemistry, experiments are designed to utilize standard-scale (“macroscale”) glassware and equipment but with smaller amounts of chemicals and reagents. The textbook features a large number of traditional organic reactions and syntheses, as well as the isolation of natural products and experiments with a biological or health science focus. The organization of the text is based on essays and topics of current interest. There are six introductory technique-based experiments and eleven projectbased experiments. In addition, there is a section of green chemistry experiments. The book contains a comprehensive treatment of laboratory techniques, including small-scale and some microscale methods.

NEW TO THIS EDITION New, techniques-based experiments are used as the first, introductory experiments to appeal to those situations where instructors do not want to jump immediately into advanced material. New technique experiments include: Experiment 1, “Solubility;” Experiment 2, “Crystallization;” Experiment 3, “Extraction;” Experiment 4, “Chromatography;” Experiment 5, “Simple and Fractional Distillation;” and, Experiment 6, “Infrared Spectroscopy and Boiling Point Determination.” Several of these experiments conclude with “Critical Thinking Applications”--short exercises in which students must provide experimentally determined solutions to problems related to the techniques and the underlying principles. The Second Edition features a new essay, “Green Chemistry,” and two new green chemistry experiments: Experiment 31, “Chiral Reduction of Ethyl Acetoacetate: Optical Purity Determination;” and, Experiment 32, “Nitration of Aromatic Compounds Using a Recyclable Catalyst.” The authors have included a new section of project-based experiments that features: Experiment 57, “A Separation and Purification Scheme;” Experiment 60, “The Analysis of


Antihistamine Drugs by Gas Chromatography-Mass Spectrometry;” Experiment 62, “The Aldehyde Enigma;” Experiment 63, “Synthesis of Substituted Chalcones: A Guided-Inquiry Experience;” and, Experiment 66, “An Oxidation Puzzle.” In all of these experiments, students must either solve a significant problem or they must generate all or part of a procedure. Intended to promote critical thinking, these experiments not only challenge students, but also give them a feeling of what it is like to “do” research in chemistry. New exercises involving molecular modeling and computational chemistry have been added to several experiments. The Second Edition features a reorganization of the technique chapters to more closely match the order in Microscale and Macroscale Techniques in the Organic Laboratory. This new edition also includes three new technique chapters: Technique 4, “How to Find Data for Compounds: Handbooks and Catalogues;” Technique 10, “ Solubility;” and, Technique 28, “Mass Spectrometry.” In addition, several technique chapters have been extensively revised and update.

KEY FEATURES The textbook contains a variety of small-scale experiments using standard-scale (macroscale) glassware and equipment. Essays and examples on contemporary topics are provided to spark student interest and engage them in the learning process. Green chemistry has been introduced as it’s become an important topic to share with students. Experiments are well-written, comprehensive, and pre-tested. Infrared, proton NMR, and 13C NMR spectroscopy is incorporated into many experiments. Some experiments also have an option to use gas chromatography-mass spectrometry. For discovery-based learning needs, open-ended experiments are provided to allow students to “write” their own experimental procedures and make their own discoveries. Molecular modeling experiments give students an opportunity to experience the power of molecular modeling software. “Caution” boxes emphasize careful handling of chemicals and the importance of safety in the laboratory. Clear and accurate diagrams of laboratory set-ups increase students’ confidence in setting up a lab. End-of-chapter problems test students’ mastery of the material.


ORGANIC CHEMISTRY

TA B L E O F C O N T E N T S Part I: INTRODUCTION TO BASIC LABORATORY TECHNIQUES. Experiment 1. Solubility. Experiment 2. Crystallization. Experiment 3. Extraction. Experiment 4. Chromatography. Experiment 5. Simple and Fractional Distillation. Experiment 6. Infrared Spectroscopy and BoilingPoint Determination. Essay: Aspirin. Experiment 7. Acetylsalicylic Acid. Essay: Analgesics. Experiment

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Organic Chemistry

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8. Acetanilide. Experiment 9. Acetaminophen. Essay: Identification of Drugs. Experiment 10. TLC Analysis of Analgesic Drugs. Essay: Caffeine. Experiment 11. Isolation of Caffeine. Experiment 11A. Isolation of Caffeine from Tea Leaves. Experiment 11B. Isolation of Caffeine from a Tea Bag. Essay: Esters—Flavors and Fragrances. Experiment 12. Isopentyl Acetate (Banana Oil). Experiment 13. Methyl Salicylate (Oil of Wintergreen). Essay: Terpenes and Phenylpropanoids. Experiment 14. Isolation of Eugenol from Cloves. Essay: Stereochemical Theory of Odor. Experiment 15. Spearmint and Caraway Oil: (+)- and (-)- Carvones. Essay: The Chemistry of Vision. Experiment 16. Isolation of Chlorophyll and Carotenoid Pigments from Spinach. Essay: Ethanol and Fermentation Chemistry. Experiment 17. Ethanol from Sucrose. Part II: INTRODUCTION TO MOLECULAR MODELING. Essay: Molecular Modeling and Molecular Mechanics. Experiment 18. An Introduction to Molecular Modeling. Experiment 18A. The Conformations of n-Butane: Local Minima. Experiment 18B. Cyclohexane Chair and Boat Conformations. Experiment 18C. Substituted Cyclohexane Rings. Experiment 18D. cis- and trans-2-Butene. Essay: Computational Chemistry—Ab initio and Semiempirical Methods. Experiment 19. Computational Chemistry. Experiment 19A. Heats of Formation: Isomerism, Tautomerism, and Regioselectivity. Experiment 19B. Heats of Reactions: SN1 Reaction Rates. Experiment 19C. Density-Electrostatic Potential. Maps— Acidities of Carboxylic Acids. Experiment 19D. Density— Electrostatic Potential Maps: Carbocations. Experiment 19E. Density—LUMO Maps: Reactivities of Carbonyl Groups. Part III: PROPERTIES AND REACTIONS OF ORGANIC COMPOUNDS. Experiment 20. Reactivities of Some Alkyl Halides. Experiment 21. Nucleophilic Substitution Reactions: Competing Nucleophiles. Experiment 21A. Competing Nucleophiles with 1-Butanol or 2-Butanol. Experiment 21B. Competing Nucleophiles with 2-Methyl-2-Propanol. Experiment 21C. Analysis. Experiment 22. Hydrolysis of Some Alkyl Chlorides Experiment 23. Synthesis of n-Butyl Bromide and t-Pentyl Chloride. Experiment 23A. n-Butyl Bromide. Experiment 23B. t-Pentyl Chloride. Experiment 24. 4-Methylcyclohexene. Experiment 25. Phase-Transfer Catalysis: Addition of Dichlorocarbene to Cyclohexene. Essay: Fats and Oils. Experiment 26. Methyl Stearate from Methyl Oleate. Essay: Soaps and Detergents. Experiment 27. Preparation of Soap. Experiment 28. Preparation of a Detergent. Essay: Petroleum and Fossil Fuels. Experiment 29. Gas Chromatographic Analysis of Gasolines. Essay: Detection of Alcohol: The Breathalyzer. Experiment 30. Chromic Acid Oxidation of Alcohols Experiment 30A. Chromic Acid Oxidation of Alcohols—Visible Spectrophotometer Method. Experiment 30B. Chromic Acid Oxidation of Alcohols—UV-VIS Spectrophotometer Method. Essay: Green Chemistry. Experiment 31. Chiral Reduction of Ethyl Acetoacetate; Optical Purity Determination. Experiment 31A. Chiral Reduction of Ethyl Acetoacetate. Experiment

31B. NMR Determination of the Optical Purity of (S)-Ethyl 3-Hydroxybutanoate. Experiment 32. Nitration of Aromatic Compounds Using a Recyclable Catalyst. Experiment 33. An Oxidation-Reduction Scheme: Borneol, Camphor, Isoborneol. Experiment 34. Multi-Step Reaction Sequences: The Conversion of Benzaldehyde to Benzilic Acid. Experiment 34A. Preparation of Benzoin by Thiamine Catalysis Experiment 34B. Preparation of Benzil. Experiment 34C. Preparation of Benzilic Acid. Experiment 35. Tetraphenylcyclopentadienone. Experiment 36. Triphenylmethanol and Benzoic Acid. Experiment 36A. Triphenylmethanol. Experiment 36B. Benzoic Acid. Experiment 37. Resolution of (+/-)-alpha-Phenylethylamine and Determination of Optical Purity. Experiment 37A. Resolution of (+/-)-alpha-Phenylethylamine. Experiment 37B. Determination of Optical Purity Using NMR and a Chiral Resolving Agent. Experiment 38. The Aldol Condensation Reaction: Preparation of Benzalacetophenones Chalcones). Experiment 39. Preparation of an alpha,beta-Unsaturated Ketone via Michael and Aldol Condensation Reactions. Experiment 40. Enamine Reactions: 2-Acetylcyclohexanone. Experiment 41. 1,4-Diphenyl-1,3-Butadiene. Experiment 42. Relative Reactivities of Several Aromatic Compounds. Experiment 43. Nitration of Methyl Benzoate. Essay: Local Anesthetics. Experiment 44. Benzocaine. Essay: Pheromones: Insect Attractants and Repellents. Experiment 45. N,N-Diethylm-Toluamide: The Insect Repellent “OFF”. Essay: Sulfa Drugs. Experiment 46. Sulfa Drugs: Preparation of Sulfanilamide. Essay: Food Colors. Experiment 47. Chromatography of Some Dye Mixtures. Essay: Polymers and Plastics. Experiment 48. Preparation and Properties of Polymers: Polyester, Nylon, and Polystyrene. Experiment 48A. Polyesters. Experiment 48B. Polyamide (Nylon). Experiment 48C. Polystyrene. Experiment 48D. Infrared Spectra of Polymer Samples. Essay: Diels-Alder Reactions and Insecticides. Experiment 49. The Diels-Alder Reaction of Cyclopentadiene with Maleic Anhydride. Experiment 50. Photoreduction of Benzophenone and Rearrangement of Benzpinacol to Benzopinacolone. Experiment 50A. Photoreduction of Benzophenone. Experiment 50B. Synthesis of beta-Benzopinacolone: The Acid-Catalyzed Rearrangement of Benzpinacol. Essay: Fireflies and Photochemistry. Experiment 51. Luminol. Essay: The Chemistry of Sweeteners. Experiment 52. Carbohydrates. Experiment 53. Analysis of a Diet Soft Drink by HPLC. Essay: Chemistry of Milk. Experiment 54. Isolation of Casein and Lactose from Milk. Experiment 54A. Isolation of Casein from Milk. Experiment 54B. Isolation of Lactose from Milk. Part IV: IDENTIFICATION OF ORGANIC SUBSTANCES. Experiment 55. Identification of Unknowns. Experiment 55A. Solubility Tests. Experiment 55B. Tests for the Elements (N, S, X). Experiment 55C. Tests for Unsaturation. Experiment 55D. Aldehydes and Ketones. Experiment 55E. Carboxylic Acids. Experiment 55F. Phenols. Experiment 55G. Amines. Experiment 55H. Alcohols. Experiment 55I. Esters. Part V: PROJECTBASED EXPERIMENTS. Experiment 56. Preparation of a C-4






NEW!

Theory and Practice in the Organic Laboratory with Microscale and Standard Scale Experiments, 5e John A. Landgrebe - University of Kansas 608 pages | Casebound | 8 x 10 | ©2005 | 0-534-49627-X

Integrating 56 microscale and standard scale procedures and experiments, this comprehensive organic laboratory text allows all programs—even those that cannot afford a large investment in commercial kits—to complete effective microscale experiments. The Fifth Edition now features Discovery, CooperativeDiscovery, and Combination labs. Background chapters guide students through laboratory techniques, enabling them to work as real world chemists. This lab manual covers treatment of safety and hazardous waste disposal; coverage of laboratory techniques for the handling, synthesis, separation, and purification of organic compounds; and inclusion of spectroscopic methods for the identification of compounds.

NEW TO THIS EDITION In addition to the revised microscale and standard scale labs, the new edition features Discovery and CooperativeDiscovery labs, the latter involving students working together in teams to reach a conclusion that is then shared with the entire class. The Fifth Edition features eight new experiments: “Experiment 3: Thin-Layer Chromatography of Analgesics,” “Experiment 8: Solubility Properties of Covalent Molecules and Their Ionic Salts,” “Experiment 11: Raoult’s Law; Gas Chromatography,” “Experiment 25: The Diels-Alder Reaction of Maleic Anhydride and 1,3-Diphenylisobenzofuran,” “Experiment 28: Catalytic Hydrogenation,” “Experiment 38: Borohydride Reduction of 9-fluorenone,” “Experiment 42: Acetylsalicylic Acid; Preparation of Aspirin,” and “Experiment 49: Hexaphenylbenzene; Aldol and Diels-Alder Reactions.” Many other experiments have been revised significantly. The following labs have been introduced or revised to include a Discovery section or a Cooperative Discovery section for students to work together to reach results: “Experiment 11: Raoult’s Law; Gas Chromatography,” “Experiment 12: Fractional Distillation; Gas Chromatography,” “ Experiment 13: Free Radical


or C-5 Acetate Ester. Experiment 57. A Separation and Purification Scheme. Experiment 57A. Extractions with a separatory funnel. Experiment 57B. Extractions with a Screw-Cap centrifuge tube. Experiment 58. Isolation of Essential Oils from Allspice, Cloves, Cumin, Caraway, Cinnamon, or Fennel. Experiment 58A. Isolation of Essential Oils by Steam Distillation. Experiment 58B. Identification of the Constituents of Essential Oils by Gas Chromatography-Mass Spectrometry. Experiment 58C. Investigation of the Essential Oils of Herbs and Spices-Mini-Research Project. Experiment 59. Friedel-Crafts Acylation. Experiment 60. The Analysis of Antihistamine Drugs by Gas Chromatography-Mass Spectrometry. Experiment 61. Carbonation of an Unknown Aromatic Halide. Experiment 62. The Aldehyde Enigma. Experiment 63. Synthesis of Substituted Chalcones: A Guided-Inquiry Experience. Experiment 64. Michael and Aldol Condensation Reactions. Experiment 65. Esterification Reactions of Vanillin: The Use of NMR to Solve a Structure Proof Problem. Experiment 66. An Oxidation Puzzle. Part VI: THE TECHNIQUES. Technique 1. Laboratory Safety. Technique 2. The Laboratory Notebook, Calculations, and Laboratory Records. Technique 3. Laboratory Glassware: Care and Cleaning. Technique 4. How to Find Data for Compounds: Handbooks and Catalogues. Technique 5. Measurement of Volume and Weight. Technique 6. Heating and Cooling Methods. Technique 7. Reaction Methods. Technique 8. Filtration. Technique 9. Physical Constants of Solids: The Melting Point. Technique 10. Solubility. Technique 11. Crystallization: Purification of Solids. Technique 12. Extractions, Separations, and Drying Agents. Technique 13. Physical Constants of Liquids: The Boiling Point and Density. Technique 14. Simple Distillation. Technique 15. Fractional Distillation, Azeotropes. Technique 16. Vacuum Distillation, Manometers. Technique 17. Sublimation. Technique 18. Steam Distillation. Technique 19. Column Chromatography. Technique 20. Thin-Layer Chromatography. Technique 21. High-Performance Liquid Chromatography (HPLC). Technique 22. Gas Chromatography. Technique 23. Polarimetry. Technique 24. Refractometry. Technique 25. Infrared Spectroscopy. Technique 26. Nuclear Magnetic Resonance Spectroscopy (Proton NMR). Technique 27. Carbon13 Nuclear Magnetic Resonance Spectroscopy. Technique 28. Mass Spectrometry. Technique 29. Guide to the Chemical Literature. Appendix 1: Tables of Unknowns and Derivatives. Appendix 2: Procedure for Preparing Derivatives. Appendix 3: Index of Spectra.

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Halogenation; Relative Reactivity by Product Analysis,” “Experiment 19: Introduction to Infrared Spectroscopy,” “Experiment 24: Rates of Conversion of Alcohols to Alkyl Bromides,” “Experiment 28: Catalytic Hydrogenation,” “Experiment 31: Introduction to Nuclear Magnetic Resonance Spectroscopy,” and “Experiment 56: Spectroscopic Identification of an Unknown.” The new edition features 300 MHz spectra and a brief explanation with examples of two-dimensional Nuclear Magnetic Resonance spectra in the chapter on nuclear magnetic resonance spectroscopy.

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KEY FEATURES The text suggests how to keep a scientific notebook, discusses units, and explains additional sources of information on the properties of organic compounds. The text features comprehensive background chapters on many of the important techniques used by organic chemists including methods of separation, purification, and identification of organic compounds. Experiments can be done with a minimum of expensive glassware or specialized equipment and focus on the use of electrically heated sand baths as the primary heat source. For example, microscale extractions can be accomplished with inexpensive vials with a Teflon-lined cap. Experiments illustrate and introduce important laboratory procedures before applying them to the synthesis of new compounds. Spectroscopic methods are emphasized for the identification of the structures of compounds. This fifth edition contains both microscale and standard experiments in order to illustrate how techniques differ for isolating and purifying varying amounts of compounds. Both the background chapters and the experiments contain exercises appropriately placed to help students understand and master the material, as well as some advanced (optional) material to provide suitable background for students who are doing research that goes beyond the one-year laboratory course. Numerous equipment and apparatus figures have been added and repeated throughout the experiments to improve clarity and to save students time during the laboratory.

TA B L E O F C O N T E N T S Part I: TOOLS FOR THE ORGANIC LABORATORY. 1. Emergency Procedures and Safe Laboratory Practices. 2. General Laboratory Procedures. 3. Examination of Pure Compounds. 4. Chromatography. 5. Crystallization and Filtration. 6. Extraction and Drying. 7. Distillation and Related Techniques. 8. Introduction to Spectroscopy; Organic Structure Determination. 9. Nuclear Magnetic Resonance Spectroscopy. 10. Infrared Spectroscopy. 11. Mass Spectrometry. 12. Ultraviolet Visible Spectroscopy. 13. Special Laboratory

Procedures. 14. The Organic Chemical Literature. Part II: EXPERIMENTS. 1. Introduction to Organic Microtechniques. 2. Determination of Melting Point. 3. Thin-Layer Chromatography of Analgesics. 4. Column Chromatography. 5. High Performance Liquid Chromatography; Natural Products from Spices. 6. Natural Products by Extraction; Trimyristin and Cholesterol. 7. Caffeine; Isolation of an Alkaloid. 8. Solubility Properties of Covalent Molecules and Their Ionic Salts. 9. Extraction and Crystallization; Acid-Base Properties. 10. Extraction and Crystallization; Acid-Base Properties. 11. Raoult’s Law; Gas Chromatography. 12. Fractional Distillation; Gas Chromatography. 13. Free Radical Halogenation; Relative Reactivity by Product Analysis. 14. 2-Chloro-2-methylbutane (tert-Amyl Chloride). 15. Kinetic Investigation of Unimolecular Solvolysis. 16. Methylcyclohexenes; Alcohol Dehydration. 17. Resolution of a Racemic Modification. 18. Diphenylacetylene from Stilbene. 19. Introduction to Infrared Spectroscopy. 20. Divalent Carbon Intermediates; Phase Transfer Catalysis. 21. Homophthalic Acid; Oxidative Cleavage of a Double Bond. 22. Triphenylcarbinol; Addition of a Grignard Reagent to a Ketone. 23. Benzoic Acid; Carbonation of a Grignard Reagent. 24. Rates of Conversion of Alcohols to Alkyl Bromides. 25. The Diels-Alder Reaction of Maleic Anhydride and 1,3Diphenylisobenzofuran. 26. Oxidation of (-)-Borneol to (-)Camphor; Specific Rotation. 27. Oxidation of Alcohols to Aldehydes and Ketones. 28. Catalytic Hydrogenation. 29. Kinetic and Thermodynamic Reaction Conditions. 30. Heat of Reaction; Measurement of Resonance Energy. 31. Introduction to Nuclear Magnetic Resonance Spectroscopy. 32. Acetanilide to p Nitroaniline. 33. Aminoacetophenone; Selective Reduction of Nitro. 34. 4-Methylbenzophenone; Friedel-Crafts Acylation. 35. Photoreduction of Aromatic Ketones. 36. Carbocation Rearrangements; Benzopinacolone. 37. Aryl Migratory Aptitudes in Carbocation Rearrangements. 38. Borohydride Reduction of 9-fluorenone. 39. HydroborationOxidation of 1-Hexene. 40. Synthetic Organic Polymers. 41. Electronic Effects of Substituents in Reactions; Acidity Constant Determination. 42. Acetylsalicylic Acid; Preparation of Aspirin. 43. Fischer Esterification. 44. Capryl Chloride and Capramide. 45. Chemiluminescence. 46. Synthesis of Sulfa Drugs; Using a Protected Amino Group. 47. Benzyl Alcohol; Complex Metal Hydride Reductions. 48. 9-Benzal- and 9Benzylfluorene; Aldol and Cannizzaro Type Reactions. 49. Hexaphenylbenzene; Aldol and Diels-Alder Reactions. 50. Conjugate (Michael) Addition to , -Unsaturated Carbonyl. 51. Synthetic Dyes. 52. Forensic Chemistry; Detecting Traces of Blood. 53. Phenanthridone; Beckmann Rearrangement to a Heterocycle. 54. Qualitative Organic Analysis; Classification Tests. 55. Chemical and Spectral Analysis; Unknown Identification. 56. Spectroscopic Identification of an Unknown. Appendix. Answers to Selected Chapter Exercises. Index.



Online Instructor’s Manual


Green Organic Chemistry: Strategies, Tools, and Laboratory Experiments Kenneth Doxsee and James Hutchison — both of University of Oregon


Developing the green organic program at the University of Oregon, Kenneth Doxsee and James Hutchison saw the urgent need and rapidly growing demand for green chemistry laboratory materials. This lab text describes the tools and strategies of green chemistry, and the lab experiments that allow investigation of organic chemistry concepts and techniques in a greener laboratory setting. Green Organic Chemistry: Strategies, Tools and Laboratory Experiments was developed and successfully tested as a direct replacement for the traditional organic chemistry laboratory curriculum. Thus, the conceptual themes and experimental techniques important to the modern practice of organic chemistry can be taught in the context of more environmentally-benign laboratory experiments. Students acquire the tools to assess the health and environmental impacts of chemical processes and the strategies to improve develop new processes that are less harmful to human health and the environment. The curriculum introduces a number of state-of-the-art experiments and reduces reliance on expensive environmental controls, such as fume hoods.

KEY FEATURES The text includes nineteen extensively student-tested laboratory experiments that teach fundamental organic chemistry concepts and lab skills in a more environmentally-friendly (greener) fashion. Concrete comparisons between traditional approaches and greener approaches provide students with experience identifying health and environmental hazards and developing alternative, greener procedures. The text features ten comprehensive introductory chapters describing the strategies and tools used in practicing greener chemistry. These chapters provide a context for the laborato-


ry experiments and introduce the key concepts and strategies to students and instructors alike. The authors teach practical skills such as hazard identification and minimization, and economic analysis in addition to fundamental concepts. Experimental procedures were not written with reference to any particular text thus allowing use with any organic chemistry laboratory techniques text. Green chemical methods achieve hazard reduction at all reaction scales, permitting the introduction of larger-scale experimentation, using standard laboratory glassware, while reducing reliance on fume hoods. This laboratory manual provides a unique context for more detailed discussions of chemical hazards and the effects of chemicals on human health and the environment. The use of a set of green chemistry principles throughout the text is emphasized and includes: the minimization or elimination of hazardous solvents whenever possible, the identification and use the most benign reagents possible, and the development and use efficient reaction chemistry. Procedures are provided that are readily employed using either miniscale or microscale glassware.

TA B L E O F C O N T E N T S Graphical Abstracts for the Experiments. 1. Introduction. 2. Identification and Evaluation of Chemical Hazards. 3. Chemical Exposure and Environmental Contamination. 4. Sources of Information About Chemical Hazards. 5. Introduction to Green Chemistry. 6. Alternative Solvents 7. Alternative Reagents. 8. Reaction Design and Efficiency. 9. Alternative Feedstocks and Products. 10. The Big Picture and Green Chemistry Metrics Laboratory Experiments. 11. Preface To The Experimental Section Experiments. 1: Solventless Reactions: The Aldol Reaction. 2: Bromination of An Alkene: Preparation of Stilbene Dibromide. 3: A Greener Bromination of Stilbene. 4: Preparation and Distillation of Cyclohexene. 5: Synthesis and Recrystallization of Adipic Acid. 6: Oxidative Coupling of Alkynes: The Glaser-Eglinton-Hay Coupling. 7: Gas-Phase Synthesis, Column Chromatography and Visible Spectroscopy of 5,10,15,20-Tetraphenylporphyrin. 8: Microwave Synthesis of 5,10,15,20-Tetraphenylporphyrin. 9: Metallation of 5,10,15,20-Tetraphenylporphyrin. 10: Measuring Solvent Effects: Kinetics of Hydrolysis of tert-Butyl Chloride. 11: Molecular Mechanics Modeling. 12: Electrophilic Aromatic Iodination. 13: Palladium-Catalyzed Alkyne Coupling/Intramolecular Alkyne Addition: Natural Product Synthesis. 14: Resin-Based Oxidation Chemistry. 15: Carbonyl Chemistry: Thiamine-Mediated Benzoin Condensation of Furfural. 16: Solid-Phase Photochemistry. 17: Applications of Organic Chemistry: Patterning Surfaces With Molecular Films. 18: The Friedel-Crafts Reaction: Acetylation of Ferrocene. 19: Combinatorial Chemistry: Antibiotic Drug Discovery. Appendix A: The Twelve Principles of Green Chemistry.


ANCILLARIES

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BROOKS/COLE LABORATORY SERIES Organic Chemistry ANCILLARIES



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Experimental Organic Chemistry: A Miniscale and Microscale Approach, 3e John C. Gilbert and Stephen F. Martin — both of University of Texas, Austin 896 pages | Casebound | ©2002 | 0-03-034063-2

This proven and well-tested laboratory manual for organic chemistry students contains procedures for both miniscale (also known as small scale) and microscale users. This lab manual gives students all the necessary background to enter the laboratory with the knowledge to perform the experiments with confidence. For the microscale labs, experiments were chosen to provide tangible quantities of material, which can then be analyzed. Chapters 1-2 introduce students to the equipment, record keeping, and safety of the laboratory. Chapters 3-6, and 8 are designed to introduce students to laboratory techniques needed to perform all experiments. In Chapters 7 and 9 through 20, students are required to use the techniques to synthesize compounds and analyze their properties. In Chapter 21, students are introduced to multi-step syntheses of organic compounds, a practice well known in chemical industry. In Chapter 23, students are asked to solve structures of unknown compounds. Chapter 24 introduces students to reading the literature in organic chemistry.

Historical Highlights are brief essays designed to familiarize students with the lives of chemical pioneers who have advanced the field of chemistry. Accurately drawn art shows students how to set up an experiment with confidence. Margin drawings of equipment remind students about the set up for such techniques as distillation and reflux. Each experiment begins with a thorough discussion of the theory and procedures involved. Experimental procedures are laid out in a clear format. Chapter exercises help students to test their knowledge of the material.

TA B L E O F C O N T E N T S 1. Introduction, Record Keeping, and Laboratory Safety. 2. Techniques and Apparatus. 3. Solids: Recrystallization and Melting Points. 4. Liquids. 5. Extraction. 6. Chromatography. 7. Stereoisomers. 8. Spectral Methods. 9. Alkanes. 10. Alkenes. 11. Alkynes. 12. Dienes: The Diels-Alder Reaction. 13. Kinetic and Thermodynamic Control of a Reaction. 14. Nucleophilic Aliphatic Substitution: Preparation for Alkyl Halides. 15. Electrophilic Aromatic Substitution. 16. Oxidation of Alcohols and Carbonyl Compounds. 17. Reduction Reactions of Double Bonds: Alkenes, Carbonyl Compounds, and Imines. 18. Reactions of Carbonyl Compounds. 19. Organometallic Chemistry. 20. Carboxylic Acids and Their Derivatives. 21. Polymers. 22. Carbohydrates. 23. Identifying Organic Compounds. 24. The Literature of Organic Chemistry.


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KEY FEATURES A Spectroscopy CD-ROM is packaged free with each text. The CD-ROM contains pre-lab exercises for preparing for a new experiment, proton NMR spectra for analyzing chemical shifts, integration, and coupling constants, IR spectra for analyzing functional groups, MSDS (material safety data sheets) tables for checking the safe handling of the materials in each experiment, and derivative tables. Marginal icons show the NMR and IR spectra located in the text as well as on the CD-ROM. Emphasis on safety. Safety Alerts and Wrapping It Up sections alert students to possible hazards and proper disposal of spent chemicals.



Donald L. Pavia, Gary M. Lampman, George S. Kriz — all of Western Washington University; and Randall G. Engel — Edmonds Community College 375 pages | Casebound | ©2002 | 0-03-034311-9

The well-known and tested organic chemistry laboratory techniques of the two best-selling organic chemistry lab manuals: Introduction to Organic Laboratory Techniques: A Small Scale Approach and Introduction to Organic Laboratory Techniques: A Microscale Approach, Third Edition are now assembled in one textbook. Professors can use any experiments alongside Microscale and Macroscale Techniques in the Organic Laboratory. Experiments can be selected and assembled from the two Pavia organic chemistry lab manuals, from professors’ homegrown labs, or even competing texts. The 375 page, hardcover book serves as a reference for all students of organic chemistry. With clearly written prose and accurately drawn diagrams, students can feel confident setting up and running organic labs.

KEY FEATURES Caution boxes emphasize careful handling of chemicals and the importance of safety in the laboratory. Side-by-side discussions of microscale and macroscale techniques provide a quick reference and point of comparison. Clear and accurate diagrams of laboratory set-ups increase students’ confidence in setting up a lab. End-of-chapter problems test students’ mastery of the material. The laboratory techniques featured in the book have been tested and used by thousands of students.

TA B L E O F C O N T E N T S 1. Laboratory Safety. 2. Advance Preparation and Laboratory Records. 3. Laboratory Glassware. 4. How to Find Data for Your Compound: Handbooks and Catalogues. 5. Measurement of Volume and Weight. 6. Heating and Cooling Methods. 7. Reaction Methods. 8. Filtration. 9. Physical Constants of Solids: The Melting Point. 10. Solubility. 11. Crystallization: Purification of Solids. 12. Extractions, Separations, and Drying Agents. 13. Physical Constants of Liquids: Boiling Point and Density. 14. Simple Distillation. 15. Fractional Distillation; Azeotropes. 16. Vacuum Distillation; Manometers.


ANCILLARIES Student Lab Research Notebook Long Version, Top-bound Short Version, Top-bound

0-03-027288-2 0-03-027289-0

Organic Chemistry Laboratory: Standard and Microscale Experiments, 3e Charles E. Bell — Old Dominion University; Douglas Taber — University of Delaware; and Allen K. Clark — Old Dominion University 700 pages | Casebound | ©2001 | 0-03-029272-7

Intended for the two-term organic chemistry laboratory course. The new edition continues to offer a wide variety of organic lab experiments for both standard and microscale formats and features unusually strong coverage of spectroscopy.

KEY FEATURES Features all modern spectroscopy techniques and includes additional spectroscopy problems. The introduction to magnetic resonance spectroscopy is designed to enhance student understanding and to facilitate use. As in previous editions, readability continues to be one of the hallmark features of the text. Each experiment can be carried out in one or two 3-hour lab periods. Experiments are practical and work as written. Step-by-step approach to spectroscopy facilitates student learning of this difficult material.


Microscale and Macroscale Techniques in the Organic Laboratory

17. Sublimation. 18. Steam Distillation. 19. Column Chromatography. 20. Thin-Layer Chromatography. 21. HighPerformance Liquid Chromatography (HPLC). 22. Gas Chromatography. 23. Polarimetry. 24. Refractometry. 25. Infrared Spectroscopy. 26. Nuclear Magnetic Resonance Spectroscopy (Proton NMR). 27. Carbon-13 Nuclear Magnetic Resonance Spectroscopy. 28. Mass Spectrometry. 29. Computational Chemistry. 30. Guide to the Chemical Literature.

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TA B L E O F C O N T E N T S

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1. Introduction. 2. Melting Points. 3. Recrystallization. 4. Extraction. 5. Distillation. 6. Gas Chromatography. 7. Column Chromatography. 8. Thin Layer Chromatography. 9. High Performance Liquid Chromatography. 10. Steam Distillation of Essential Oils. 11. Infrared Absorption Spectroscopy. 12. Spectroscopic Structure Determination: A Lifelong Quest. 13. Proton Nuclear Magnetic Resonance. 14. Advanced Structure Determination. 15. The Literature of Organic Chemistry. 16. Properties of Hydrocarbons. 17. Nucleophylic Substitution of Alkyl Halides. 18. Properties of Alcohols. 19. The Grignard Reaction. 20. Dehydration of Alcohols. 21. Oxidation and Reduction. 22. Aldehydes and Ketones. 23. Determination of pK(a): Effects of Substituents on Acidity. 24. Carboxylic Acid Mini-unknown. 25. Esterification and Saponification: Effect of Substituents on Reactivity. 26. Friedel-Crafts Alkylation and Acylation. 27. Aromatic Nitration. 28. Aromatic Nucleophilic Substitution. 29. Properties of Amines. 30. Chemiluminescence. 31. Photodimerization of Benzophenone. 32. The Diels-Alder Reaction. 33. Phase Transfer Catalysis. 34. Derivatives of Caroboxylic Acids: Synthesis of a Plant Hormone. 35. Synthesis of Coumarin. 36. Benzyne. 37. Heterocyclic Syntheses: Pyrimidines, Pyridones, Isoxazoles, Quinolines, and Indoles. 38. Heterocyclic Synthesis: Phenytoin. 39. Synthesis of Sulfanilamide. 40. Resolution of a-Phenylethylamine. 41. Chemistry of Sugars. 42. Acid-Catalyzed and EnzymeCatalyzed Hydrolosis of Polysaccharides. 43. Analysis of Fats and Oils. 44. Synthetic Organic Polymers. 45. Dyes and Dyeing. 46. Qualitative Organic Analysis. Appendices. A. Selected Atomic Weights. B. Common Acids and Bases. C. Common Organic Liquids. D. Representative Calculations.


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Organic Laboratory Techniques, 3e Ralph J. Fessenden and the late Joan S. Fessenden — both of the University of Montana and Patty J. Feist, University of Colorado

256 pages | Paperbound | 7-3/8 x 9-1/4 | ©2001 | 0-534-37981-8

This highly effective and practical manual can be used as a supplementary text for the organic chemistry laboratory course— and with virtually any main text—in which experiments are supplied by the instructor, or where students work independently. Each technique contains a brief theoretical discussion and the steps used in each technique, along with common problems that might arise. These respected and renowned authors include supplemental or related procedures, suggested experiments, and suggested readings for many of the techniques. Additionally, each chapter ends with a set of study problems that focus on the practical aspects of each technique, and, Microscale procedures are included throughout the text, as appropriate. Additional exercises, reference material, and quizzes are available online.

KEY FEATURES Coverage of spectroscopy, a technique used to determine the structure of molecules, a critical skill for organic chemistry students to develop is included. Microscale procedures are included with each technique, as appropriate. The Chemical Literature section contains material on searching the Internet and other computer resources for related information. Techniques include information on computer interface of new instruments. Suggested readings and appropriate links are included on the Brooks/Cole Chemistry Resource Center. See Webworks at www.brookscole.com/chemistry. Each text allows your student access to text-specific Internet resources. This includes exercises, a library of over 400 compounds complete with links to useful databases (NIST, NTP, MSDS, and IRIS) and two supplemental modules on spectroscopy with 100 compounds for analysis. Spectroscopy problems are presented in tutorial format. Discussions on sampling techniques for spectroscopy (IR, NMR, UV/Visible) are included. The hallmark feature of emphasis on safety appears throughout this edition. Emphasis is placed on chemical container labels and on Material Safety Data Sheets (MSDS).



TA B L E O F C O N T E N T S Introduction to the Organic Laboratory / Safety in the Laboratory / The Laboratory Notebook / Laboratory Equipment. 1. Crystallization. 2. Melting Points. 3. Extraction. 4. Drying Organic Solutions. 5. Simple Distillation. 6. Fractional Distillation. 7. Vacuum Distillation. 8. Steam Distillation. 9. Sublimation. 10. Refractive Index. 11. Column Chromatography. 12. Thin Layer Chromatography. 13. Gas Chromatography. 14. Carrying Out Typical Reactions. 15. Infrared Spectroscopy. 16. Proton Nuclear Magnetic Resonance Spectroscopy. 17. The Chemical Literature. Appendices. I. Commonly Used Calculations. Molarity / Normality / Dilutions / Percent Concentrations / Percent Yields and Theoretical Yields. II. Elemental Analyses. Determining the Empirical Formula / Determining the Molecular Formula / Interpreting the Results of Elemental Analysis / Degree of Unsaturation. III. Health Hazards of Compounds Used In Organic Chemistry. Where to Find Chemical Hazard Information / Understanding Health Hazard Warnings.

ANCILLARIES Instructor’s Manual http://chemistry.brookscole.com Student Lab Research Notebook Long Version, Top-bound 0-03-027288-2 Short Version, Top-bound 0-03-027289-0

Introduction to Spectroscopy, 3e Donald L. Pavia, Gary M. Lampman, and George S. Kriz — all of Western Washington University 515 pages | Paperbound | ©2001 | 0-03-031961-7

A true introductory text for learning the spectroscopic techniques of Nuclear Magnetic Resonance, Infrared, Ultraviolet, and Mass Spectrometry. It can be used in a stand alone spectroscopy course or as a supplement to the sophomore-level organic chemistry course.

KEY FEATURES Features an abundance of new problems, including more challenging problems and problems that are not answered in the book, providing professors with questions for homework assignments or quizzes. Many high-resolution 300-MHz NMR spectra replace older 60-MHz spectra. A survey section on proton-NMR provides a qualitative treatment of spectra by functional group. A discussion of cross polarization in the C-13 NMR spectra section. How to Solve Mass Spectrometry Problems section. Each chapter includes examples and a large number of problems to provide students with sufficient practice to master the material. The chapter on Combined Structure Problems uses information gathered from previous chapters to test students’ knowledge of all the techniques of structure elucidation.

TA B L E O F C O N T E N T S 1. Molecular Formulas and What Can Be Learned from Them. 2. Infrared Spectroscopy. 3. Nuclear Magnetic Resonance Spectroscopy Part One: Basic Concepts. 4. Nuclear Magnetic Resonance Spectroscopy Part Two: Carbon-13 Spectra, Including Heteronuclear Coupling With Other Nuclei. 5. Nuclear Magnetic Resonance Spectroscopy Part Three: SpinSpin Coupling. 6. Nuclear Magnetic Resonance Spectroscopy Part Four: Other Topics in One-Dimensional NMR. 7. Ultraviolet Spectroscopy. 8. Mass Spectrometry. 9. Combined Structure Problems. 10. Nuclear Magnetic Resonance Spectroscopy Part Five: Advanced NMR Techniques. Answers to Selected Problems. Appendices. 1. Infrared Absorption Frequencies of Functional Groups. 2. Some Representative Chemical Shift Values for Various Types of Protons. 3. Typical Proton Coupling Constants. 4. Calculation of Proton (1H)



Basic Microscale procedures, such as material transfer, crystallization, distillation, and extraction are provided throughout the text.

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Chemical Shifts. 5. Calculation of Carbon-13 Chemical Shifts. 6. C-13 Coupling Constants. 7. Tables of Precise Masses and Isotopic Abundance Ratios for Molecular Ions Under Mass 100 Containing Carbon, Hydrogen, Nitrogen, and Oxygen. 8. Common Fragment Ions Under Mass 105. 9. Handy-Dandy Guide to Mass Spectral Fragmentation Patterns. 10. Index of Spectra. Index.

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Introduction to Organic Laboratory Techniques: A Microscale Approach, 3e Donald l. Pavia, Gary M. Lampman, George S. Kriz, all of Western Washington University; and Randall G. Engel, Edmonds Community College 915 pages | Casebound | ©1999 | 0-03-026561-4

This edition features the successful format that has characterized the previous editions. It includes essays that add relevance and interest to the experiments, and emphasis on the development of the important laboratory techniques, the use of spectroscopy and instrumental methods of analysis, a section featuring conventional-scale experiments and methods, and a wide selection of well-tested and well-written experiments.

TA B L E O F C O N T E N T S Introduction / Welcome / Laboratory Safety / Advance Preparation and Laboratory Records / Laboratory Glassware. PART ONE: BASIC LABORATORY CONCEPTS. 1. Introduction to Microscale Laboratory. 2. Solubility. 3. Crystallization. 4. Extraction. 5. Chromatography. 6. Simple and Fractional Distillation. A. Simple and Fractional Distillation (Semi-Microscale Procedure). B. Simple and Fractional Distillation (Microscale Procedure). PART TWO: INTRODUCTION TO MICROSCALE METHODS. 7. Isolation of the Active Ingredient in an Analgesic Drug. Essay: Aspirin. 8. Acetylsalicylic Acid. Essay: Analgesics. 9. Acetaminophen. A. Acetaminophen (Microscale Procedure). B. Acetaminophen (Semi-Microscale Procedure). Essay: Identification of Drugs. 10. TLC Analysis of Analgesic Drugs. Essay: Caffeine. 11. Isolation of Caffeine from Tea. Essay: Esters—Flavors and Fragrances. 12. Isopentyl Acetate (Banana Oil). A. Isopentyl Acetate (Microscale Procedure). B. Isopentyl Acetate (SemiMicroscale Procedure). Essay: Terpenes and Phenylpropanoids.

13. Essential Oils from Spices: Oil of Cloves. A. Oil of Cloves (Microscale Procedure). B. Oil of Cloves (Semi-Microscale Procedure). Essay: Stereochemical Theory of Odor. 14. Spearmint and Caraway Oil: (+)-and (-)-Carvones. Essay: The Chemistry of Vision. 15. Isolation of Chlorophyll and Carotenoid Pigments from Spinach. PART THREE: INTRODUCTION TO MOLECULAR MODELING. Essay: Molecular Modeling and Molecular Mechanics. 16. An Introduction to Molecular Modeling. A. The Conformations of n-Butane: Local Minima. B. Cyclohexane Chair and Boat Conformations. C. Substituted Cyclohexane Rings. D. cis- and trans-2-Butene. Essay: Computational Chemistry—Ab Initio and Semiempirical Methods. 17. Computational Chemistry. A. Heats of Formation: Isomerism, Tautomerism, and Regioselectivity. B. Heats of Reaction: SN1 Reaction Rates. C. Density-Electrostatic Potential Maps—Acidities of Carboxylic Acids. D. Density-Electrostatic Potential Maps: Carbocations. E. Density-LUMO Maps: Reactivities of Carbonyl Groups. PART FOUR: PREPARATIONS AND REACTIONS OF ORGANIC COMPOUNDS. 18. Reactivities of Some Alkyl Halides. 19. Nucleophilic Substitution Reactions: Competing Nucleophiles. A. Competitive Nucleophiles with 1-Butanol or 2-Butanol. B. Competitive Nucleophiles with 2-Methyl-2-propanol. C. Analysis. 20. Hydrolysis of Some Alkyl Chlorides. 21. Synthesis of n-Butyl Bromide and t-Pentyl Chloride. A. nButyl Bromide (Microscale Procedure). B. n-Butyl Bromide (Semi-Microscale Procedure). C. t-Pentyl Chloride (Microscale Procedure). D. t-Pentyl Chloride (Semi-Microscale Procedure). 22. Elimination Reactions: Dehydration and Dehydrohalogenation. A. Dehydration of 1-Butanol and 2Butanol. B. Dehydrobromination of 1-Bromobutane and 2Bromobutane. 23. 4-Methylcyclohexene. A. 4-Methylcyclohexene (Microscale Procedure). B. 4-Methylcyclohexene (SemiMicroscale Procedure). Essay: Petroleum and Fossil Fuels. 24. Gas-Chromatographic Analysis of Gasolines. Essay: Fats and Oils. 25. Methyl Stearate from Methyl Oleate. 26. PhaseTransfer Catalysis: Addition of Dichlorocarbene to Cyclohexene Essay: Ethanol and Fermentation Chemistry. 27. Ethanol from Sucrose. Essay: Detection of Alcohol: The Breathalyzer. 28. An Oxidation-Reduction Scheme: Borneol, Camphor, Isoborneol. 29. Chiral Reduction of Ethyl Acetoacetate: Optical Purity Determination Using Chiral Shift Reagent. A. Chiral Reduction of Ethyl Acetoacetate. B. NMR Determination of the Optical Purity of (S)-(+)-Ethyl 3-Hydroxybutanoate. 30. Resolution of (±)-a-Phenylethylamine and Determination of Optical Purity. A. Resolution of (±)-a-Phenylethylamine. B. Determination of Optical purity Using NMR and a Chiral Resolving Agent. 31. Triphenylmethanol and Benzoic Acid. A. Triphenylmethanol B. Benzoic Acid. Essay: Thiamine as a Coenzyme. 32. Coenzyme Synthesis of Benzoin. 33. Benzil. 34. Benzilic Acid. 35. The Aldol Condensation Reaction: Preparation of Benzalacetophenones (Chalcones). 36. Preparation of an a,b-Unsaturated Ketone via Michael and Aldol Condensation Reactions. 37. Enamine Reactions: 2-Acetylcyclohexanone. 38. 1,4-Diphenyl-1, 3-butadi-




Resonance Spectroscopy. 5. Carbon-13 Nuclear Magnetic Resonance Spectroscopy. 6. Mass Spectrometry. 7. Index of Spectra. Index.


0-03-023138-4 0-03-027288-2 0-03-027289-0


ene. 39. Relative Reactivities of Several Aromatic Compounds. 40. Nitration of Methyl Benzoate. Essay: Local Anesthetics. 41. Benzocaine. 42. Methyl Salicylate (Oil of Wintergreen). Essay: Soaps and Detergents. 43. Preparation of a Soap. 44. Preparation of a Detergent. Essay: Pheromones: Insect Attractants and Repellants. 45. N, N-Diethyl-m-toluamide: The Insect Repellent “OFF”. Essay: Sulfa Drugs. 46. Sulfa Drugs: Preparation of Sulfanilamide. Essay: Polymers and Plastics. 47. Preparation of Properties of Polymers: Polyester, Nylon, and Polystyrene. A. Polyesters. B. Polyamide (Nylon). C. Polystyrene. D. Infrared Spectra of Polymer Samples. Essay: Diels-Alder Reaction and Insecticides. 48. The Diels-Alder Reaction of Cyclopentadiene with Maleic Anhydride. 49. Photoreduction of Benzophenone and Rearrangement of Benzpinacol to Benzopinacolone. A. Photoreduction of Benzophenone. B. Synthesis of b-Benzopinacolone: The Acid-Catalyzed Rearrangement of Benzpinacol. Essay: Fireflies and Photochemistry. 50. Luminol. PART FIVE: IDENTIFICATION OF ORGANIC SUBSTANCES. 51. Identification of Unknowns. A. Solubility Tests. B. Tests of the Elements (N, S, X). C. Tests for Unsaturation. D. Aldehydes and Ketones. E. Carboxylic Acids. F. Phenols. G. Amines. H. Alcohols. I. Esters. PART SIX: MACROSCALE EXPERIMENTS. Essay: How to Scale Up a Reaction: Macroscale Methods. 52. Preparation of a C-4 or C-5 Acetate Ester. 53. Synthesis of n-Butyl Bromide and t-Pentyl Chloride. A. n-Butyl Bromide. B. t-Pentyl Chloride. 54. Nitration of Methyl Benzoate. PART SEVEN: PROJECTBASED EXPERIMENTS. 55. A Separation and Purification Scheme. Essay: How to Scale Down an Experiment. 56. Conversion of Cyclohexanol to Bromocyclohexane. 57. Isolation of Essential Oils from Allspice, Cloves, Cumin, Caraway, Cinnamon, or Fennel. A. Isolation of Essential Oils by Steam Distillation. B. Identification of the Constituents of Essential Oils by Gas Chromatography-Mass Spectrometry. C. Investigation of the Essential Oils of Herbs and Spices—A Mini-Research Project. 58. Friedel-Crafts Acylation. 59. The Analysis of Antihistamine Drugs by Gas Chromatography-Mass Spectrometry. 60. The Aldehyde Enigma. 61. Michael and Aldol Condensation Reactions. 62. Esterification Reactions of Vanillin: The Use of NMR to Solve a Structure Proof Problem. PART EIGHT: THE TECHNIQUES. 1. Measurement of Volume and Weight. 2. Heating and Cooling Methods. 3. Reaction Methods. 4. Filtration. 5. Crystallization: Purification of Solids. 6. Physical Constants: Melting Points, Boiling Points, Density. 7. Extractions, Separations, and Drying Agents. 8. Simple Distillation. 9. Vacuum Distillation, Manometers. 10. Fractional Distillation, Azeotropes. 11. Steam Distillation. 12. Column Chromatography. 13. High-Performance Liquid Chromatography (HPLC). 14. Thin-Layer Chromatography. 15. Gas Chromatography. 16. Sublimation. 17. Polarimetry. 18. Refractometry. 19. Preparation of Samples for Spectroscopy. 20. Guide to the Chemical Literature. APPENDICES. 1. Tables of Unknowns and Derivatives. 2. Procedures for Preparing Derivatives. 3. Infrared Spectroscopy. 4. Nuclear magnetic

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BROOKS/COLE LABORATORY SERIES Organic Chemistry: CER Course Suggestions



ORGANIC CHEMISTRY

34

TECHNIQUES

SYNTHESIS

TECH 700: Practicing Safety in the Organic Chemistry Laboratory TECH 701: Measuring the Melting Points of Compounds and Mixtures TECH 702: Using Microscale Techniques TECH 703: Purifying Acetanilide by Recrystallization TECH 704: Separating Cyclohexane and Toluene by Distillation TECH 705: Separating Acids and Neutral Compounds of Solvent Extraction TECH 706: Separating Camphor from Beta-Carotene by Sublimation TECH 707: Separating a Mixture by Thin-Layer Chromatography TECH 708: Separating Ferrocene and Acetylferrocene by Adsorption Column Chromatography TECH 709: Separating and Identifying Mixtures by Gas Chromatography TECH 710: Identifying an Unknown Compound by Infrared Spectroscopy TECH 711: Using NMR Spectroscopy to Identify an Unknown Organic Compound TECH 722: Isolating Clove Oil from Cloves Using Steam Distillation TECH 752: Resolving a Racemic Mixture: Using (-)-Proline to Separate (+- )-Phenylsuccinic Acid

SYNT 713: Preparing Isopentylacetate by the Fischer Esterification SYNT 717: The Diels-Alder Reaction of Anthracene with Maleic Anhydride SYNT 718: Nucleophilic Addition to Carbonyl: Grignard Reaction with an Aldehyde SYNT 719: Brominating Alkenes SYNT 720: The Aldol Condensation: Synthesis of Dibenzalacetone SYNT 721: Synthesis of Trans-9-(2-Phenylethenyl)Anthracene: A Wittig Reaction SYNT 723: Friedel-Crafts Acylation: Synthesis of 4-Methoxyacetophenone SYNT 724: Friedel-Crafts Alkylation: Kinetic versus Thermodynamic Control SYNT 725: Oxidizing Methoxybenzyl Alcohol to Methoxybenzaldehyde Using Phase-Transfer Catalysis SYNT 726: Two Methods for the Synthesis of Phenacetin SYNT 730: Dyes and Dyeing SYNT 731: Luminol Synthesis and Chemiluminescence SYNT 732: Isolating Caffeine from Tea SYNT 737: Thiamine-Catalyzed Benzoin Condensation SYNT 738: Copper-Catalyzed Oxidation of Benzoin to Benzil SYNT 739: The Synthesis of a Superabsorbent Polymer SYNT 740: Preparing Ethanol by Fermentation SYNT 743: Converting Benzaldehyde to Benzilic Acid: A Multistep Synthesis SYNT 745: Synthesizing Aspirin: The Acetylation of Salicylic Acid SYNT 746: Acetaminophen: The Acetylation of p-Aminophenol SYNT 748: Formation of Benzyne and Its Diels-Alder Reaction: A Multistep Reaction Sequence SYNT 754: A Multistep Synthesis Sequence: An Aldol Condensation, a Michael Addition, and Ethylene Ketal Formation

MISCELLANEOUS MISC 744: Naming Organic Compounds

REACTIONS REAC 712: Dehydrating Cyclohexanol REAC 714: Studying SN1 and SN2 Reactions: Nucleophilic Substitution REAC 715: Reducing Benzil Using Sodium Borohydride REAC 716: Nitrating Acetanilide or Methyl Benzoate: Electrophilic Aromatic Substitution REAC 734: Molecular Rearrangement Reactions: Azobenzene and Benzilic Acid REAC 736: The Pinacol Rearrangement REAC 741: Free Radical Chlorination REAC 742: Acid-Catalyzed Hydration of 1-Hexene to Make 2-Hexanol REAC 747: Hydroboration and Oxidation of 1-Hexene to Make 1-Hexanol REAC 749: Nucleophilic Aromatic Substitution REAC 750: Cannizzaro Reaction

KINETICS KINE 733: The Kinetics of Solvolysis of 2-Chloro-2-Methylpropane KINE 755: Synthesis and Kinetics of the Lophine Radical

ANALYSIS ANAL ANAL ANAL ANAL ANAL ANAL

727: Classifying an Unknown Compound by Functional Group 728: Identifying an Unknown Aldehyde or Ketone 729: Identifying an Unknown Alcohol 735: Catalytic Hydrogenation of Unknowns 751: Enantiomeric Purity of Commercial Ibuprofen 756: Determining the Alcohol Content of Beers and Wines


BROOKS/COLE LABORATORY SERIES Biochemistry

NEW FOR 2006!

Experiments in Biochemistry: A Hands-on Approach, 2e Shawn O. Farrell and Lynn E. Taylor — both of Colorado State University 336 pages | Casebound | 8-1/2 x 11 | ©2006 | 0-495-01317-X

“Essential Information” boxes highlight pertinent information. “References and Further Reading” sections are at the end of each chapter. An additional “Problem Set” appears in each chapter.

TA B L E O F C O N T E N T S Introduction to the Text. Objectives of the Biochemistry Laboratory. Chapter Format of Hands on Biochemistry. 1. Biochemistry Boot Camp. 2. Acids, Bases, and Buffers. 3. Spectrophotometry. 4. Enzyme Purification. 5. Ion Exchange Chromatography. 6. Affinity Chromatography. 7. Gel filtration Chromatography. 8. Enzyme Kinetics. 9. Electrophoresis. 10. Western Blots. 11. Restriction Enzymes. 12. Cloning and Expression of Foreign Proteins. 13. Polymerase Chain Reaction.

ANCILLARIES Experiments in Biochemistry: A Hands-On Approach, Second Edition features a variety of hands-on, classroom tested experiments that are proven to work and can be completed in a normal lab period. The manual’s stand-alone experiments are effective in courses meeting only once a week, giving students a broad overview of the subject matter. A more comprehensive set of experiments is also available and allows students to delve further into each of the topics presented. The Second Edition also features new and revised experiments, including a new experiment that involves cloning the barracuda LDH gene! Students and professors will also find expanded problem sets in this edition. “Tip” boxes, located throughout the text, provide pointers to students on how to perform the experiment at hand, while “Essential Information” boxes highlight pertinent information that will help the student complete the experiment. The second edition continues to include references and further readings at the end of each chapter.

NEW TO THIS EDITION In Experiment 12, students will clone the barracuda LDH gene into an expression vector, making a HIS-Tagged fusion protein that can be purified by affinity chromatography. Students will create a new vector for doing expression that makes the ligation of DNA easier and more efficient while learning about expanded methods for purification of HISTagged Lactate Dehydrogenase via Affinity Chromatography. The Second Edition includes expanded problem sets for further biochemistry practice and study.




BIOCHEMISTRY

KEY FEATURES All experiments have been classroom tested through multiple semesters and can be completed in a normal lab period. Alternate versions of experiments allow for easy use in labs which meet only once a week or multiple times in a week. “Tip” boxes throughout text give students pointers on how to perform the labs.

Print out the full lab at http://www.CERLabs.com

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A message from Rebecca Heider, CER Program Manager

A COMMITMENT TO SERVICE AND COMMUNITY At Brooks/Cole, we are committed to maintaining the level of service and excellence that has long characterized the CER program. With that in mind, we are continuing to work to enhance our delivery systems so that your experience in selecting, ordering, and receiving CER labs matches the excellence of the experiments themselves. The continued success of the CER program hinges on the involvement of the chemistry education community. Since CER was founded almost 20 years ago under the skilled leadership of Bruce Thrasher and continuing guidance of H. Anthony Neidig, hundreds of instructors have contributed to our database of over 300 experiments, whether by authoring, reviewing or class-testing experiments, or by simply providing us with ideas and feedback. We are reaffirming this commitment to serving the needs of the chemistry community, and we invite you to share your ideas and expertise with us and with the CER community as a whole. A Call for Contributors: If you have comments or suggestions for us, or if you are interested in authoring, reviewing, or class-testing a CER laboratory module, please contact me. I look forward to hearing from you!

THE SOURCE FOR CHEMISTRY LABORATORY INSTRUCTORS Chemical Education Resources (CER), the foremost publisher of customized chemistry laboratory manuals, offers quality, choice, economy, and the most extensive support system available for laboratory instruction. Hundreds of carefully developed experiments are available for a range of chemistry laboratory courses that includes Introductory Chemistry, Health Science Chemistry, General Chemistry, and Organic Chemistry. In addition, CER offers labs geared towards specific teaching methodology. For example, experiments from our Technology Series feature investigations that use probes to collect data directly and computers to process the data. Experiments from our Chemical Scenarios Series employ a guided inquiry approach, making the students responsible for more of the design and execution of the investigations.

HOICE AND CUSTOMIZABILITY You can select from more than 300 carefully crafted experiments to create an individualized laboratory manual. For commonly taught topics, a choice of several experiments is available, each taking a different approach or employing a different chemical system. Experiments range from the traditional to the unique, from the straightforward to the challenging, from the qualitative to the quantitative, allowing the instructor a wide array of choices. And if you don’t find the lab that exactly fits your needs, you can supplement your CER lab manual with your own experiments, or draw experiments from some of Brooks/Cole’s best-selling lab manuals.

XCELLENCE AND RELIABILITY Rebecca Heider, CER Program Manager Thomson Brooks/Cole 3501 Market Street, Philadelphia, PA 19104 Phone: 800.523.1850, x3781 Fax: 215.243.3786 Email: [email protected]

Every experiment we offer is selected and developed by our Series Editors—teaching chemists who oversee the development of labs in their own field of specialization. In addition, each experiment is rigorously evaluated for safety and accuracy, and student-tested under the supervision of a laboratory instructor.

ESOURCES FOR THE CHEMISTRY COMMUNITY We offer the most extensive support network in our business. Our carefully prepared Instructor’s Information Sheets include equipment and reagent requirements; instructions for solution preparation; spillage clean-up, hazard, and disposal information for the reagents and reaction products; comments and suggestions for using the experiments; representative student data; and answers to the Pre- and PostLaboratory Assignments. (See next page for details!)

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PROVEN FEATURES Over the years, the format of CER labs has been developed and refined based on user feedback and on advances in the field of chemistry education. As experiments are revised and updated and new labs published, careful attention is paid to improving the pedagogical features that have become the hallmark of CER’s Modular Laboratory Program in Chemistry. Developed by teaching chemists for teaching chemistry, CER pedagogy reflects our editorial team’s first-hand experience in the chemistry classroom. Continually updated, CER experiments offer the following remarkable features:

The experimental work is presented and done in the order in which a scientist would approach a problem—Background, Procedure, Data, Results, and Interpretation. In most cases, the experiments are “self-contained” in the sense that the Background sections provide all information necessary for understanding the experiment and answering the Pre-Laboratory Assignment.

In the Procedure section, CER

experiments offer students detailed step-by-step directions, making student error much less likely.

Labeled Figures accurately illustrate equipment and apparatus. The figures used in the modules are relevant to the specific laboratory setup and provide students with details that promote a successful laboratory experience. Tables provide information and templates for reporting data. Chemical Equations and Chemical Structures illustrate chemical systems for the current laboratory procedure.

Note Boxes, found in the margins, contain procedural fine points to help students obtain acceptable data and avoid common errors. Interpretation of Your Results is not just a summary of calculations, but encourages students to put observations and results in a broader perspective.

Each experiment is framed by Pre- and Post-Laboratory Assignments to help students get the most out of their time in the lab.

EXTRAORDINARY INSTRUCTIONAL SUPPORT Available for each CER experiment, in-depth Instructor’s Information Sheets offer the following essential features: To aid in ordering supplies and managing inventory, a detailed list of Reagents and Equipment is provided for each experiment. The Preparations section takes the burden off the instructor by giving all the precise instructions a lab technician would need for preparation. Chemical Handling sections give detailed instructions for spillage clean-up, waste disposal and hazards. Helpful Comments on the Experiment sections give instructors teaching suggestions, and additional information about common pitfalls, possible variations and substitutions.

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I especially have been sold on the integrity (selfcontained aspect) of the experiments… all anyone would need to know to run the lab should be there for student and instructor.

”

Kathleen Moe former Chemistry instructor and long-time CER Developmental Editor

“

Having looked at the lab offerings from many publishers, I can honestly say that not one that I’ve seen even comes close to providing the kind of information provided in the CER Instructor Information Sheets.

”

Dr. Marcia L. Gillette Lecturer in Chemistry and CER Introductory Chemistry Series Editor, Indiana University, Kokomo experiments are “triedThese and true. There’s nothing as disappointing to students as when experiments don’t work. These have been field-tested by independent instructors to assure that they do work! Plus, they are continually being updated.

”

Dr. Henry D. Schreiber Professor of Chemistry and CER General Chemistry Series Editor, Virginia Military Institute

Representative Student Data are given so lab instructors will have some idea what to expect before beginning the lab exercise. The Pre- and Post-Laboratory Quizzes feature a variety of questions from identification and understanding of terms to questions that prompt students to use critical thinking skills to anticipate the effects of experimental error on experimental outcome(s). Answers to the Pre-Lab Assignment, the Interpreting Your Results section, and the Pre- and Post-Laboratory Quizzes are also provided. Laboratory instructors can consult directly with an experiment author or Series Editor if they have any questions about an experiment. To contact any of our Series Editors, go to www.CERLabs.com. To access the Instructor’s Information Sheets for any of our labs, go to www.CERLabs.com.


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BUILD YOUR OWN CUSTOMIZED LAB MANUAL WITH www.CERLabs.com Search CER’s database, view experiments, access course resources, and build your custom lab manual at http://www.CERLabs.com. SEARCH THE DATABASE AND VIEW EXPERIMENTS

“

You can use only the labs you want, selected from a large number of possibilities. Your students do not have to pay for unused labs because a book had to be bought. CER labs can also be combined with your own experiments to customize a lab book for your course.

”

Dr. Joe S. Jeffers Professor of Chemistry and CER Organic Series Editor, Ouachita Baptist University

“

In many cases there is a selection of experiments available to illustrate a fundamental chemical concept, making it possible for lab instructors to vary the experiments from year to year. This helps overcome the ‘fraternity file’ problem where students can simply copy answers from materials turned in by their friends who have already been through the course.

”Dr. Marcia L.

Gillette Lecturer in Chemistry and CER Introductory Chemistry Series Editor, Indiana University, Kokomo

To ensure that your lab manuals arrive in time for classes, please place your order at least 6 weeks prior to the start of class.

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At www.CERLabs.com, go to “Browse Experiments”, where you can search our database of more than 300 experiments by keyword, course, topic, or difficulty level to find exactly the experiments you are looking for. You can read an abstract, view the entire lab, or print out a review copy.

ACCESS UNPARALLELED INSTRUCTOR RESOURCES At www.CERLabs.com you can not only access CER’s outstanding Instructor Information Sheets, but also contact our CER Series Editors with your questions or comments. Additional resources on the site include downloadable techniques videos, equipment simulations, teaching tips, and information about authoring labs for CER. All instructor resources, including printable review copies of labs, are password protected. Contact us to get a password.

LEARN MORE ABOUT OTHER OFFERINGS FOR YOUR CHEMISTRY COURSE At www.CERLabs.com you can learn more about related products for your chemistry course, including our Lab Notebooks, Lab Handbook, and all of our Brooks/Cole chemistry textbooks and technology products.

BUILD A CUSTOM LAB MANUAL AND INITIATE YOUR ORDER STEP : SEARCH / VIEW / SELECT Go to the “Manual Builder” and search for the experiments you want to include. Select each experiment and click the “Add to Custom Manual” button.

STEP : EDIT MANUAL Once you’ve made your selections, click on the “Step 2: Edit Manual” tab at the bottom of the page. On this page you can see more information about each lab, and arrange the labs in the order you prefer. You can also insert placeholders for adding your own material.

STEP : INITIATE ORDER When you’ve finalized your choices, click on the “Step 3: Initiate Order” tab at the bottom of the page. On this page you will fill out your course information and send your selections to us. A custom publishing representative will contact you with your ISBN within two business days. (NOTE: Customers ordering the same manual they’ve used in the past can simply provide their existing ISBN to the bookstore for ordering.)

If you have questions about the CER Web site, or if you need a password, call Rebecca Heider at 1-800-523-1850 ext. 3781. If you already have an ISBN and are ready to place your order, contact Thomson Custom Publishing at 1-800-355-9983.


CHEMICAL EDUCATION RESOURCES First-Year Labs Experiment Descriptions

Symbols in the margin next to the abstracts indicate the course(s) for which the experiment is most appropriate. Experiments are arranged by code number. The courses include:

INTRODUCTORY CHEMISTRY Students with little or no chemistry laboratory experience may take this course to prepare for the general chemistry sequence, as the inorganic portion of a health science course, or as the first part of the science majors laboratory.

ANALYSIS

ANAL 215

Dipeptide and Amino Acid Identification by Paper Chromatography (Revised) Leallyn B. Clapp, Brown University Various dipeptides and amino acids will be identified by paper chromatography. (2 hrs.)

ANAL 237

HEALTH SCIENCES CHEMISTRY A one- or two-term course for students in nursing or the allied health sciences.

GENERAL CHEMISTRY The year-long sequence taken by physical and biological science majors, most of whom will have had some high school chemistry laboratory experience. (Students using experiments described as “advanced” should have extensive laboratory experience with an analytical emphasis.)

Physiologically Important Anions A.L. Kemppainen, Finlandia University Chemical reactions are used to identify bicarbonate, chloride, iodide, phosphate, and sulfate ions in solution. Students identify an unknown anion in solution and test various commercial products for these anions. (1.5–2 hrs.)

ANAL 238

Determining Ascorbic Acid in Vitamin C Tablets A. L. Kemppainen, Finlandia University The mass percent of ascorbic acid in a vitamin C tablet is determined by titration with a standardized sodium hydroxide solution. Instructions are included for using a buret. (1.5 hrs.)

ORGANIC CHEMISTRY The course for science majors who are continuing their study of chemistry after completing a year of college-level general chemistry or the equivalent.

In addition to symbols that indicate courses, you will also find a number of experiments marked with:

Classifying Carbohydrates William M. Loffredo, East Stroudsburg University Qualitative tests are used to classify carbohydrate solutions. Six known carbohydrates are characterized and an unknown carbohydrate is identified. (2–2.5 hrs.)

ANAL 241

TECHNOLOGY Experiments marked with this symbol require special equipment (such as probes, calculators, or computers) and are part of our new technology series.

Introductory Chemistry

ANAL 239

Health Sciences Chemistry

Rennin Activity A. L. Kemppainen, Finlandia University The curdling of milk by the enzyme rennin is studied. Students observe how factors such as temperature, concentration, and pH influence enzyme activity. (1.5 hrs.)

General Chemistry

Organic Chemistry


EXPERIMENT DESCRIPTIONS

FIRST YEAR L ABS


Technology

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CHEMICAL EDUCATION RESOURCES


First-Year Labs Experiment Descriptions

ANAL 242

ANAL 356

DNA Extraction

Gravimetric Determination of Sulfate

A. L. Kemppainen, Finlandia University

James N. Spencer, Franklin and Marshall College

DNA is extracted from onion cells. A qualitative test is used to detect DNA in the sample. (1–1.5 hrs.)

The percent sulfate in an unknown solid is determined by the classical precipitation of sulfate as BaSO4. (4 hrs.: advanced)

ANAL 304

ANAL 357

Evaluation of Vinegar Samples

Spectrophotometric Determination of Copper in Brass

H.A. Neidig, Lebanon Valley College The percent acetic acid in a group of commercial vinegar samples is determined by titrimetry and the data are used to evaluate the vinegar samples. (2 hrs.)

E. J. Billingham, formerly of University of Nevada, Las Vegas

ANAL 322

ANAL 358

Determining Aluminum(III) Concentration in Natural Water

A Beer’s Law Study

Kenneth E. Borst, Rhode Island College

The concentration range over which Beer’s law is applicable for the copper (II) ion–aqueous ammonia system is determined. The molar absorptivity is calculated for the absorbing substance. (3 hrs.)

A standard absorption curve for the aluminum(III)– Eriochrome Cyanine R complex will be prepared. The curve will be used to determine the Al(III) ion concentration in samples of natural and treated water. (2–3 hrs.)

David P. Dingledy, SUNY College, Fredonia

ANAL 359 ANAL 335

Analysis of a Hydrogen Peroxide Solution George Deckey, Rhode Island College A KMnO4 solution is standardized and used to analyze an H2O2 solution. (2.5 hrs.)

ANAL 349

Spectrophotometric Analysis of Permanganate Solutions Donald F. Clemens, East Carolina University, and Warren A. McAllister, Burroughs Wellcome Co., Greenville, NC After determining the analytical wavelength of MnO4– ion, measurements are made from which a Beer’s law plot is prepared and used in the determination of the concentration of an unknown MnO4– ion solution. (3 hrs.)

Standardizing a Hydrochloric Acid Solution Norman E. Griswold, Nebraska Wesleyan University An introduction to standard solutions in which a HCl solution is standardized by titration with solutions prepared from sodium carbonate, a primary standard. (3 hrs.)

ANAL 360

A Colorimetric Determination of Aspirin in Commercial Preparations Robert P. Pinnell, Claremont McKenna, Scripps, and Pitzer Colleges

ANAL 350

Standardizing a Sodium Hydroxide Solution Norman E. Griswold, Nebraska Wesleyan University

From percent transmittance measurements, a Beer’s law plot is prepared and used in the determination of aspirin in commercial products. (3 hrs.)

A NaOH solution is standardized by titration with a standard HCl solution. (3 hrs.)


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The mass percent of Cu in a commercial brass alloy is determined spectrophotometrically. (3 hrs.: advanced)


General Chemistry

Organic Chemistry

Technology



ANAL 367

Spectrophotometric Studies of Food Dye Solutions

The Chemistry and Qualitative Analysis of Anions

M. L. Gillette, Indiana University, Kokomo, and H. A. Neidig, Lebanon Valley College

James G. Boyles, Bates College; Judith C. Foster and David S. Page, Bowdoin College

After determining the analytical wavelengths for several food dyes, measurements are made from which Beer’s law plots are prepared and used to determine the concentration of an unknown dye solution. (2–3 hrs.)

The chemistry of selected anions (Cl-, Br-, I-, SO42-, CO32-, SO32-, PO43-, NO2-, and NO3- ions) is developed. A procedure is established for qualitatively verifying the presence of these selected anions in an unknown solution. (4 hrs.)

ANAL 364

ANAL 378

The Chemistry and Qualitative Analysis of Cations: Group Separations and Separation of Group I Cations

Determining the Percent Composition of an Aqueous Hydrogen Peroxide Solution

James G. Boyles, Bates College; Judith C. Foster and David S. Page, Bowdoin College The chemistry of cation Groups I, II, and III is developed. The separation of Groups I, II, and III is demonstrated using Ag+, Cu2+, and Fe3+ ions. A procedure is established for qualitatively verifying the presence of Ag+, Hg22+, and Pb2+ ions in an unknown solution. (4 hrs.)

John H. Bedenbaugh, Thomas S. Heard, and Angela O. Bedenbaugh, University of Southern Mississippi The percent H2O2 in an aqueous solution is determined by collecting a measured volume of oxygen produced from the quantitative, yeast-catalyzed decomposition of H2O2. This volume is related to the stoichiometry of the reaction and to the gas laws. (2–3 hrs.)

ANAL 394 ANAL 365

The Chemistry and Qualitative Analysis of Cations: Group II James G. Boyles, Bates College; Judith C. Foster and David S. Page, Bowdoin College The chemistry of selected Group II cations (Bi3+, Cu2+, Cd2+, and Sn4+ ions) is developed. A procedure is established for qualitatively verifying the presence of these selected cations in an unknown solution. (4 hrs.)

Determining the Molar Concentration of a Sodium Hydroxide Solution H. A. Neidig, Lebanon Valley College, and J. N. Spencer, Franklin and Marshall College The molar concentration of a sodium hydroxide solution is determined by titrating a potassium hydrogen phthalate solution. The experiment includes extensive information on the techniques of using a buret. (2 hrs.)

ANAL 395 ANAL 366

Titrating Vinegar

The Chemistry and Qualitative Analysis of Cations: Groups III and IV

H. A. Neidig, Lebanon Valley College, and J. N. Spencer, Franklin and Marshall College

James G. Boyles, Bates College; Judith C. Foster and David S. Page, Bowdoin College

The molar concentration of acetic acid in a vinegar sample is determined by titration with a standard sodium hydroxide solution. Extensive information on the technique of using a pipet is included. (2 hrs.)

The chemistry of selected Group III and IV cations (Fe2+/Fe3+, Ni2+, Cr3+, Ba2+, and Ca2+ ions) is developed. A procedure is established for qualitatively verifying the presence of these selected cations in an unknown solution. (4 hrs.)



General Chemistry

Organic Chemistry



ANAL 361

Technology

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ANAL 396

ANAL 424

Introducing the Qualitative Analysis of a Group of Cations

Standardizing a Sodium Hydroxide Solution with Oxalic Acid

H. A. Neidig, Lebanon Valley College, and J. N. Spencer, Franklin and Marshall College

Norman E. Griswold, Nebraska Wesleyan University

A procedure is developed to detect the presence of barium, lead(II), and iron(III) ions in solution. The procedure is used to identify the components of an unknown solution containing one or more of these ions. (2–3 hrs.)

ANAL 403

Estimating the Copper Content of Malachite Using Microscale Techniques S.K. Gunter, Scottsdale, AZ, and James P. Birk, Arizona State University The copper content of a malachite ore is estimated using small scale colorimetry. (1.5–2 hrs.)

ANAL 415

Introducing Volumetric Techniques by Analyzing Bleaching Solution

ANAL 425

Titrating Hydrochloric Acid Solution with a Standard Sodium Hydroxide Solution Norman E. Griswold, Nebraska Wesleyan University The concentration of a hydrochloric acid solution is determined using standard sodium hydroxide solution. Calculations involve equivalents and normality. Directions are given to the students for processing their titration mixtures and rinses for disposal. The sodium hydroxide solution standardized in ANAL 424 can be used in this experiment. (3 hrs.)

Enno Wolthuis, Calvin College

ANAL 426

Techniques are developed for quantitative volume measurement using a buret, a pipet, and a volumetric flask. This glassware is used to make a dilution and to determine the percent sodium hypochlorite in a commercial bleaching solution. (3 hrs.)

Standardizing a Sodium Hydroxide Solution with a Standard Hydrochloric Acid Solution

ANAL 416

Determining the Percent Sodium Hypochlorite in Commercial Bleaching Solutions Enno Wolthuis, Calvin College The percent sodium hypochlorite in commercial bleaching solutions is determined by iodometric titration. The cost effectiveness of different brands of commercial bleaching solutions are compared. (3 hrs.)

Andrew W. Zanella, Claremont McKenna, Pitzer, and Scripps Colleges The molarity of an NaOH solution is determined by titrating the solution against a known volume of a standard HCl solution. Extensive information is given for using a buret. Calculations involve molarity. Directions are given to the students for processing their titration mixtures and rinses for disposal. The standardized sodium hydroxide can be used in ANAL 427. (2 hrs.)

ANAL 427

Quantitatively Determining the Acid Content of Fruit Juices

ANAL 417

Using Volumetric Glassware to Measure, Dilute, and Titrate an Acid Solution Richard S. Mitchell, Arkansas State University Laboratory techniques are developed for using volumetric glassware. The acid concentration of a solution is determined by diluting the solution and titrating an aliquot of the diluted solution with standard sodium hydroxide. (2 hrs.) Introductory Chemistry

42

A sodium hydroxide solution is standardized by titrating solutions prepared from oxalic acid dihydrate, a primary standard. Calculations involve equivalents and normality. Directions are given to the students for processing their titration mixtures and rinses for disposal. The standardized sodium hydroxide can be used in ANAL 425. (3 hrs.)


Andrew W. Zanella, Claremont McKenna, Pitzer, and Scripps Colleges The apparent citric acid concentration in a variety of fruit juices is determined by titration with the standard NaOH solution prepared in ANAL 426. The apparent citric acid content of different fruit juices is compared. Directions are given to the students for processing their titration mixtures and rinses for disposal. (2 hrs.)

General Chemistry

Organic Chemistry

Technology



ANAL 462

Determining Water Hardness by EDTA Titration

Nonsulfide Qualitative Analysis of Cations: Separating and Identifying Representative Cations From Groups A–E

Constance Suffredini, University of California, Irvine Water hardness–total, permanent, and temporary–are discussed and determined by water sample analysis for Ca2+ and Mg2+ ion concentration, using EDTA titrations with Erio T indicator. (3 hrs.)

ANAL 437

Evaluating the Calcium Ion Content in Commercial Dried Milk Powders David N. Bailey, Illinois Wesleyan University Ca2+

EDTA titration reaction forms a complex ion with ion in milk samples. Number of moles, mass percent, and cost per ounce of Ca2+ ion for each sample are calculated and compared to the data for other samples. (3 hrs.)

ANAL 442

Judith C. Foster, Bowdoin College Representative ions from six cation groups are separated. The presence of each cation in a known mixture is verified. The presence or absence of each cation in an unknown mixture is verified. (2–3 hrs.)

ANAL 463

Nonsulfide Qualitative Analysis of Cations: Separating and Identifying Representative Group A Cations (Hg22+, Ag+, and Pb2+) Judith C. Foster, Bowdoin College Differences among the chemical behaviors of the Group A cations are used to separate and identify these cations present in known and unknown mixtures. (2–3 hrs.)

Analyzing Food Products for Vitamin C Roberta G. Reed, The Mary Imogene Bassett Hospital, and John C. Kotz, SUNY, Oneonta Juice and solid food samples are analyzed for ascorbic acid content by oxidation–reduction titration. The amount of vitamin C per serving and the %RDA for each sample are calculated. (2 hrs.)

ANAL 445

Separation and Identification of Food and Drug Dyes by TLC

ANAL 464

Comparing the Resistance of Buffered and Unbuffered Solutions to pH Change Marcia L. Gillette, Indiana University Kokomo Small scale techniques are used to compare the capacity of water, the individual components of a buffer system, and buffer systems to resist pH change upon addition of acidic or basic solutions. (2 hrs.)

Harold T. McKone, Saint Joseph College, CT

ANAL 466

Artificial dyes used to color foods and drugs are extracted and quantitatively identified by thin-layer chromatography. (2 hrs.)

Standardizing a Sodium Hydroxide Solution and Using It to Analyze Vinegar Marcia L. Gillette, Indiana University Kokomo

ANAL 455

Separating and Determining the Mass of Calcium Ion in a Calcium-Enriched Tablet

Small scale techniques are used to standardize a NaOH solution by titration against a standard potassium hydrogen phthalate solution. The standardized NaOH solution is used to determine the acetic acid content of commercial vinegar. (2 hrs.)

M. L. Gillette, Indiana University Kokomo, and H. A. Neidig, Lebanon Valley College A calcium-enriched tablet is dissolved and the calcium ion is precipitated as calcium carbonate. The masses of calcium carbonate and calcium are determined. The mass percent of calcium ion in the tablet is calculated and compared with that listed on the label. The filtrate is treated for disposal. (2–2.5 hrs.)



ANAL 478

Evaluating Commercial Antacids


ANAL 436

David N. Bailey, Illinois Wesleyan University The moles of hydrochloric acid neutralized by a commercial antacid tablet are determined by a back titration procedure. The mass effectiveness and cost effectiveness of the tablet are calcu-

General Chemistry

Organic Chemistry


Technology

43

CHEMICAL EDUCATION RESOURCES First-Year Labs Experiment Descriptions lated. The cost effectiveness of different brands of antacids are compared. (3 hrs.)

Separating Selected Metal Cations by Paper Chromatography


ANAL 479

Determining the Formula of an Ionic Hydrate Gravimetrically Donald F. Clemens, East Carolina University, Warren A. McAllistar, Burroughs Wellcome Co., Greenville, NC, and M.L. Gillette, Indiana University Kokomo The mass percent of water of hydration in an unidentified ionic hydrate is determined. The formula of the hydrate is established. (3 hrs.)

Frank Rioux, Saint John’s University, Collegeville, MN, and Judith C. Foster, Bowdoin College The retention factor is determined for four transition-metal cations. Cations in unknown solutions are separated by paper chromatography and identified, using spot tests and retention factors. (2.5 hrs.)

ANAL 501

Determining the Effects of Cooking on the Vitamin C Content of Green Pepper

ANAL 483

Diagnosing Disease Using Kinetic Enzyme Assays Owen A. Moe, Lebanon Valley College, and Kathleen K. Moe, Chemical Education Resources Kinetic enzyme assays are carried out for the marker enzyme alkaline phosphatase in two simulated human blood serum samples, normal and patient. The clinical significance of the assay results are assessed. (2 hrs.)

Todd P. Silverstein, Willamette University, and Eric R. Johnson, Ball State University An oxidation–reduction titration is used to determine how four different cooking methods affect the vitamin C content of green pepper. (3 hrs.)

ANAL 503

Nine Bottles: An Adventure in Chemical Identification

ANAL 492

Separating and Identifying Food Dyes by Paper Chromatography Peter G. Markow, St. Joseph College, CT The retention factors of seven pure food dyes are determined in three different solvent systems. The most effective solvent for separating all seven dyes is determined. Dyes in unknown mixtures and selected commercial products are separated and identified, using paper chromatography. (2–3 hrs.)

Jay Young, Chemical Consultant, H.A. Neidig, Lebanon Valley College, and William Loffredo, East Stroudsburg University An analysis scheme is developed to identify the solute in each of nine unknown solutions. Identifications are made based on observations of small amounts of the nine solutes, first mixed as known solutions, then mixed as nine unknown solutions, and a comparison of the two sets of observations. In some cases, a third solution is used for a confirmatory test. (3 hrs.: advanced)

ANAL 517 ANAL 493

Analyzing a Mixture of Sodium Hydrogen Carbonate and Sodium Chloride by Thermal Decomposition John T. Yoke, Oregon State University, and M. L. Gillette, Indiana University Kokomo The percent NaHCO3 in an unknown mixture of NaHCO3 and NaCl is determined gravimetrically. (2–2.5 hrs.)


44

ANAL 498


Determining the Water Content of an Ionic Hydrate Donald F. Clemens, East Carolina University; Warren A. McAllister, Burroughs Wellcome Co.; Marcia L. Gillette, Indiana University Kokomo; and Henry D. Schreiber, Virginia Military Institute The mass percent of water in an ionic hydrate is determined by heating a sample to constant mass to release its waters of hydration. The chemical formula of the ionic hydrate is also established. (3 hrs.)

General Chemistry

Organic Chemistry

Technology



ANAL 622

Qualitative Analysis of Cations

Analyzing the Vitamin C in Fruit Juices

Michael J. Fields, Louisiana State University at Alexandria

M.L. Gillette, Indiana University Kokomo, Roberta G. Reed, The Mary Imogene Bassett Hospital, and John C. Kotz, SUNY Oneonta

Non-sulfide qualitative analysis scheme for nine cations. The presence of each cation in a known mixture is verified. The presence or absence of each cation in an unknown mixture is then identified. (5 hrs.)

A DCP solution is standardized. The amount of vitamin C in fruit juice is determined by oxidation-reduction titration with the standardized DCP solution. (1.5 hrs.)

ANAL 605

Determining the Percent Water in an Unknown Hydrate

ANAL 624

Identifying Cations in a Solution

M.L. Gillette, Indiana University Kokomo, H.A. Neidig, Lebanon Valley College, and J.N. Spencer, Franklin and Marshall College

H.A. Neidig, Lebanon Valley College, J.N. Spencer, Franklin and Marshall College, and M.L. Gillette, Indiana University Kokomo

The percent water in an unknown hydrate is determined. (1.5–2 hrs).

A procedure using chemical reactions to detect the presence of barium, lead(II), and iron(III) ions in solution is developed. Students identify these cations in an unknown solution, and write chemical equations for the observed reactions. (1.5 hrs.)

ANAL 618

Standardizing a Sodium Hydroxide Solution M.L. Gillette, Indiana University Kokomo, H.A. Neidig, Lebanon Valley College, and J.N. Spencer, Franklin and Marshall College Measured masses of potassium hydrogen phthalate are titrated with NaOH. The data are used to calculate the molarity of the NaOH solution. Instructions are included for using a buret. (1–1.5 hrs.)

ANAL 625

Estimating the Acid Content of Fruit Juices Andrew W. Zanella, Claremont McKenna, Pitzer, and Scripps Colleges, and M.L. Gillette, Indiana University Kokomo The acid content of a fruit juice is estimated by titration with standardized sodium hydroxide solution. (1.5 hrs.)

NEW! ANAL 638 ANAL 610

Titrating the Acetic Acid in Vinegar M.L. Gillette, Indiana University Kokomo, H.A. Neidig, Lebanon Valley College, and J.N. Spencer, Franklin and Marshall College Standardized NaOH solution is used to titrate measured volumes of vinegar. The molarity of acetic acid in vinegar is calculated from the titration data. (1–1.5 hrs.)

Determining the Acid-Neutralizing Capacity of Common Antacids David N. Bailey, Illinois Wesleyan University TThe acid-neutralizing capacity of an antacid tablet is determined in terms of the mass percent of calcium carbonate present by adding an excess of hydrochloric acid solution and backtitrating with sodium hydroxide solution. (1.5 hrs.)

ANAL 900 ANAL 620

Separating and Identifying FD&C Dyes Using Paper Chromatography Peter Markow, Saint Joseph College, and M.L. Gillette, Indiana University Kokomo The retention factors (Rf) of FD&C dyes are determined. Students separate and identify these dyes in unknown mixtures and selected commercial products. (1–1.5 hrs.) Introductory Chemistry


Determining Dolomite Composition by Thermal Decomposition Patricia A. Metz, University of Georgia


NEW! ANAL 523

A sample of dolomite is heated. From the decrease in mass, the mass percents of the magnesium carbonate and calcium carbonate in the sample are determined. (2.5 hrs.) SCENARIO: Geologists for the National Mineral Company need assistance analyzing samples of dolomite from a General Chemistry

Organic Chemistry


Technology

45



newly-discovered deposit to determine mass percents of magnesium carbonate and calcium carbonate. Based on the results, production cost, and selling price, the students write a memo to the company geologists indicating whether or not the new deposit can be developed profitably.

ANAL 902

ELECTROCHEMISTRY

Analyzing the Acetic Acid Content of Vinegar Patricia A. Metz, University of Georgia The molarity and mass percent acetic acid in a vinegar sample are determined by titrating with a standard sodium hydroxide solution. (3 hrs.) SCENARIO: A plant worker at Nature’s Best Vinegar Company accidentally diluted a batch of distilled vinegar too much for it to be sold. However an undiluted batch is available. The company quality control staff needs the students’ help analyzing the bad batch and determining how to blend the two batches to produce a vinegar that meets the specifications for sale. Students write a memo of their findings to the plant manager.

ELEC 224

Determination of the Molecular Mass of Lead by Electrolysis H.A. Neidig, Lebanon Valley College, and J.N. Spencer, Franklin and Marshall College The molecular mass of Pb will be calculated from data obtained from the electrolysis of a Pb(NO3)2 solution. (3 hrs.)

ELEC 418

ANAL 904

Studying Electrochemical Cells and Reduction Potentials

Separating the Components of Beach Sand

R. L. Marks, University of Arizona

Patricia A. Metz, United States Naval Academy

The reduction potentials are determined for Fe2+(aq) + 2 e– Fe(s), Cu2+(aq) + 2 e– Cu(s), and Pb2+(aq) + 2 e– Pb(s) half reactions from appropriate cell potentials and selected standard reduction half reactions. The predicted and measured potentials are compared to cells constructed from combinations of these three half reactions. (3 hrs.)

A mixture of sand, sea salt, and crushed seashells are separated and recovered. The mass percent of each component in the mixture and the total mass percent recovery are determined. (2.5–3 hrs.) SCENARIO: The Introduction to Glassmaking course at the State Art Institute is making soda-lime-silica glass from beach sand. The art professor needs assistance analyzing the mass percent of sand, sea salt, and seashells in beach sand she brought back from her summer vacation. The mass percentages are used to calculate the additional soda, lime, and silica needed to reach a target recipe. Students write a report of their finding to the art professor.

NEW! ANAL 909

Determining the Thickness of Zinc on Galvanized Washers

ELEC 419

Studying Electrochemistry and Establishing the Relative Reactivity of a Series of Metals J. N. Spencer, Franklin and Marshall College and H. A. Neidig, Lebanon Valley College The relative electromotive potentials of a series of metals is studied by observing the direction of electron transfer when two metals, each suspended in a solution of its ions, are connected in a closed electrical system. Based on observations chemical equations are written for the cell reactions. (3 hrs.)

Patricia A. Metz, University of Georgia Students write a quality control report either supporting or rejecting a company’s contract bid to produce galvanized washers. The zinc coating on a galvanized washer is removed chemically. From the decrease in mass and the original dimensions of the washer, the millimeters of zinc coating and the number of layers of zinc atoms are determined. (1.5 hrs.)


46

SCENARIO: Consolidated metal is submitting a bid for a government contract to make 250,000 galvanized washers a year for three years. The company needs assistance verifying their washers meet the governments specifications for consistent thickness. Students write a quality control report either supporting or rejecting the contract bid.


General Chemistry

Organic Chemistry

Technology



Studying Electrochemical Half-Cells and HalfReactions

EQUL 308

Henry Schreiber, Virginia Military Institute, James N. Spencer, Franklin and Marshall College, and H. Anthony Neidig, Lebanon Valley College

Solubility Product Constant of Lead(II) Iodide

Three half cells are constructed. Equations are written for the half-reactions and the net oxidation–reduction reactions for the half-cells. The net potentials for the half-cells are determined. The three metals studied are ranked according to ease of oxidation. (1–2 hrs.)

The solubility product constant of PbI2 is calculated from data obtained from the titration of Pb(NO3)2 solutions with a standard solution of KI. (3 hrs.: advanced)

Kenneth A. Mantei and Ralph H. Petrucci, California State University San Bernardino

EQUL 342 ELEC 510

Studying the Temperature Dependence and Thermodynamics of Electrochemical Cells Clyde R. Metz, College of Charleston The electrode potentials for two half-cells are determined and used to predict the potential for a third cell. The experimental and predicted potentials are compared. The temperature dependence of the cell potential is measured and used to determine G, S, and H for the cell reaction. The voltages of a concentration cell and a thermocell are measured and the thermoelectric power of the thermocell is calculated. (2 hrs.)

Determination of the Solubility Product Constant of a Salt Judith C. Foster, Bowdoin College The solubility product constant of potassium hydrogen tartrate is determined using titrimetry. (2 hrs.)

EQUL 343

Determining an Equilibrium Constant Using Spectrometry Norman J. Hudak, Willamette University

ELEC 905

Devising a Reduction Potential Table

The equilibrium constant is determined for the reaction of Fe(III) and SCN– ions to form the thiocyanatoiron(III) complex ion, using spectrophotometric data. (3 hrs.)

Patricia A. Metz, United States Naval Academy Electrochemical cells are constructed from five different unknown metals and their respective metal salt solutions. The cell potentials are used to establish a reduction potential series for the five metals. (2.5–3 hrs.)

EQUL 376

SCENARIO: Intergalactic Mining Limited has discovered five new metals on the planet Metwen. The metallurgist needs help determining the reduction potential of each metal. Students build electrochemical cells from pairs of the metals. The cell potentials are used to establish a reduction potential series. Students write a report to the metallurgist detailing the logic they used to devise their series.

Donald C. Raney, Cañada College, and M. L. Gillette, Indiana University Kokomo

Determining the Dissociation Constant of a Weak Acid Using pH Measurements

The acid dissociation constant and the identity of an unknown weak acid are determined from pH measurements. (3 hrs.)

EQUL 392

Introducing Equilibrium H.A. Neidig, Lebanon Valley College, and J.N. Spencer, Franklin and Marshall College From observations, the effect of change on a chemical system in equilibrium is determined and considered in terms of LeChâtelier’s principle. (2–3 hrs.)



General Chemistry

Organic Chemistry



EQUILIBRIUM

ELEC 450

Technology

47


EQUL 397

EQUL 441

pH, Acids, and Bases

Evaluating the Equilibrium Constant for the Reaction of Iron(III) Ion with Thiocyanate Ion


H. A. Neidig, Lebanon Valley College, and J. N. Spencer, Franklin and Marshall College The pH of solutions of acids, bases, and salts is estimated by observing the color of several indicators in these solutions. The solutions are arranged in order of their relative acidity or basicity. (2–3 hrs.)

EQUL 400

Estimating the Solubility Product Constant of Strontium Iodate Using Microscale Techniques M.L. Gillette, Indiana University Kokomo, and H. Anthony Neidig, Lebanon Valley College A solubility product constant is estimated for strontium iodate from solubility data. (2 hrs.)

Standard solutions of FeNCS2+ ion are prepared. A spectrophotometer is used to determine the %T of each solution, and the data are used to prepare a Beer’s Law plot. Five equilibrium mixtures are prepared, and the Keq for each mixture is measured and compared. An equilibrium constant expression for the reaction is written. Reaction mixtures are processed by the students for disposal. (2.5–3 hrs.)

EQUL 443

Studying the Effect of Buffering on the Resistance of a Solution to pH Change William E. Good, Jr., and George S. Patterson, Suffolk University, MA

EQUL 402

Evaluating the Dissociation Constant of a Weak Acid Using Microscale Techniques M.L. Gillette, Indiana University Kokomo, and H. Anthony Neidig, Lebanon Valley College

A buffer is prepared. HCl and NaOH solutions of varying molarities are added to the buffer and to distilled water. The pH of each mixture is measured with pH paper, indicators, and a pH meter, and the data are plotted. Solutions are processed by the students for disposal. (3 hrs.)

The dissociation constant of a weak acid is evaluated using pH measurements. (2 hrs.)

EQUL 453

EQUL 404

Determining the Equivalent Mass and Dissociation Constant of an Unknown Weak Acid by Titrimetry

Studying Chemical Equilibria and Applying LeChâtelier’s Principle Using Microscale Techniques

Richard C. Bell, Lebanon Valley College, and M. L. Gillette, Indiana University Kokomo

M.L. Gillette, Indiana University Kokomo, and H. Anthony Neidig, Lebanon Valley College

A NaOH solution is prepared, standardized, and used to obtain titration data for an unidentified acid. From these data, the equivalent mass and pKa are determined and used to identify the acid. (6 hrs.)

The effect of a change in a reaction condition on a chemical system at equilibrium is determined. The observed responses are correlated with LeChâtelier’s principle. (2 hrs.)

EQUL 465

Using Acid–Base Indicators to Visually Estimate the pH of Solutions

EQUL 411

Estimating the pH of Household Products Using Red Cabbage Extract as an Indicator

Marcia L. Gillette, Indiana University Kokomo Small scale techniques and acid–base indicators are used to visually estimate the pH of various solutions. (2 hrs.)

Leslie Farrer, Santa Rosa, CA A pH color scale is established for the wide range acid–base indicator extracted from red cabbage. A cabbage extract indicator solution is used to estimate the pH of a variety of household products. (1.5–2 hrs.)


48

Conrad H. Bergo, Michael P. Doherty, William M. Loffredo, and Robert F. Schramm, East Stroudsburg University


General Chemistry

Organic Chemistry

Technology



Determining the Common Ion Effect on the Solubility of Potassium Hydrogen Tartrate Charles J. Marzzacco, Rhode Island College The solubility of potassium hydrogen tartrate is determined in a set of aqueous solutions containing various amounts of sodium chloride and potassium chloride. The solubility product constant for potassium hydrogen tartrate in these solutions is calculated. (2 hrs.)

EQUL 616

Introducing Chemical Equilibrium M.L. Gillette, Indiana University Kokomo, H.A. Neidig, Lebanon Valley College, and J.N. Spencer, Franklin and Marshall College Three chemical systems at equilibrium are disturbed. The observed effects are related to LeChâtelier’s principle. (1–1.5 hrs.)

EQUL 494

Monitoring Acid–Base Titrations with a pH Meter

EQUL 617

John W. Alcock, Quinnipiac College, and M. L. Gillette, Indiana University Kokomo

Estimating the pH of Some Solutions Using Visual Indicators

Titrant volume for titrations of HCl and NaOH and acetic acid and NaOH are collected and used to prepare titration curves that are used to compare the behavior of the two acids. (2–3 hrs.)

M.L. Gillette, Indiana University Kokomo, H.A. Neidig, Lebanon Valley College, and J.N. Spencer, Franklin and Marshall College The color of indicators in solutions of acids, bases, and salts is used to estimate pH. The solutions are arranged in order of their relative acidity or basicity. (1–1.5 hrs.)

EQUL 499

Studying the pH of Strong Acid, Weak Acid, Salt, and Buffer Solutions Norma Robinson North, State University of New York at Potsdam, and M. L. Gillette, Indiana University Kokomo The pH of several solutions is measured and used to calculate a dissociation constant and a hydrolysis constant. The chemistry of a buffer system is studied by using pH measurements. (3 hrs.)

EQUL 519

Determining the pKa of an Acid–Base Indicator George S. Patterson, Suffolk University A spectrophotometer is used to measure the concentrations of the acid and base forms of bromophenol blue in solutions with different pH. The weak acid equilibrium constant, as expressed by the pKa, is then determined for bromophenol blue. (3 hrs.)

EQUL 853, 855, 857, 859

Identifying a Weak Acid by Titrimetry R. C. Bell, Lebanon Valley College, M . L. Gillette, Indiana University Kokomo, and J. R. Crook, Western Washington University The sample size of an unknown acid is determined for a 25-mL titration with NaOH solution. The pH probe is calibrated and the system used to obtain pH/volume data from which a titration curve is printed. The first derivative of the curve is used to determine the equivalence point. From the half-equivalence point and these data, the pH, pKa, and the equivalent mass of the acid are found and used for identification. (2.5 hrs.) EQUL 853. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . CBL EQUL 855 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . LW/Win (M) EQUL 857 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Vernier LP EQUL 859 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . LW/Win (D)

NEW! EQUL 526

Equilibrium between Two Coordination Complexes of Co2+ in Solution

EQUL 865, 867, 869, 871

Henry D. Schreiber, Virginia Military Institute

J. W. Alcock, Quinnipiac College, M. L. Gillette, Indiana University Kokomo, and J. R. Crook, Western Washington University

The equilibrium constant is determined and Le Chatelier’s principle is demonstrated for the tetrahedral-to-octahedral conversion of Co2+ in mixtures of methanol and 2-propanol. The tetrahedrally coordinated Co2+ concentrations are monitored



Acid–Base Titration Curves


spectrophotometrically in the solutions, after calibration by a Beer’s law plot. (2.5 hrs.)

EQUL 487

The pH probe is calibrated with two buffer solutions of known pH. The system is used to prepare a pH/volume of NaOH titra-

General Chemistry

Organic Chemistry


Technology

49



First-Year Labs Experiment Descriptions tion curve for a NaOH/HCl titration. From the titration curve, the equivalence-point volume is used to calculate the original concentration of HCl. (2.5 hrs.) EQUL 865. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . CBL EQUL 867 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . LW/Win (M) EQUL 869 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Vernier LP EQUL 871 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . LW/Win (D)

KINETICS KINE 429

MISC 153

Logarithms Antony C. Wilbraham, Southern Illinois University Edwardsville Logarithms and antilogarithms are defined and developed for use in calculations.

MISC 371

Studying the Kinetics of the Solvolysis of Chloro-2-Methylpropane

Introducing Graphing Techniques

William H. Brown, Beloit College

M. L. Gillette, Indiana University Kokomo, and H. Anthony Neidig, Lebanon Valley College

The rate of chemical reaction of 2-chloro-2-methylpropane with aqueous 2-propanol is measured by determining the amount of hydrochloric acid produced. The rate data are evaluated graphically to demonstrate the dependency of the reaction rate on 2chloro-2-methylpropane concentration. (2 hrs.)

The various terms associated with graphing techniques are defined and discussed. Specific information is given for the preparation and interpretation of an x–y graph. The plotting of various nonlinear relationships, titration data, and time–temperature data is considered.

KINE 504

MISC 408

Determining the Rate Law for the Crystal Violet–Hydroxide Ion Reaction David W. Clarke, Albany College of Pharmacy The rate law is determined for the reaction of crystal violet with hydroxide ions in aqueous solution from spectrophotometric data. (1.5 hrs.)

KINE 505

Representing Data Graphically Norman E. Griswold, Nebraska Wesleyan University The basic principles of graphing and the accompanying terminology are described. Emphasis is placed on line graphs. Instructions are given for the preparation and interpretation of different types of plotted data.

MISC 457

Studying the Rate of the Reaction of Potassium Permanganate and Oxalic Acid Richard C. Bell, Lebanon Valley College, and M. L. Gillette, Indiana University Kokomo The order of the reaction of potassium permanganate and oxalic acid is determined with respect to permanganate ion and to oxalic acid concentrations. (2.5–3 hrs.)

Balancing Oxidation–Reduction Equations Using the Oxidation Number Method Marcia Gillette, Indiana University Kokomo, and H. Anthony Neidig, Lebanon Valley College Balance equations for oxidation–reduction reactions, using the oxidation number method.

KINE 508

MISC 458

Studying the Kinetics of a Chemical Reaction

Balancing Oxidation–Reduction Equations Using the Ion-Electron Method

Ralph H. Petrucci, California State University San Bernardino; Paul C. Moews, Jr., Royal Institute of Great Britian; Judith C. Foster, Bowdoin College A determination of the rate law, activation energy, and collision frequency factor for the reaction of S2O82– and I–, and of the catalytic effect of Cu(II) on the specific rate constant. (3–4 hrs.) Introductory Chemistry

50

MISCELLANEOUS


Marcia Gillette, Indiana University Kokomo, and H. Anthony Neidig, Lebanon Valley College Balance equations for oxidation–reduction reactions, using the ion-electron method.

General Chemistry

Organic Chemistry

Technology



Naming Inorganic Compounds Marcia Gillette, Indiana University Kokomo, and H. Anthony Neidig, Lebanon Valley College A systematic method for naming inorganic compounds is presented for students to apply in a series of exercises.

MISC 521

Using Statistics to Analyze Experimental Data Peter J. Krieger, Palm Beach Community College Concepts of precision and accuracy are related to deviation and error. Measurements are made on the size of beakers, the density of marbles, the volume of test tubes, and the temperature of boiling water. (2 hrs.)

MISC 468

Radioactivity Conrad L. Stanitski, University of Central Arkansas Nuclear equations are used to represent radioactive emissions and nuclear fission. Nuclear half-life is studied.

MISC 614

Writing, Interpreting, and Balancing Chemical Equations MISC 476

Interpreting and Balancing Chemical Equations M.L. Gillette, Indiana University Kokomo, and H.A. Neidig, Lebanon Valley College The interpretation of simple chemical equations is developed. Chemical equations are written and balanced in four problem sets.

M.L. Gillette, Indiana University Kokomo, and H.A. Neidig, Lebanon Valley College Students gain experience writing, interpreting, and balancing chemical equations by completing four exercise sets. Does not involve laboratory work.

MISC 629 MISC 477

Naming Inorganic Chemical Substances

Writing and Balancing Chemical Equations

M. L. Gillette, Indiana University Kokomo, and H.A. Neidig, Lebanon Valley College

M.L. Gillette, Indiana University Kokomo, and H.A. Neidig, Lebanon Valley College Overall, complete ionic, and net ionic equations are balanced. In seven problem sets, chemical formulas are written for various compounds and the solubilities of various ionic compounds are predicted.

Use a universal systematic method for naming inorganic chemical substances to derive substance names from chemical formulas, and chemical formulas from substance names.

MISC 636

Solving Stoichiometric Problems MISC 486

M. L. Gillette, Indiana University Kokomo

Dimensional Analysis

Learn and practice a systematic method for solving several types of stoichiometric problems.

S. Kay Gunter, Scottsdale, AZ, and James P. Birk, Arizona State University Dimensional analysis is used to solve general chemistry problems using clues such as units or dimensions associated with measurements.

Introducing IUPAC Nomenclature for Organic Chemical Compounds M. L. Gillette, Indiana University Kokomo

MISC 490

Using Exponential Notation and Significant Figures Norman E. Griswold, Nebraska Wesleyan University Exponential notation is reviewed and used to solve problems with and without a calculator. Rules are reviewed for determin-


NEW! MISC 639


Students are introduced to the fundamentals of the IUPAC nomenclature system for organic compounds by learning to name hydrocarbons from their structures and by drawing structures of named hydrocarbon compounds. Does not involve laboratory work.

General Chemistry

Organic Chemistry



ing significant figures. The use of significant figures in rounding off calculations and in logarithms is considered.

MISC 459

Technology

51




MISC 873, 874, 875, 876, 877

PROP 319

Introduction to Computer-Based Graphical Analysis

Preparing Soap and Determining Its Properties

M. L. Gillette, Indiana University Kokomo, H. A. Neidig, Lebanon Valley College, and J. R. Crook, Western Washington University

L.A. Whitaker, Massachusetts Institute of Technology

Exercises are presented to be solved by computer-based graphical analysis. The exercises involve the development of such linear relationships as those between pressure and volume, frequency and wavelength of light, and the transmittance of a solution and the molarity of the solution. (2.5 hrs.) MISC 873 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . LW/Win MISC 874 . . . . . . . . . . . . . . . . . . . . . . . TI-83 Graphing Calculator MISC 875 . . . . . . . . . Vernier Graphical Analysis for Windows MISC 876. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Excel for Windows MISC 877 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Excel 97

PROP 332

Evaluation of the Gas Law Constant James N. Spencer, Franklin and Marshall College The gas law constant is evaluated from pressure, volume, and temperature data obtained on a sample of H2 prepared by reaction of Mg and HCl. (2 hrs.)

PROP 344

PROPERTIES

Molar Mass Determination by Freezing-Point Depression in t-Butyl Alcohol

PROP 041

M. L. Gillette and S.R. Johnson, Indiana University Kokomo

A Study of the Molal Freezing-Point Constant of Water (Revised)

The freezing-point of t-butyl alcohol, the molal freezing-point constant for t-butyl alcohol, and the molar mass of an unknown are determined. (3 hrs.)

Ronald C. Johnson, Emory University After the molal freezing-point constant for water is evaluated, the dependence of the experimental constant on the nature of the solute and the concentration of the solute is determined. (3 hrs.)

PROP 353

Statistical Analysis of Experimental Density Data Clyde R. Metz, College of Charleston

PROP 236

Aqueous Solutions A. L. Kemppainen, Finlandia University The solubility of various molecular and ionic substances in water is observed. The effect of various factors on the solubility rate is determined. Students prepare a supersaturated solution and observe precipitation. Students also observe how water acts as a reaction medium by comparing the rate of reaction with wet and dry chemicals. (1.5–2 hrs.)

From mass–volume data obtained on glass beads, the averages, standard deviations, and confidence intervals are calculated. The density of the beads and an estimate of random error in the density are determined. (2 hrs.: advanced)

PROP 362

Evaluation of 0 K William F. Kieffer, The College of Wooster From volume—temperature data on a sample of air, the number of degrees between 0C and 0 K is determined. (3 hrs.)

PROP 240

Structure and Properties of Alcohols A. L. Kemppainen, Finlandia University Students examine molecular models of selected alcohols. Some physical and chemical properties of these alcohols are observed and related to the molecular structure of the alcohols. An unknown alcohol is identified as primary, secondary, or tertiary. (1.5 hrs.)


52

A soap is prepared from an oil and a fat. Some of the properties of soaps and detergents are determined and compared. (2.5 hrs.)


PROP 374

Separating a Binary Mixture H. Anthony Neidig, J. Iskowitz, and M. Royer, Lebanon Valley College The components of a mixture of sand and NaCl are separated. The percent composition of the mixture and the percent recov-

General Chemistry

Organic Chemistry

Technology



PROP 385

Diffusion of Gases H.A. Neidig, Lebanon Valley College, and J.N. Spencer, Franklin and Marshall College

PROP 377

Determining the Molar Volume of Oxygen John H. Bedenbaugh, Thomas S. Heard, and Angela O. Bedenbaugh, University of Southern Mississippi The molar volume of oxygen is determined from data obtained by collecting a measured volume of oxygen produced from the quantitative, yeast-catalyzed decomposition of a known amount of H2O2. This volume is related to the stoichiometry of the reaction and to the gas laws. (2–3 hrs.)

PROP 379

Determining the Proportionality Constant, R, in the Ideal Gas Equation John H. Bedenbaugh, Thomas S. Heard, and Angela O. Bedenbaugh, University of Southern Mississippi The proportionality constant in the ideal gas equation is determined by collecting a measured volume of oxygen produced from the quantitative, yeast-catalyzed decomposition of H2O2. This volume is related to the stoichiometry of the reaction and to the gas laws. (2–3 hrs.)

The relative rates of diffusion of NH3 gas and of HCl gas are determined. (2 hrs.)

PROP 391

Solutions H.A. Neidig, Lebanon Valley College, and J.N. Spencer, Franklin and Marshall College Relative solubility is determined of Na2CO3, naphthalene, and BaSO4 in water and cyclohexane. The relative miscibility is determined for 2-propanol, cyclohexane, and water in each other. The effect of particle size on the solubility of CuSO4•5H2O is determined. For a KCl solution of unknown concentration, the density, percent by mass, solubility of KCl per 100 mL of water, and the molarity of the solution are found. (2–3 hrs.)

PROP 393

Studying Density Using Salad Oil and Vinegar Wendy Audrey Reichenbach, Chemical Abstracts Service and Ohio State University

PROP 383

The intensive property density is studied by measuring and comparing the densities of oil and vinegar. (2 hrs.)

Density of Liquids and Solids H.A. Neidig, Lebanon Valley College, and J.N. Spencer, Franklin and Marshall College From the measured mass and volume of a sample of rubbing alcohol, the density of the alcohol is calculated. After the volume of a weighed rubber stopper is found by water displacement, the density of the stopper is determined. Density of an unknown metal sample is determined. (2 hrs.)

PROP 384

PROP 407

Determining the Molar Volume of Carbon Dioxide Judith A. Douville and Philip Raoul Douville, Central Connecticut State University An unknown mass of solid CO2 is vaporized in a tared flask. The mass of CO2 vapor is found and the molar volume calculated. (2 hrs.)

Charles’ Law H.A. Neidig, Lebanon Valley College, and J.N. Spencer, Franklin and Marshall College

PROP 410

Charles’s law is established by obtaining volume–temperature data for a sample of air. (2–3 hrs.)

J. N. Spencer, Franklin and Marshall College, and M. L. Gillette, Indiana University Kokomo

Studying Boyle’s Law


ery of the components are calculated. Extensive instructions are given for gravity filtration and evaporation. (2–2.5 hrs.)

The validity of Boyle’s law is tested by determining the variation in pressure of air with volume. (2 hrs.)



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PROP 412

PROP 461

Diffusion of Gases and Graham’s Law

Separating and Isolating the Components of a Ternary System


Grover W. Everett, East Carolina University, and Grover W. Everett, Jr., University of Kansas The relative rates of diffusion of two gases are determined. These relative rates are used to calculate the molar mass of one of the gases. (2 hrs.)

Differences in physical and chemical properties are used to separate the components of a mixture of benzoic acid, calcium carbonate and sand. The percent recovery is calculated. The filtrate is treated for disposal. (3 hrs.)

PROP 42

Determining the Solubility of an Unknown Salt at Various Temperatures

PROP 474

Enno Wolthuis, Calvin College

Investigating Density, Miscibility, and Solubility

The solubility of an inorganic salt in water at various temperatures is determined, and a solubility curve for the salt is drawn. (3 hrs.)

P.A. Metz, University of Georgia, and T.M. Martinez, Texas Tech University The densities of three different liquids are determined. Their mutual miscibilities are studied. The solubility of iodine in each liquid is investigated. (2 hrs.)

PROP 440

Identifying a Liquid Using Physical Properties S.J. Melford and J.A. Anysas, DePaul University Procedures to identify the physical properties of density, solubility in water and cyclohexane, and boiling point are followed using a known, then an unknown, liquid. The data are used to identify the unknown. (2–3 hrs.)

PROP 481

Determining the Molar Mass of a Volatile Liquid by the Dumas Method John W. Alcock, Quinnipiac College, and M.L. Gillette, Indiana University Kokomo The density of the vapor of an unknown volatile liquid is determined. The calculated density and the ideal gas equation are used to calculate the molar mass of the liquid. (2.5–3 hrs.)

PROP 454

Osmosis and Dialysis Gayle N. Sauer, The Citadel, and Conrad L. Stanitski, University of Central Arkansas The osmosis of water through potato cell walls is studied and evaluated. The dialysis of solutes through dialysis tubing is studied and evaluated. (2 hrs.)

PROP 495

Classifying Matter by Properties Grover W. Everett, East Carolina University and Grover W. Everett, Jr., University of Kansas

PROP 460

Chemical and physical properties of selected substances are determined. Some of these properties are used to separate mixtures of the substances. (3 hrs.)

Separating and Isolating the Components of a Binary System

PROP 500

Marcia Gillette, Indiana University Kokomo, and H. Anthony Neidig, Lebanon Valley College Differences in physical and chemical properties are used to separate the components of a mixture of calcium carbonate and sand. The percent recovery is calculated. The filtrate is treated for disposal. (2–2.5 hrs.)


54

Marcia Gillette, Indiana University Kokomo, and H. Anthony Neidig, Lebanon Valley College


Determining Molar Mass by Freezing-Point Depression George Deckey and Charles Marzzacco, Rhode Island College The molar mass of an unknown organic compound is determined from the freezing-point depression of an aqueous solution of the unknown. (3 hrs.)

General Chemistry

Organic Chemistry

Technology



PROP 518

Fats, Oils, Soaps, and Detergents

Separating and Recovering the Components of a Ternary Mixture

L. G. Wade, Jr., Whitman College Some physical and chemical properties of a saturated fat and an oil are compared. A fat is saponified to make soap. The emulsifying properties of soap and a detergent are compared. (2–2.5 hrs.)

PROP 507

Determining Molar Mass by Freezing-Point Depression in Naphthalene Daniel C. Harris, China Lake, CA The Kf of naphthalene is calculated from freezing-point data. The molar mass of an unknown is determined by measuring the freezing-point depression of a solution of the unknown in naphthalene. (3 hrs.)

PROP 513

Separating and Isolating the Major Components of Milk Peter Markow, Saint Joseph College, CT A separation scheme is followed to isolate casein, whey proteins, milk fat, and lactose from milk. Their mass percent and percent recovery are determined. A comparison can be made of the composition of the different types of milk (whole, 2% and 1%) and different brands of milk. (2.5–3 hrs.)

H. Anthony Neidig, J. Iskowitz, and M. Royer, Lebanon Valley College; and Henry D. Schreiber, Virginia Military Institute Differences in physical and chemical properties are used to separate the components in a mixture of SiO2, NaCl, and CaCO3. The mass percent of each component in the mixture as well as the percent recovery is determined. (2.5 hrs.)

PROP 522

Determining the Molar Mass of Carbon Dioxide Barbara Albers Jackson, Tennessee Technological University Samples of CO2 are collected in plastic bags. Measurement of the mass and volume of each gas sample, along with buoyancy corrections, allows the molar mass as well as the molar volume of CO2 to be calculated. (1.5 hrs.) NEW! PROP 524

Studying the Volume-Temperature Relationship of a Gas Conrad L. Stanitski, University of Central Arkansas The volume of a confined sample of air is monitored as a function of temperature at constant pressure. The temperature of absolute zero is determined by extrapolating the resulting volume-temperature plot to zero volume. (2 hrs.)

PROP 515

Using Density to Determine the Sugar Content in Commercial Beverages S. K. Henderson, C. A. Fenn, and J. D. Domijan, Quinnipiac College The densities of solutions of known sugar content are measured. The resulting graphical calibration is used to determine the mass percents sugar in fruit juices, iced teas, lemonades, and/or sodas from their densities. (2 hrs.)

NEW! PROP 530

Investigating the Intermolecular Forces Controlling Protein Folding Yvonne M. Gindt, Lafayette College and Richard C. Hartung, University of Nebraska at Kearney Phycocyanin protein is extracted from over-the-counter Spirulina capsules. Students then determine whether the protein remains folded or is unfolded in various solvents and conditions by observing its color and fluorescence. (3 hrs.)

PROP 516

Identifying a Solid by Its Density

PROP 602

H. A. Neidig, Lebanon Valley College; and Henry D. Schreiber, Virginia Military Institute

Determining Density

The density of a solid is determined graphically after measuring the mass and volume of each of several different-size samples of that solid. This density is compared to a table of densities to identify the solid. (1.5 hrs.)




PROP 506

M.L. Gillette, Indiana University Kokomo, H.A. Neidig, Lebanon Valley College, and J.N. Spencer, Franklin and Marshall College Mass and volume data are collected for a known solid, a known liquid, and for an object of unknown composition. The density General Chemistry

Organic Chemistry


Technology

55

CHEMICAL EDUCATION RESOURCES First-Year Labs Experiment Descriptions of each substance is determined from these data, and the unknown is identified from a list of possibilities. (1.5 hrs.)

Observing Some Physical and Chemical Changes in Matter

PROP 603


Resolving a Two-Component Mixture M.L. Gillette, Indiana University Kokomo, H. Anthony Neidig, J. Iskowitz, and M. Royer, Lebanon Valley College Sand and table salt are separated and recovered from a mixture of the two. Percent composition and percent recovery are calculated. (1.5 hrs.)

Grover W. Everett, East Carolina University, Grover W. Everett, Jr., University of Kansas, and M.L. Gillette, Indiana University Kokomo Some physical and chemical properties of selected substances are observed. (1.5–2 hrs.) PROP 632

Studying Charles’ Law PROP 608

Conrad L. Stanitski, University of Central Arkansas

Calculating the Molar Volume of Carbon Dioxide

Study the relationship between the volume and temperature of a confined gas sample at constant pressure. (2 hrs.)

Judith A. Douville and Philip Raoul Douville, Central Connecticut State University Mass and volume measurements of a CO2 gas sample are made at laboratory temperature and pressure. The data are used with the gas laws to calculate the molar volume of CO2 at STP. (1–1.5 hr)

PROP 615

Studying Some Aspects of Solubility M.L. Gillette, Indiana University Kokomo, H.A. Neidig, Lebanon Valley College, and J.N. Spencer, Franklin and Marshall College Relative solubility of three substances in each of two solvents is determined. Relative miscibility is determined for three pairs of liquids. The effect of crystal size on the solubility rate of a solid is observed. (1–1.5 hrs.)

PROP 621

PROP 878, 880, 882

Molar Mass Determination by Freezing-Point Depression M. L. Gillette, Indiana University Kokomo, S. R. Johnson, Indiana University Kokomo, and J. R. Crook, Western Washington University The temperature probe is calibrated and the system is used to collect temperature–time data for the determination of the freezing-point of t-butyl alcohol; of a solution of salicylic acid in t-butyl alcohol; and of a solution of an unknown in t-butyl alcohol. From these data, the Kf of t-butyl alcohol, the molality of the unknown solution, and the molar mass of the unknown are calculated. (2.5–3 hrs.) PROP 878 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . CBL PROP 880 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . LW/Win PROP 882 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Vernier LP

Isolating the Components of a Three-Component Mixture

REACTIONS

H.A. Neidig, J. Iskowitz, and M. Royer, Lebanon Valley College, and M.L. Gillette, Indiana University Kokomo The components of a mixture of sand, sodium chloride, and calcium carbonate are separated. Students calculate the percent, by mass, of each component in the original mixture, and the percent recovery of all components. (2 hrs.)


56

PROP 627


REAC 321

Determining the Effects of Acid Rain Kenneth E. Borst, Rhode Island College The alkalinities of natural water samples are determined by titration with a standardized solution of H2SO4. The end points of the titrations are determined with a pH meter or with a number of indicators. The sampled stream or lake will then be classified from the value of the alkalinity. (3 hrs.)

General Chemistry

Organic Chemistry

Technology



Single Replacement Reactions and Relative Reactivity H.A. Neidig, Lebanon Valley College, and J.N. Spencer, Franklin and Marshall College The relative reactivity of Al, Fe, and Cu is determined by their reaction with dilute HCl and with solutions of the corresponding salts. These data are used as a basis for emphasizing the writing of chemical equations. (2 hrs.)

REAC 390

Double Replacement Reactions H.A. Neidig, Lebanon Valley College, and J.N. Spencer, Franklin and Marshall College From laboratory observations taken when two different solutions are mixed, a prediction is made as to whether or not a reaction occurred. These data are used as a basis for emphasizing the writing of chemical equations. (2 hrs.)

solubility of any precipitate in acetic acid. Chemical equations describing the observed reactions are written after bench work is completed. (2–2.5 hrs.)

REAC 413

Preparing and Studying Oxygen and Some of Its Compounds Grover W. Everett, East Carolina University, and Grover W. Everett, Jr., University of Kansas Oxygen gas is prepared by the decomposition of hydrogen peroxide, using tetraammine-copper(II) ion as a catalyst. The action of oxygen on burning sulfur, burning phosphorus, glowing steel wool, and glowing charcoal is determined. Several metal oxides are heated to test their relative stabilities. (2 hrs.) REAC 414

Determining the Comparative Reactivities of Several Metals M. L. Gillette, Indiana University Kokomo, and H. A. Neidig, Lebanon Valley College

REAC 399

Detecting Signs of Chemical Change M. L. Gillette, Indiana University Kokomo, and H. A. Neidig, Lebanon Valley College

The comparative reactivities of a group of metals are determined from their reactions with hydrochloric acid solution and with solutions of metallic salts. (2 hrs.)

Combinations of liquids, solutions, and solids are mixed. From laboratory observations, chemical changes are determined. (2 hrs.)

REAC 444

REAC 405

Elva Mae Nicholson and O. Bertrand Ramsey, Eastern Michigan University

Identifying Six Solutions by their Interactions H. Anthony Neidig and J. Iskowitz, Lebanon Valley College, and M.L. Gillette, Indiana University Kokomo Students write equations for reactions between pairs of six dissolved compounds assigned prior to the laboratory period. Known pairs from these solutions are mixed and observed. Then unknown pairs of the six are mixed and identified from the data. (2 hrs.)

Estimating the Optimum pH and Temperature for Digestive Enzyme Activity

The activities of the digestive enzymes pepsin, pancreatin, and salivary amylase mixed with foods are observed under various pH and temperature conditions. (2.5 hrs.)

REAC 446

Qualitative Testing for Carbohydrates James O. Schreck, University of Northern Colorado, and William M. Loffredo, East Stroudsburg University

REAC 406

Writing Chemical Equations and Identifying Unknown Solutions Using Microscale Techniques

Seven known saccharides, and then an unknown, are identified by product color after exposure to dehydrating and to oxidizing reagents. (2.5–3 hrs.)


REAC 389

M.L. Gillette, Indiana University Kokomo, and H. A. Neidig, Lebanon Valley College Six unknown solutions are identified from a systematic study of the interactions of the ions in solution with each other and the



General Chemistry

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57

CHEMICAL EDUCATION RESOURCES First-Year Labs Experiment Descriptions matic compounds. Seven known and two unknown compounds are tested for unsaturation. (1.5–2 hrs.)

REAC 447

Qualitative Testing for Lipids


Frank R. Milio, Towson State University, and William M. Loffredo, East Stroudsburg University Types of lipids are identified and classified using physical and chemical properties. Tests employed include grease spot, solubility, emulsification, saponification, unsaturated lipid halogenation, Leibermann–Burchard cholesterol, and ammonium molybdate for phosphorus. (2.5–3 hrs.)

REAC 448

Qualitative Tests for Amino Acids and Proteins

A Sequence of Chemical Reactions: Transforming Copper Guy B. Homman, Emporia State University, and M.L. Gillette, Indiana University Kokomo A sequence of chemical transformations are performed, starting and ending with metallic copper. The percent copper recovered is determined. REAC 480 differs from REAC 482 in that the procedure does not involve use of a centrifuge, and zinc is used to displace copper in the last reaction. (2.5–3 hrs.)

Frank Milio, Towson State University, and William Loffredo, East Stroudsburg University The properties and reactions of amino acids and proteins are studied with reagents used to classify and identify them. (2.5–3 hrs.)

REAC 482

Copper from Start to Finish: A Sequence of Chemical Reactions Guy B. Homman, Emporia State University, Barton Houseman, Goucher College, and M.L. Gillette, Indiana University Kokomo

REAC 456

Studying Oxidation–Reduction Reactions Marcia Gillette, Indiana University Kokomo, and H. Anthony Neidig, Lebanon Valley College Several oxidation–reduction reactions are observed. Descriptions of reactants and products are recorded. The electron transfers occurring during specific redox reactions are determined and conlusions drawn about the relative strengths of some oxidizing agents. (2–2.5 hrs.)

A series of chemical transformations are carried out, beginning and ending with pure metallic copper. The mass percent recovery of copper metal is determined. REAC 482 differs from REAC 480 in that the procedure involves use of a centrifuge, and magnesium is used to displace copper in the last reaction. (2–2.5 hrs.)

REAC 502

REAC 469

Establishing the Relative Reactivity of Halogens and Halide Ions

Qualitative Tests for the OH Group in Organic Compounds

M. L. Gillette, Indiana University Kokomo, and H. A. Neidig, Lebanon Valley College

James O. Schreck, University of Northern Colorado, and Robert Silberman, SUNY, Cortland

Observations are made of some reactions involving three halogens and their corresponding ions and used to determine the relative reactivity of these species. The halide ion present in an unknown solution is identified. (2.5 hrs.)

Alcohols, phenols, and carboxylic acids are differentiated by using their acid–base and solubility properties. Ceric(IV) nitrate solution, chromic acid, and iron(III) chloride solution are used as qualitative tests for alcohols and phenols. Unknowns will be characterized as alcohols, phenols, or acids. (2 hrs.)

NEW! REAC 539

Writing Chemical Equations Based on Observation of Reactions

REAC 472

M.L. Gillette, Indiana University Kokomo, and H. Anthony Neidig, Lebanon Valley College

Qualitative Tests for Alkenes Robert Silberman, SUNY Cortland Pyridinium bromide perbromide and potassium permanganate solutions are used to distinguish alkenes from alkanes and aro-


58

REAC 480


Several chemical reactions are performed, and their products identified. Reactions are described by writing their chemical equations, complete ionic equations, and net ionic equations.

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REAC 626

Observing Some Oxidation–Reduction Reactions M.L. Gillette, Indiana University Kokomo, and H.A. Neidig, Lebanon Valley College

REAC 604

Observing Signs of Chemical Reaction M.L. Gillette, Indiana University Kokomo, and H. Anthony Neidig, Lebanon Valley College Evidence for chemical change is identified from observations of the physical characteristics of solids, liquids, and solutions, before and after mixing. (1.5–2 hrs.)

Several oxidation–reduction reactions are observed. Students identify the oxidizing and reducing agents in the reactions. (1.5 hrs.)

REAC 634

Identifying Solutions of Ionic Compounds H. A. Neidig and J. Iskowitz, Lebanon Valley College, and M. L. Gillette, Indiana University Kokomo

REAC 610

Observing Single Replacement Reactions M.L. Gillette, Indiana University Kokomo, H.A. Neidig, Lebanon Valley College, and J.N. Spencer, Franklin and Marshall College Various pairs of Al, Fe, and Cu are combined with solutions of their salts, and each metal is reacted with 6M HCl. The relative reactivities of these metals and H2 are determined from experimental observations. (1–1.5 hrs.)

Identify the ionic compound present in each of four unknown solutions by systematically studying the interactions among solutions of known composition, and then among the unknown solutions. Write chemical equations describing the observed reactions. (1.5 hrs.)

REAC 635

Discovering Some Periodic Properties of Elements John Woolcock, Indiana University of Pennsylvania, and M. L. Gillette, Indiana University Kokomo

REAC 611

Observing Double Replacement Reactions M.L. Gillette, Indiana University Kokomo, H.A. Neidig, Lebanon Valley College, and J.N. Spencer, Franklin and Marshall College Six combinations of two aqueous solutions are mixed and observed to determine if reactions occur. Solubility data are used to write chemical equations to describe these observations. (1–1.5 hrs.)

Discover the relationship between certain kinds of chemical reactivities of some elements and their relative positions on the periodic table. (1.5 hrs.)

NEW! REAC 908

Identifying Solutions by Observing Chemical Reactions Patricia A. Metz, University of Georgia

REAC 613

Classifying Some Chemical Reactions M.L. Gillette, Indiana University Kokomo, and H.A. Neidig, Lebanon Valley College Students perform several chemical reactions. From observations, students write chemical equations for the reactions, and classify each reaction as one of four general types: combination, decomposition, single displacement, or double displacement. (1.5 hrs.)



Predict whether a reaction will occur for each pair of eight ionic solutions. Given seven of the eight solutions as unknowns, combine pairs of solutions and observe results. Identify the unknown solutions. (2 hrs.) SCENARIO: Enviro Safe, Inc. received from the Biology Department seven, five-gallon carboys of solutions labeled Experiment 9. If the solutions are not identified, Enviro Safe will charge substantially more to dispose of them. The Biology Department knows eight solutions were used in the experiment, but it needs help determining which are in the carboys and which is missing. Students write a memo to Enviro Safe detailing their analysis.

General Chemistry

Organic Chemistry



Reactions are classified as combination, decomposition, singledisplacement, or double- displacement. (2 hrs.)

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STOICHIOMETRY

Determining the Empirical Formula of Copper Chloride


STOI 003

Stoichiometry of the Lead(II) Nitrate—Potassium Halide—Water System

Don Stafford, East Central University

By use of Job’s method, gravimetric data are obtained for lead(II) nitrate–potassium halides systems to determine the stoichiometry of each system. (3 hrs.)

The mass of Cu formed when Zn reacts with a known amount of copper chloride solution is determined. From these data, the percent copper and chlorine in copper chloride are calculated and used to identify the empirical formula of copper chloride. After writing the stoichiometric equation for the reaction, the theoretical and percent yields of Cu are calculated. (2.5–3 hrs.)

STOI 007

STOI 388

Stoichiometry: Mole Ratio Study

The Empirical Formula of an Oxide

H.A. Neidig, Lebanon Valley College

H.A. Neidig, Lebanon Valley College, and J.N. Spencer, Franklin and Marshall College

H.A. Neidig, Lebanon Valley College

The stoichiometry of the Pb(NO3)2–KI system is found gravimetrically by using a mole ratio experimental design. (2 hrs.)

From gravimetric data, the empirical formula of an oxide of magnesium is determined. (2 hrs.)

STOI 301

Determination of the Formula of a Chemical Compound David P. Dingledy, SUNY College, Fredonia The empirical formula of a compound containing Pb and S is determined from gravimetric analysis. (1.5 hrs.)

STOI 315

STOI 398

Determining the Empirical Formula of a Compound Containing Magnesium and Oxygen Nancy L. Suttles, Purdue University Magnesium and oxygen are combined and the product is dissolved in hydrochloric acid and heated. The resulting oxide of magnesium is massed and the empirical formula of this compound is determined. (3 hrs.)

Synthesis of Lead(II) Chromate H.A. Neidig, Lebanon Valley College

STOI 401

The percent yield of PbCrO4 from the reaction of a solution of K2CrO4 and a solution of Pb(NO3)2 is determined. Extensive instructions are given for gravity and vacuum filtration. (2.5 hrs.)

Studying the Stoichiometry of the Reaction of Nickel(II) Ion and Hydroxide Ion Using Microscale Techniques M.L. Gillette, Indiana University Kokomo, and H. Anthony Neidig, Lebanon Valley College

STOI 369

The Reaction of Magnesium with Hydrochloric Acid H.A. Neidig, Lebanon Valley College, and J.N. Spencer, Franklin and Marshall College

The stoichiometric relationship between nickel(II) and hydroxide ions is studied for the reaction of nickel(II) nitrate solution and sodium hydroxide solution. The method of continuous variations and the mole-ratio method are used for this experiment. (2 hrs.)

A weighed sample of Mg reacts with HCl solution and the released H2 is measured. From the experimental data, the stoichiometric equation for the reaction is determined. (2 hrs.)


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STOI 386


General Chemistry

Organic Chemistry

Technology



STOI 496

Precipitating Lead Chromate on a Small Scale

Approximating Avogadro’s Number Using Glass Beads and Monomolecular Film

H.A. Neidig, Lebanon Valley College and J. N. Spencer, Franklin and Marshall College The theoretical, actual, and percent yields of lead chromate formed from the reaction of solutions of potassium chromate and lead nitrate. Extensive information is included on filtration and the handling of precipitates and residues. (2.5 hrs.)

Don McMasters, Indiana University, and M. L. Gillette, Indiana University Kokomo Avogadro’s number is approximated from measurements made on a collection of glass beads and a film of oleic acid on water. (2 hrs.)

STOI 423

STOI 497

Determining the Empirical Formula of a Compound

Reacting Vinegar with Baking Soda

David P. Dingledy, SUNY College, Fredonia

The mass and density of a known volume of household vinegar is determined. The volume of vinegar required to completely react a known mass of baking soda is determined. The mass percent acetic acid in the vinegar is calculated and compared to the labeled percent acetic acid. The percent error is found. (2–3 hrs.)

The empirical formula of a compound is established from the gravimetric determination of the molar ratio of the reacting masses of oxygen and magnesium. (2 hrs.)

Henry D. Schreiber, Virginia Military Institute

STOI 438

Determining the Formula and Estimating the Dissociation Constant of a Complex Ion Kenneth N. Carter, Presbyterian College Reaction mixtures of silver nitrate and excess ammonia produce a silver–ammonia complex ion. Mixtures are titrated to precipitation with potassium bromide solution. Titration data are used to calculate the theoretical solubility product constant (Ksp) of silver bromide, to estimate the dissociation constant (Kd) of the complex ion, and to determine n in the complex ion formula. Reaction mixtures are processed by the students for disposal. (3 hrs.: advanced)

STOI 509

Determining the Formulas of Copper(II)Ethylenediamine Complex Ions by Spectrophotometry Emily P. Dudek, Brandeis University The method of continuous variation is used with spectrophotometry to determine the molar ratio of Cu(II) to ethylenediamine. (2.5–3 hrs.: advanced)

STOI 514

Calculating Avogadro’s Number by Comparing Atoms and Oranges

STOI 475

Determining the Composition of a Cobalt(II) Nitrate Sample by Visible Spectrophotometry Henry D. Schreiber, Virginia Military Institute A spectrophotometric procedure is developed to analyze aqueous solutions for cobalt. This procedure is used to determine the mass percent cobalt in an unknown cobalt nitrate sample and to establish the cobalt nitrate sample’s molecular formula. (1.5–2 hrs.)

Henry D. Schreiber, Virginia Military Institute The efficiency of spheres randomly packed into containers is measured. The maximum packing efficiency of these randomly packed spheres is determined. From these data, Avogadro’s number is calculated and the percent error is determined. (1.5 hrs.)

STOI 520

Determining the Empirical Formula of Magnesium Oxide


STOI 420

Henry D. Schreiber, Virginia Military Institute; H. A. Neidig, Lebanon Valley College; and James N. Spencer, Franklin and Marshall College Magnesium oxide is synthesized by heating magnesium metal in



General Chemistry

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CHEMICAL EDUCATION RESOURCES First-Year Labs Experiment Descriptions air. The empirical formula of this compound is determined from the mass of oxygen that combines with magnesium. (2 hrs.)

Determining the Stoichiometry of a Double Displacement Reaction


NEW! STOI 525

M. L. Gillette, Indiana University Kokomo

Determining the Empirical Formula of Zinc Chloride M. L. Gillette, Indiana University Kokomo A solution of zinc chloride is prepared, and its zinc content analyzed by a complexometric titration with EDTA. The empirical formula is then determined for zinc chloride. (1.5 hrs.)

The stoichiometry of the reaction of iron(III) chloride and sodium hydroxide is determined by mixing various molar ratios of the two reagents and determining the identity of any reagent present in excess. (1.5 hrs.)

STOI 903

Determining Reaction Stoichiometry by Continuous Variations

STOI 606

Determining the Empirical Formula of Magnesium Oxide M.L. Gillette, Indiana University Kokomo, H.A. Neidig, Lebanon Valley College, and J.N. Spencer, Franklin and Marshall College

Patricia A. Metz, University of Georgia The reaction stoichiometry of sodium thiosulfate and sodium hypochlorite is determined using the method of continuous variations. (2.5–3 hrs.)

STOI 607

SCENARIO:Scenario: A city sanitation worker receives second-degree burns when bottles of chemicals in a dumpster he is emptying break and cause an exothermic chemical reaction. The city forensics laboratory requests assistance determining the stoichiometric ratio of the chemicals involved. Students write a report of their investigation for the director of the forensics laboratory.

Reacting Vinegar with Baking Soda to Find Percent Acetic Acid

STOI 906

A measured mass of Mg is oxidized, and the mass of the product is compared to the mass of Mg. From these data, the empirical formula of magnesium oxide is determined. (1–1.5 hrs.)

Henry D. Schreiber, Virginia Military Institute, and M.L. Gillette, Indiana University Kokomo The percent acetic acid in household vinegar is determined by reacting it with baking soda. (1–1.5 hrs.)

Determining Hydrogen Peroxide Content by Gas Stoichiometry Patricia A. Metz, United States Naval Academy The molarity and mass percent of hydrogen peroxide in a solution are determined by decomposing the hydrogen peroxide and measuring the oxygen produced. (2 hrs.)

STOI 633

Determining the Empirical Formula of a Compound Containing Copper and Chlorine M. L. Gillette, Indiana University Kokomo, and Don Stafford, East Central University, OK Determine the empirical formula of a compound containing copper and chlorine by reacting a measured volume of a solution of the compound with zinc, and weighing the Cu produced. (1.5–2 hrs.)


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NEW! STOI 637


SCENARIO: Scenario: A plant worker, fired by his previous employer for making a dilution calculation error, has made a similar mistake at his new job with Global Hydrogen Peroxide. Assistance is needed determining the concentration of a batch of over-diluted swimming pool shocker to see if it can be salvaged as household hydrogen peroxide. Students write a calculation protocol for diluting any hydrogen peroxide solution to a specific concentration.

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Technology



STRC 435

STRC 345

Chemical Models: Ball-and-Stick Models of Organic Compounds

The Visible Atomic Spectrum of Hydrogen


M. L. Gillette and S. R. Johnson, Indiana University Kokomo A calibration curve for a Bunsen spectroscope is prepared using a discharge tube. The scale readings are determined for the four visible lines of hydrogen, using a hydrogen discharge tube. E and n2 are calculated for each of the visible emission lines of hydrogen. (2 hrs.)

Models of some organic molecules are constructed using a process of writing Lewis structures and structural formulas, then assembling ball-and-stick models. Based on these models, figures may be drawn and products of reactions predicted. (1.5 hrs.)

STRC 449

Determining Atomic Emission by Spectroscopy

STRC 351

Models and the Crystalline State Clyde R. Metz, College of Charleston Models of simple cells are constructed to gain insight into the spatial arrangements of atoms, ions, and molecules in crystals; the models are analyzed for values of unit cell, coordination number, radius ratio, percent volume occupied, and density. (2 hrs.)

Patricia A. Metz, University of Georgia Atomic emission spectra produced by gas discharge tubes and flame tests are examined, using an inexpensive, hand-held spectroscope. Data collected are used to calculate the Rydberg constant mathematically and graphically. (2 hrs.)

STRC 467

Structural and cis-trans Isomerism in Carbon Compounds

STRC 409

Molecular Geometry and Bonding Clyde Metz, College of Charleston The spatial relationships of atoms within molecules and ions are studied by construction and examination of appropriate models. Considerations involve both the VSEPR and valence bond theories. (3 hrs.)

Conrad L. Stanitski, University of Central Arkansas Molecular structures and models are used to examine structural and cis-trans isomerism in carbon compounds, especially hydrocarbons. (1.5–2 hrs)

STRC 473

STRC 434

Molecular Structure and Optical Isomerism in Carbon Compounds

Writing Lewis Symbols and Lewis Structures

Robert Silberman, SUNY Cortland


Molecular models, drawings, and templates are used to examine optical isomerism in carbon compounds with one or two chiral centers. (1.5–2 hrs.)

Lewis symbols and structures are developed for elements, ions, compounds, and equations. Empirical formulas are predicted. (1.5 hrs.)

STRC 631

Visualizing Chemical Structures Using Lewis Models M. L. Gillette, Indiana University Kokomo, and H. A. Neidig, Lebanon Valley College, and J. N. Spencer, Franklin and Marshall College


STRUCTURE

Write Lewis symbols for elements and monoatomic ions. Write Lewis structures for covalent compounds and polyatomic ions.



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SYNTHESIS


SYNT 095

SYNT 433

Preparation and Analysis of a Coordination Compound Clifford J. Creswell, Hamline University A coordination compound containing cobalt, chlorine, and ammonia is synthesized. The formula of the compound is determined by gravimetric analysis for chloride, and spectrophotometric analysis for cobalt. (9 hrs.: advanced)

SYNT 341

Synthesizing and Analyzing a Coordination Compound of Nickel(II) Ion, Ammonia, and Chloride Ion George S. Patterson, Suffolk University, MA A coordination compound is synthesized from the reaction of nickel(II) chloride hexahydrate and ammonia. Mass percent of ammonia in the product is determined by back titration and that of nickel ion by spectrophotometry. Empirical formula and percent yield are calculated. (9 hrs.)

Synthesis of Strontium Iodate Monohydrate H.A. Neidig, J. Iskowitz, K.D. Henry, and M. Royer, Lebanon Valley College Strontium iodate monohydrate is synthesized from solutions of Sr(NO3)2 and KIO3. Using the limiting reagent, the percent yield of product is calculated. Extensive instructions are given for gravity and vacuum filtration. (2 hrs.)

SYNT 439

Synthesizing Aspirin Robert L. Glogovsky, Elmhurst College Acetylsalicylic acid is synthesized from salicylic acid and acid anhydride. The product is tested for phenolic groups and ester formation. The reaction mixture is processed by the students for disposal. (3 hrs.)

SYNT 347

Preparation of Strontium Iodate Monohydrate

SYNT 451

H.A. Neidig, J. Iskowitz, K.D. Henry, and M. Royer, Lebanon Valley College

Synthesizing Alum

From solutions of Sr(NO3)2 and KIO3, Sr(IO3)2·H2O is prepared. The percent yield of product is calculated. Extensive instructions are given for gravity and vacuum filtration. (2 hrs.)

Marcia Gillette, Indiana University Kokomo, and H. Anthony Neidig, Lebanon Valley College Alum is synthesized from an aluminum can. (2.5 hrs.)

SYNT 431

SYNT 452

Preparing Tris(2,4-Pentanedionato) Iron(III), an Iron Coordination Complex

Synthesizing Alum and Observing Some Chemistry of Aluminum

George S. Patterson, Suffolk University

Marcia Gillette, Indiana University Kokomo, and H. Anthony Neidig, Lebanon Valley College

Tris(2,4-pentanedionato)iron(III) is prepared from iron(III) chloride hexahydrate and 2,4-pentadione in methanol and precipitated with water. Crystals are weighed to determine the percent yield. (3 hrs.)

Alum is synthesized from an aluminum can. Some reactions of aluminum and some of its compounds are observed. (2.5 hrs.)

SYNT 470 SYNT 432

Preparing Tetraaminecopper(II) Sulfate Monohydrate Philip J. Squattrito, Central Michigan University A reaction of copper(II) sulfate pentahydrate and ammonia in aqueous solution is used to produce tetraaminocopper(II) sul-


64

fate. The product is isolated from solution by adding ethanol and cooling. The percent yield is determined. (2 hrs.)


Preparation of Esters Conrad L. Stanitski, University of Central Arkansas Organic acids and alcohols are used to prepare several esters. These esters are characterized by their odor, and the odors are used to identify an unknown ester. (1.5–2 hrs.)

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Organic Chemistry

Technology



Isolating Caffeine from Tea Robert Silberman, SUNY Cortland, and William Loffredo, East Stroudsburg University Caffeine is extracted from instant tea and is purified by sublimation. The mass percent of caffeine in the instant tea is determined. (2–2.5 hrs.)

TECHNIQUES

TECH 231

Isolation (by Crystallization) and Identification of a Component of a Drug Mixture

NEW! SYNT 540

Synthesizing Alum and Determining Chemical Properties of Aluminum and Alum M.L. Gillette, Indiana University Kokomo, and H. Anthony Neidig, Lebanon Valley College Alum is synthesized from aluminum foil, with percentage yield determined. Several reactions are performed in order to compare selected chemical properties of aluminum with those of iron. (2.5 hrs.)

Karen P. Long, Diablo Valley College Water is used to extract a component from an antacid analgesic preparation. After recrystallization, the isolated compound is identified by its melting point. (2 hrs. without recrystallization; 3 hrs. with recrystallization and melting point.)

TECH 233

Melting Points of Organic Compounds Karen P. Long, Diablo Valley College

SYNT 612

Preparing Alum M.L. Gillette, Indiana University Kokomo, and H.A. Neidig, Lebanon Valley College Alum is prepared from aluminum foil. Students calculate the theoretical and percent yield for their preparation. (2 hrs.)

The melting points of analgesic and antipyretic formulations such as phenacetin, acetaminophen, and tartaric acid are determined. The effect of the melting point of an added impurity is determined. An unknown is identified on the basis of its melting point. (1–2 hrs.)

NEW! TECH 244

Recrystallizing Salicylic Acid and Determining Its Purity

SYNT 628

Preparing Aspirin M.L. Gillette, Indiana University Kokomo, and Robert L. Glogovsky, Elmhurst College Acetylsalicylic acid (aspirin) is prepared from salicylic acid and acetic anhydride. Students determine the theoretical, actual, and percent yields of the preparation. (1.5 hrs.)

L. M. Divis, Franciscan University of Steubenville Salicylic acid is isolated from an impure mixture by recrystallization. Percent recovery is calculated. Procedure uses melting point technique to characterize crystal product purity. (1.5–2 hrs.)

TECH 316 SYNT 907

Filtration

Applying the Concept of a Limiting Reactant to the Synthesis of Aspirin


Patricia A. Metz, United States Naval Academy

Provides instruction in filtering techniques. Precipitates of BaSO4 and CaCO3 are formed and isolated. (2 hrs.)

The most cost-effective limiting reactant for the synthesis of aspirin is determined. A sample of aspirin is synthesized and its percent purity is determined. (3 hrs.) SCENARIO: A college marketing course is working with Atkinson Health Products to explore the feasibility of adding aspirin to its product line. As part of this study, a



General Chemistry

Organic Chemistry



small amount of aspirin must be synthesized and its yield, purity, and cost of reactants determined. Students write a memorandum outlining their findings.

SYNT 471

Technology

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TECH 363

TECH 485

Qualitative Inorganic Analysis Techniques

Measuring Mass



A discussion of laboratory techniques applicable to inorganic analysis, including formation of precipitates, centrifugation, evaporation of solutions, transfer and mixing of reagents, and preparation of supplementary equipment such as stirring rods and capillary pipets.

Practice in caring for and using triple-beam, top-loading, and analytical balances to measure sample masses. (1–2 hrs.)

TECH 380

Making and Using Visible Absorption Measurements

Safety Practices in the Chemistry Laboratory

Norman E. Griswold, Nebraska Wesleyan University, and M. L. Gillette, Indiana University Kokomo

H.A. Neidig, Lebanon Valley College, and J.N. Spencer, Franklin and Marshall College An overview of laboratory safety practices, including a discussion of material safety data sheets, suggestions for actions in case of laboratory accidents, a page to record safety equipment locations, a chemical laboratory safety agreement, and a laboratory safety quiz.

An introduction to the use of spectrophotometers. A spectrophotometer is used to obtain the visible spectrum of an absorbing species. After determining the analytical wavelength, absorbance data are collected and used to prepare a Beer’s law plot. The concentration is determined of an absorbing species in a solution. (3 hrs.)

TECH 489 TECH 381

The Gas Burner and Glass Working H.A. Neidig, Lebanon Valley College, and J.N. Spencer, Franklin and Marshall College The operation of a burner is discussed, and a brief exercise is included. Procedures and bench work are given for cutting, firepolishing, and bending glass tubing, drawing dropper tips, and inserting glass tubing into rubber stoppers. (2 hrs.)

Using a pH Meter Norman E. Griswold, Nebraska Wesleyan University, and M. L. Gillette, Indiana University Kokomo A discussion of the nature and use of pH meters. Information is given for standardizing a pH meter, determining the pH of a solution, and monitoring pH changes during an acid–base titration. (1 hr.)

TECH 511 TECH 382

Transfer and Measurement of Chemicals H.A. Neidig, Lebanon Valley College, and J.N. Spencer, Franklin and Marshall College

Laboratory Techniques: Measuring the Volume of Liquids Norman E. Griswold, Nebraska Wesleyan University

Transfer of chemicals and procedures for the measurement of the mass and volume of chemicals are discussed. Brief laboratory procedures are included. (2 hrs.)

The fundamental techniques and equipment used in volume measurement are discussed. Students clean and handle volumetric ware to measure volumes, prepare solutions in a volumetric flask, and use a buret for titrations. (2 hrs.)

TECH 430

TECH 600

Safety Precautions

Practicing Safety in the Chemistry Laboratory

Norman E. Griswold, Nebraska Wesleyan University A discussion of laboratory safety rules, including general laboratory techniques and handling of chemicals. A safety agreement to be signed by the student and a safety quiz are included.


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TECH 488


M.L. Gillette, Indiana University Kokomo, H.A. Neidig, Lebanon Valley College, and J.N. Spencer, Franklin and Marshall College Behaviors that promote safety in the laboratory are described. Includes a discussion of Material Safety Data Sheets, a laborato-

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Technology


CHEMICAL EDUCATION RESOURCES Organic Chemistry Labs Experiment Descriptions

THER 346

Enthalpy of Neutralization H.A. Neidig, Lebanon Valley College

TECH 601

Introducing Mass and Volume Measurements

From experimental data, Hneut is calculated for the reaction of aqueous NaOH with HCl, H2SO4, and H3PO4. (3 hrs.)


THER 368

Procedures for the measurement of mass and volume and for the transfer of liquids and solids are practiced in brief bench activities. (1–1.5 hrs.)

THERMODYNAMICS

Heat of Neutralization H.A. Neidig, Lebanon Valley College, and J.N. Spencer, Franklin and Marshall College The heat of neutralization is determined for the reaction of NaOH solution and HCl solution. (2 hrs.)

THER 370

THER 074

Heat of Reaction of Magnesium and Hydrochloric Acid Carl H. Brubaker, Jr. and Richard H. Schwendeman, Michigan State University; Donald A. McQuarrie, University of California, Davis The enthalpy change for the reaction between Mg and HCl is determined by ice calorimetry. The amount of ice melted from the heat of the reaction is found by determining the decrease in volume of an ice–water mixture. (3 hrs.)

Enthalpy of Hydration H.A. Neidig, Lebanon Valley College From experimental data, the Hsoln of MgSO4 and of MgSO4•7H2O are calculated and used to calculate Hhydrn of MgSO4. (2 hrs.)

THER 428

Estimating the Calorie Content of Nuts Peter G. Markow, St. Joseph College, CT

THER 185

Enthalpy of Formation of Ammonium Salts Philip H. Rieger, Brown University, and H.A. Neidig, Lebanon Valley College The Hf o of several ammonium salts is calculated from experimental and literature data. SI units are used in this module. (6 hrs.: advanced)

The connection between food calories and chemical calories is determined by estimating the calorie content of peanuts, walnuts, and other nuts using a simple calorimeter. (2–3 hrs.)

THER 512

The Thermodynamics of KNO3 Dissolving in Water Robert Silberman, SUNY Cortland The solubility of KNO3 in water at several temperatures is measured and is used to calculate Ksp, G, S, and H for the dissolution of KNO3 in water. (1.5–2 hrs.)

THER 303

Enthalpy of Formation H.A. Neidig, Lebanon Valley College The Hf of NH4Cl, NH4NO3, and (NH4)2SO4 is calculated from the experimentally calculated Hneut of NH3 and its corresponding acid, the experimentally calculated Hsoln of ammonium salt, and literature data. (6 hrs.: advanced)

NEW! THER 529

Determining the Thermodynamics of Ca(OH)2 Solubility in Water


ry safety agreement to be signed by the student, and a laboratory safety quiz. No laboratory work is involved.

William B. Euler and Louis J. Kirschenbaum and Ben Ruekberg, University of Rhode Island The molar solubility of Ca(OH)2 in water is measured at two temperatures. Titrations with standard HCl are used to analyze



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67

CHEMICAL EDUCATION RESOURCES First-Year Labs Experiment Descriptions samples of the saturated solutions. From the calculated Ksp and Go at the two temperatures, the student determines the H o and S o for the solution of Ca(OH)2 in water. (2.5 hrs.)


Heat of Neutralization H. A. Neidig, Lebanon Valley College, J. N. Spencer, Franklin and Marshall College, and, J. R. Crook, Western Washington University

THER 609

Estimating a Heat of Neutralization

Heat of neutralization is estimated for the reaction of HCl and NaOH by plotting temperature–time data collected for measured volumes of solutions of the two compounds, before and after mixing. (1–1.5 hrs.)

The temperature probe is calibrated using two portions of water, each at a different temperature, and the system is used to obtain temperature– time data for the reaction of a NaOH solution with a HCl solution. These data are used to calculate the Hneut for the reaction. (2–2.5 hrs.) THER 883. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . CBL THER 885 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . LW/Win THER 887 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Vernier LP

THER 623

THER 901

Estimating the Calorie Content of Peanuts

Temperature Change, Heat of Reaction, and Enthalpy Change of Neutralization Reactions


Peter Markow, Saint Joseph College, and M.L. Gillette, Indiana University Kokomo The Calorie content of peanuts is estimated using a simple calorimeter. (1.5 hrs.)

THER 630

Estimating the Heat of Decomposition of Hydrogen Peroxide Charles J. Marzzacco, Rhode Island College Use temperature–time measurements to estimate the heat of decomposition of the iron(III) nitrate-catalyzed decomposition of hydrogen peroxide. (1.5 hrs.)

Patricia A. Metz, University of Georgia The temperature change, heat of reaction, and enthalpy change for an acid–base reaction are determined. The effect of varying the volume and concentration of acid and/or base and of using sulfuric acid rather than hydrochloric acid is determined. (2.5–3 hrs.) SCENARIO: Students have been asked to investigate whether or not the HAZMAT team at HighTech Electronics used an acceptable procedure to neutralize a muriatic acid spill that occurred when a tanker truck valve ruptured. Based on their investigation, the students must write a letter to the HAZMAT team supervisor supporting or attacking the procedure used.

THER 860, 862, 864

Determining Enthalpy of Neutralization H. A. Neidig, Lebanon Valley College, and J. R. Crook, Western Washington University After the temperature probe is calibrated, the system is used to collect temperature–time data for the reaction of HCl, H2SO4, and H3PO4 with NaOH solution and used to calculate Hneut. (2.5 hrs.) THER 860. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . CBL THER 862 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . LW/Win THER 864 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Vernier LP


68

THER 883, 885, 887


General Chemistry

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Technology



ANALYSIS

ANAL 727

Classifying an Unknown Compound by Functional Group Jan William Simek, California Polytechnic University Solubility tests and classification tests are used to identify organic functional groups of solid and liquid unknown compounds. (2–3 hrs.)

ANAL 751

Enantiomeric Purity of Commercial Ibuprofen A. T. Rowland, Gettysburg College Ibuprofen is isolated and purified from commercial preparations. Products are analyzed to determine if the preparations contain a racemic mixture or a pure enantiomer. Determinations are made using melting points and specific rotation. (2 hrs.)

NEW! ANAL 756

Determining the Alcohol Content of Beer and Wine Leonidas J. Jones and Peter G. Markow, Saint Joseph College

ANAL 728

Identifying an Unknown Aldehyde or Ketone Jan William Simek, California Polytechnic University Derivatives of unknown aldehydes and ketones are prepared. Qualitative tests are performed on the unknown compounds. Results of the qualitative tests, the derivative melting points, and refractive indices are used to identify the unknown compounds from a list of aldehydes and ketones. (2.5 hrs.)

Alcohol content of beer or wine samples is determined using acid dichromate reaction and visible spectroscopy. A standard curve is generated for analysis. Procedure uses milliliter volumes of reagents. (2.5–3 hrs.)

KINETICS

KINE 733

ANAL 729

The Kinetics of Solvolysis of 2-Chloro-2Methylpropane

Identifying an Unknown Alcohol

William H. Brown, Beloit College

Jan William Simek, California Polytechnic University

The rate of reaction of 2-chloro-2-methylpropane with aqueous 2-propanol is measured by determining the amount of hydrochloric acid produced. The rate data are evaluated graphically to demonstrate the dependency of reaction rate on 2chloro-2-methylpropane concentration. (2 hrs.)

Derivatives of unknown alcohols are prepared. Qualitative tests are performed on the unknown compounds. Results of the qualitative tests, the derivative melting points, refractive indices, and boiling points are used to identify the unknown compounds from a list of alcohols. (2–2.5 hrs.)

NEW! KINE 755 ANAL 735

Catalytic Hydrogenation of Unknowns

Synthesis and Kinetics of the Lophine Radical (Semi-Microscale)

Karen C. Weaver, University of Central Arkansas

Carl T. Wigal, Lebanon Valley College

Unknown compounds are reacted with hydrogen gas using a palladium-carbon catalyst. The hydrogenation data and molecular formulas are used to determine the number of pi bonds and rings in the compounds. (2 hrs.)

Lophine is synthesized from benzil and benzaldehyde. The lophine dimer is generated by reaction with N-iodosuccinimide. Lophine radicals are produced by treatment of the dimer with light, and the kinetics of dimer reformation are studied using visible spectroscopy. (3 hrs.)



General Chemistry

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ORGANIC CHEMISTRY L ABS

Technology

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MISCELLANEOUS

Nitrating Acetanilide or Methyl Benzoate: Electrophilic Aromatic Substitution

MISC 744

Carl T. Wigal, Lebanon Valley College


Naming Organic Compounds Joe Jeffers, Ouachita Baptist University Patterns and rules for common and systematic nomenclature are given for common organic compounds. Numerous exercises are included.

Either acetanilide or methyl benzoate is nitrated with HNO3/H2SO4, using a procedure adaptable to either semimicroscale or microscale techniques. Melting point data are used to determine which regioisomer is formed. (3 hrs.)

REAC 734

REACTIONS

Molecular Rearrangement Reactions: Azobenzene and Benzilic Acid

REAC 712

Jerry Manion, University of Central Arkansas

Dehydrating Cyclohexanol

trans-Azobenzene is isomerized to cis-azobenzene using sunlight. The reaction is monitored using TLC. Benzilic acid is produced by reacting benzil with aqueous potassium hydroxide. Benzilic acid is characterized by melting point and IR spectroscopy. Procedure is microscale. (3 hrs.)

Carl T. Wigal, Lebanon Valley College Cyclohexanol is dehydrated with H3PO4/H2SO4 to form cyclohexene. Procedures are given for semi-microscale and microscale techniques. Characterization is done by performing qualitative tests for alcohols and alkenes, by measuring the refractive index of the product, and/or by generating IR spectra for both cyclohexanol and cyclohexene. (2.5 hrs.)

REAC 736

The Pinacol Rearrangement Jerry Manion, University of Central Arkansas

REAC 714

Studying SN1 and SN2 Reactions: Nucleophilic Substitution at a Saturated Carbon Jerry Manion, University of Central Arkansas 1-Butanol is converted to 1-bromobutane with HBr/H2SO4. Procedures are given for microscale and macroscale techniques. Boiling point, density, refractive index, and/or infrared spectroscopy can characterize the product. The effect of three factors on the rate of SN1 reactions are investigated: identity of the leaving group, structure of the alkyl group, and the polarity of the solvent. (2.5–3 hrs.)

REAC 715

Pinacol is rearranged to pinacolone using sulfuric acid. Procedures are given using microscale and semi-microscale techniques. The reactant and product are characterized by qualitative tests. Product is characterized by derivative melting point, IR, or NMR spectroscopy. (3 hrs.)

REAC 741

Free Radical Chlorination Jerry Manion, University of Central Arkansas 1-Chlorobutane is reacted with sulfuryl chloride to produce four dichlorobutane products. Procedure is microscale. Relative reactivities of each hydrogen type are determined from gas chromatographic analysis of the products. (2 hrs.)

Reducing Benzil Using Sodium Borohydride Joseph W. LeFevre, SUNY, Oswego

REAC 742

Benzil is reduced using sodium borohydride. Procedures are given for using microscale and semi-microscale techniques. The product can be identified using melting point, mixture melting point, TLC , and/or IR spectroscopy. (2.5–3 hrs.)

Acid-Catalyzed Hydration of 1-Hexene to Make 2-Hexanol Louis J. Liotta, Stonehill College 1-Hexene is reacted with aqueous sulfuric acid to produce 2hexanol, confirming Markovnikov orientation of addition. Procedures are given using microscale and semi-microscale


70

REAC 716


General Chemistry

Organic Chemistry

Technology



SYNTHESIS

REAC 747

SYNT 713

Hydroboration and Oxidation of 1-Hexene to Make 1-Hexanol

Preparing Isopentyl Acetate by the Fischer Esterification

Louis J.Liotta , Stonehill College

Ronald J. Wikholm, University of Connecticut

The anti-Markovnikov alcohol, 1-hexanol, is prepared by hydroboration of 1-hexene with borane in tetrahydrofuran, followed by oxidation with hydrogen peroxide and sodium hydroxide. Procedures are given using microscale and semi-microscale techniques. Anhydrous techniques are employed. Ratios of Markovnikov to anti-Markovnikov products are determined using GC. Products are characterized by IR and/or NMR spectroscopy. An excellent companion to REAC 742. (4–6 hrs.)

Isopentyl acetate is prepared by reacting acetic acid with isopentyl alcohol, using either H2SO4 or Dowex® 50 as the catalyst. Procedures are given for semi-microscale and microscale techniques. GC, IR, and/or NMR spectroscopy can characterize the product. (2–3 hrs.)

SYNT 717

The Diels–Alder Reaction of Anthracene with Maleic Anhydride

REAC 749

L. G. Wade, Jr., Whitman College

Nucleophilic Aromatic Substitution: The Reaction of 3,4-Dichloronitrobenzene with Sodium Methoxide Jerry Manion, University of Central Arkansas 3,4-Dichloronitrobenzene is reacted with sodium methoxide to produce one of three possible products. Product identity is determined by melting point and mixture melting point. Procedures are given using microscale and semi-microscale techniques. (3 hrs.)

Maleic anhydride and anthracene are reacted in xylene to form 9,10-dihydroanthracene–9,10-α,β-succinic anhydride. Procedures are given for using semi-microscale and microscale techniques. The product is characterized by melting point and IR spectroscopy. (2.5–3 hrs.)

SYNT 718

Nucleophilic Addition to Carbonyl: Grignard Reaction with an Aldehyde Jan William Simek, California Polytechnic State University

REAC 750

Cannizzaro Reaction: The Conversion of p-Nitrobenzaldehyde into p-Nitrobenzoic Acid and p-Nitrobenzyl Alcohol A. T. Rowland, Gettysburg College p-Nitrobenzaldehyde is reacted with 30% potassium hydroxide to produce p-nitrobenzoic acid and p-nitrobenzyl alcohol via a simultaneous oxidization and reduction. Procedure is at the border between microscale and semi-microscale. Products are characterized by melting point and TLC. (3 hrs.)

The Grignard reagent isopropylmagnesium bromide is prepared from 2-bromopropane and reacted with 4-methoxybenzaldehyde to form 1-(4-methoxyphenyl)-2-methylpropan-1-ol. The procedure is given for using semi-microscale techniques. The product is characterized by using TLC, IR, and/or NMR spectroscopy. (3–4 hrs.)

SYNT 719

Brominating Alkenes Carl T. Wigal, Lebanon Valley College Cinnamic acid, cis-stilbene, and trans-stilbene are brominated with pyridinium tribromide to form the corresponding vicinal dihalides. Procedures are given for using semi-microscale and microscale techniques. Melting points and/or silver nitrate tests characterize the products. (1.5–4.5 hrs.)



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techniques. The products are analyzed by GC and by IR or NMR spectroscopy. (3–4 hrs.)

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SYNT 720

SYNT 725

The Aldol Condensation: Synthesis of Dibenzalacetone

Oxidizing Methoxybenzyl Alcohol to Methoxybenzaldehyde Using Phase-Transfer Catalysis


L. G. Wade, Jr., Whitman College Acetone is added to benzaldehyde to form dibenzalacetone. Procedures are given for semi-microscale and microscale techniques. The product is characterized by melting point. (2–2.5 hrs.)

Methoxybenzaldehyde is prepared by oxidizing methoxybenzyl alcohol with sodium hypochlorite using a phase transfer agent. Procedures are given using microscale and semi-microscale techniques. The reaction is monitored by TLC. The product is characterized by infrared spectroscopy. (2.5–3 hrs.)

SYNT 721

Synthesis of trans-9-(2-Phenylethenyl) Anthracene: A Wittig Reaction William M. Loffredo, East Stroudsburg University The alkene trans-9-(2-phenylethenyl)anthracene is synthesized from 9-anthraldehyde and the ylide derived from triphenylbenzylphosphonium chloride. Procedures are given for semimicroscale and microscale techniques. Melting point, TLC, IR, and/or NMR spectroscopy characterize the product. (3 hrs.)

SYNT 726

Two Methods for the Synthesis of Phenacetin Jerry Manion, University of Central Arkansas Phenacetin is prepared using the Williamson ether synthesis and using amide synthesis. Procedures are given using microscale and semi-microscale techniques. Products are characterized by mixture melting point, IR or NMR spectroscopy. (2.5–3 hrs.)

SYNT 723

SYNT 730

Friedel–Crafts Acylation: Synthesis of 4Methoxyacetophenone

Dyes and Dyeing

Jerry Manion, University of Central Arkansas

Orange II is prepared by diazotizing sulfanilic acid and coupling it with 2-naphthol. Orange II, Malachite Green, and Congo Red are used in direct dyeing cloth strips. The strips are bleached with oxidizing and reducing agents. Cloth strips are dyed with reduced indigo and observed during air oxidation. Procedure is semi-microscale. (3 hrs.)

4-Methoxyacetophenone is synthesized by the Friedel–Crafts acylation of anisole with acetic anhydride. The procedure is given for semi-microscale techniques. Melting point, IR, and/or NMR spectroscopy characterize the product. (4 hrs.)

SYNT 724

L.G. Wade, Jr., Whitman College

SYNT 731

Friedel–Crafts Alkylation: Kinetic Versus Thermodynamic Control Jerry Manion, University of Central Arkansas The Friedel–Crafts alkylation of m-xylene with 2-bromopropane is carried out under conditions favoring kinetic control and under conditions favoring thermodynamic control. The procedure is adaptable to either semi-microscale or microscale techniques. The product mixture is anaylzed by GC and IR spectroscopy. (4 hrs.)

Luminol Synthesis and Chemiluminescence Carl T. Wigal, Lebanon Valley College Luminol is prepared from 3-nitrophthalic acid. Its chemiluminescence properties are examined in the presence and absence of quenchers. Procedure is semi-microscale. (3 hrs.)

SYNT 732

Isolating Caffeine from Tea Robert Silberman, SUNY, Cortland, and William M. Loffredo, East Stroudsburg University Caffeine is extracted from tea using dichloromethane. Caffeine is purified by either recrystallization or sublimation. Mass percent of caffeine in tea is calculated. (2.5–3 hrs.)


72

Joseph W. LeFevre, SUNY Oswego


General Chemistry

Organic Chemistry

Technology



Thiamine-Catalyzed Benzoin Condensation Carl T. Wigal, Lebanon Valley College Benzoin is prepared from benzaldehyde by the benzoin condensation. Procedures are given using microscale and semimicroscale techniques. Product is characterized by melting point and IR spectroscopy. (2–3 hrs.)

SYNT 738

Copper-Catalyzed Oxidation of Benzoin to Benzil Carl T. Wigal, Lebanon Valley College Benzil is prepared from benzoin by copper-catalyzed oxidation. Procedures are given using microscale and semi-microscale techniques. Reaction is monitored by TLC. Product is characterized by melting point and IR spectroscopy. (3 hrs.)

SYNT 745

Synthesizing Aspirin: The Acetylation of Salicylic Acid Joe Jeffers, Ouachita Baptist University Acetylsalicylic acid is prepared by reacting salicylic acid with acetic anhydride. Procedures are given using microscale and semi-microscale techniques. The product is characterized by melting point and by reaction with iron(III) chloride. Commercial aspirin is also characterized by reaction with iron(III) chloride. (2 hrs.)

SYNT 746

Acetaminophen: The Acetylation of p-Aminophenol Joe Jeffers, Ouachita Baptist University

SYNT 739

The Synthesis of a Superabsorbent Polymer Charles M. Garner, Baylor University Polyacrylic acid is prepared by the free-radical polymerization of acrylic acid with methylenebisacrylamide crosslinking. The polymer is characterized by its ability to absorb distilled water and 0.2% NaCl. It is further characterized by its reaction with 1M HCl. (2.5–3 hrs.)

Acetaminophen is prepared by reacting p-aminophenol with acetic anhydride. Procedures are given using microscale and semi-microscale techniques. Extent of reaction is monitored by TLC. The product is characterized by melting point and by IR spectroscopy. (2–2.5 hrs.)

SYNT 748

Formation of Benzyne and Its Diels-Alder Reaction: A Multistep Reaction Sequence

SYNT 740

L. G. Wade, Jr., Whitman College

Preparing Ethanol by Fermentation

Benzil and 1,3-diphenyl acetone are reacted in a base-catalyzed aldol condensation to produce a diene. Anthranilic acid is diazotized to produce an unstable diazonium salt that gives rise to benzyne. Benzyne and the diene undergo a Diels-Alder reaction to trap the benzyne adduct as 1,2,3,4-tetraphenylnaphthalene. Procedures are given using microscale and semi-microscale techniques. Not all steps are highly prescribed. Students are expected to make solutions based on yields obtained. Product is characterized by melting point, IR, and/or NMR spectroscopy. (5–8 hrs.)

Joe Jeffers, Ouachita Baptist University Ethanol is prepared from sucrose by yeast fermentation. Procedures are given using microscale, semi-microscale, and macroscale techniques. Fermentation requires a week. Product yield is determined from density measurement. (3 hrs.)

SYNT 743

Converting Benzaldehyde to Benzilic Acid: A Multistep Synthesis Carl T. Wigal, Lebanon Valley College, and Jerry Manion, University of Central Arkansas Benzilic acid is prepared from benzaldehyde in three synthesis steps. First, benzaldehyde is used to make benzoin by a thiamine-catalyzed benzoin condensation. Second, benzoin is converted to benzil by a copper-catalyzed oxidation. Third, benzil is rearranged to benzilic acid by reaction with aqueous NaOH. Procedures are given using microscale and semi-microscale



NEW! SYNT 754

A Multi-Step Synthesis Sequence: An Aldol Condensation, A Michael Addition, and Ethylene Ketal Formation (Microscale and Semi-Microscale)


techniques. Products are characterized by melting point and IR spectroscopy. (9 hrs.)

SYNT 737

A. T. Rowland, Gettysburg College In the first synthesis, P-anisaldehyde and acetone are reacted in an aldol condensation to form dianisalacetone. In the second

General Chemistry

Organic Chemistry


Technology

73



synthesis, dianisalacetone undergoes a Michael addition with dimethylmalonate under catalysis by methoxide ion. In the third synthesis, the Michael product is reacted with ethylene glycol and an acid catalyst to prepare an ethylene ketal product. Products are characterized by melting point and NMR. (8–9 hrs.)

TECHNIQUES

TECH 700

Purifying Acetanilide by Recrystallization Carl Wigal, Lebanon Valley College An appropriate recrystallizing solvent is selected from a group of solvents and used to separate and purify acetanilide from a mixture. The melting points of impure and recrystallized acetanilide are measured and compared. (2–2.5 hrs.)

TECH 704

Practicing Safety in the Organic Chemistry Laboratory Michael W. Rapp, University of Central Arkansas The basic rules of laboratory safety are reviewed. Common hazards in the organic laboratory are identified and proper responses to incidents that may occur in the laboratory are presented. Information is given about the National Fire Protection Association’s diamond and Material Safety Data Sheets. A safety contract and a safety quiz are included.

Separating Cyclohexane and Toluene by Distillation Jerry Manion, University of Central Arkansas Two miscible liquids are separated, either by macroscale or microscale process, using simple and fractional distillation. The efficiencies of simple and fractional distillation are compared. (2–3 hrs.)

TECH 705

Separating Acids and Neutral Compounds by Solvent Extraction

TECH 701

Measuring the Melting Points of Compounds and Mixtures Joseph W. LeFevre, SUNY, Oswego The melting points of pure benzoic acid and pure mandelic acid are measured. The eutectic composition and the eutectic temperature of benzoic acid–mandelic acid mixtures are determined. An unknown compound is identified using mixture melting points. (2.5–3 hrs.)

Jerry Manion, University of Central Arkansas Solvent extraction techniques are used to separate a mixture consisting of a carboxylic acid, a phenol, and a neutral compound. Both microscale and macroscale processes are presented. (3 hrs.)

TECH 706

Separating Camphor from Beta-Carotene by Sublimation

TECH 702

Joseph W. LeFevre, SUNY, Oswego

Using Microscale Techniques

Camphor is separated from beta-carotene by sublimation. The melting points of the purified camphor and beta-carotene are measured and compared to the literature values. An optional part of the experiment is to obtain the UV–visible spectrum of the separated beta-carotene and compare it to a standard beta-carotene spectrum. (2–3 hrs.)

Joe Jeffers, Ouachita Baptist University Glassware commonly found in microscale procedures is used. Small amounts of materials are weighed and transferred. Air or nitrogen is used to speed evaporation of volatile solvents. The percent recovery of benzoic acid dissolved in acetone is calculated. A micropipet is calibrated. The density of cyclohexane is calculated. The refractive index and boiling point of cyclohexane is measured. An unknown is identified using physical properties. (3 hrs.)

TECH 707

Separating a Mixture of Biphenyl, Benzhydrol, and Benzophenone by Thin-Layer Chromatography Ronald J. Wikholm, University of Connecticut A solvent is selected from a group of solvents to separate a mixture of biphenyl, benzhydrol, and benzophenone by TLC. The mixture compounds are identified by comparing Rf values with


74

TECH 703


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Organic Chemistry

Technology



TECH 722

Isolating Clove Oil from Cloves Using Steam Distillation Joseph W. LeFevre, SUNY, Oswego

TECH 708

Separating Ferrocene and Acetylferrocene by Adsorption Column Chromatography Joe Jeffers, Ouachita Baptist University An adsorption chromatography column is prepared either using the dry pack method or the slurry pack method. A two-compound mixture is separated using column chromatography. The percent recovery for each compound is calculated. (2.5–3 hrs.)

Clove oil is isolated from cloves by steam distillation and extraction. Procedures are given for semi-microscale and microscale techniques. The product is characterized by bromine, potassium permanganate, and iron(III) chloride tests. The purity of the product is found from TLC. (3–4 hrs.)

NEW! TECH 752

Resolving a Racemic Mixture: Using (-)-Proline to Separate (+)-Phenylsuccinic Acid (Semi-Microscale) Joe Jeffers, Ouachita Baptist University

TECH 709

Separating and Identifying Mixtures by Gas Chromatography L. G. Wade, Jr., Whitman College

Racemic phenylsuccinic acid is resolved by reaction with (-)-proline to generate the (+)-isomer and, optionally, the (-)-isomer. Product is characterized by melting point and optical rotation. (3 hrs.)

Volatile compounds of mixtures are separated, detected, and identified by gas chromatography. The response ratios of separated compounds are calculated. An unknown mixture is analyzed, identifying and quantifying its components. (2 hrs.)

TECH 710

Identifying an Unknown Compound by Infrared Spectroscopy Moses Lee, Furman University IR samples of benzoic acid and p-anisaldehyde are prepared and the IR spectra are obtained. A liquid unknown is identified from its IR spectrum. (1 hr.)

TECH 711

Using NMR Spectroscopy to Identify an Unknown Organic Compound Joseph W. LeFevre, SUNY, Oswego An unknown compound is characterized after acquiring a spectrum using either continuous-wave or Fourier-transform 1H NMR spectroscopy. The compound may be further characterized after acquiring 13C and DEPT NMR spectroscopy. 1H, 13C, and DEPT NMR spectra of 4-propoxybenzaldehyde are provided for interpretation. (0.3–2 hrs.)



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Organic Chemistry



reference compounds. The solvent polarity effects on the relative mobilities of these compounds in a mixture is investigated. The specific compounds in a mixture containing any combination of the compounds are identified by TLC. (2–2.5 hrs.)

Technology

75

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