A Microscale Approach to Organic Laboratory Techniques, 6th Edition

Donald L. Pavia, George S. Kriz, Gary M. Lampman, Randall G. Engel

Copyright 2018
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A Microscale Approach to Organic Laboratory Techniques 6th Edition by Donald L. Pavia/George S. Kriz/Gary M. Lampman/Randall G. Engel

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Overview
Meet the Authors
What's New
Features
Table of Contents
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Overview

Featuring new experiments unique to this lab textbook, as well as new and revised essays and updated techniques, this Sixth Edition provides the up-to-date coverage students need to succeed in their coursework and future careers. From biofuels, green chemistry, and nanotechnology, the book’s experiments, designed to utilize microscale glassware and equipment, demonstrate the relationship between organic chemistry and everyday life, with project-and biological or health science focused experiments. As they move through the book, students will experience traditional organic reactions and syntheses, the isolation of natural products, and molecular modeling.

Meet the Authors

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Donald L. Pavia

Donald L. Pavia earned his BS degree in chemistry from Reed College and his PhD in organic chemistry from Yale University. In 1970, he joined the faculty at Western Washington University as Assistant Professor and now holds the rank of Professor Emeritus. He is the coauthor of two organic laboratory books that include techniques and experiments: INTRODUCTION TO ORGANIC LABORATORY TECHNIQUES: A MICROSCALE APPROACH (Cengage Learning), and A SMALL SCALE APPROACH TO ORGANIC LABORATORY TECHNIQUES (Cengage Learning), as well as MICROSCALE AND MACROSCALE TECHNIQUES IN THE ORGANIC LABORATORY (Cengage Learning), which highlights techniques to be used with a faculty member's own experiments. He is a co-author, with Gary M. Lampman, George S. Kriz and James R. Vyvyan of an organic spectroscopy book, INTRODUCTION TO SPECTROSCOPY (Cengage Learning). Professor Pavia's research interests center on the synthesis and reactions of valence tautomeric and photochromic compounds, especially pyrylium-3-oxide tautomers. Autoxidations are a special interest. His other interests include the use of computers in teaching organic chemistry, both for lecture presentation and for the simulation of laboratories. He is the author of several computer programs. One such program is SQUALOR (Simulated Qualitative Organic Analysis) for which he won the 1986 EDUCOM/NCRIPTAL award. The program is designed for teaching the methods for solving organic unknowns.

George S. Kriz

George S. Kriz is Professor of Chemistry at Western Washington University. He earned his B.S. degree in chemistry from the University of California, and his Ph.D. from Indiana University, Bloomington, IN. In 1967 he joined the faculty at Western Washington University and recently served as department chair. He served as the General Chair of the 17th Biennial Conference on Chemical Education for 2001-2002. Professor Kriz was honored with the Peter J. Elich Excellence in Teaching Award (College of Arts and Sciences), Western Washington University, in 2000 and the Distinguised Service Award from the Division of Chemical Education, American Chemical Society (2010). He is the co-author with Donald Pavia, Gary Lampman, and Randall Engel of two organic laboratory books that include both techniques and experiments: INTRODUCTION TO ORGANIC LABORATORY TECHNIQUES: A MICROSCALE APPROACH (Cengage Learning), and A SMALL SCALE APPROACH TO ORGANIC LABORATORY TECHNIQUES (Cengage Learning). Their book, MICROSCALE AND MACROSCALE TECHNIQUES IN THE ORGANIC LABORATORY (Cengage Learning), includes techniques only, and can be used with a faculty member's own experiments. He is a co-author, with Donald Pavia, Gary Lampman, and James Vyvyan, of an organic spectroscopy book, INTRODUCTION TO SPECTROSCOPY (Cengage Learning). Professor Kriz's research interests include: developing new experiments for the organic chemistry laboratory; chemical education and the teaching of chemistry courses for general-understanding audiences; and determination of the structures of natural products using spectroscopic methods.

Gary M. Lampman

Gary M. Lampman earned his BS degree in chemistry from the University of California, Los Angeles, and his PhD in organic chemistry from the University of Washington. In 1964, he joined the faculty at Western Washington University as Assistant Professor, rising to Professor in 1973. He received the Outstanding Teaching Award for the College of Arts and Sciences in 1976. He now holds the title of Professor Emeritus. Teaching has always been an important part of his life. Contact with students invigorates him. He is the coauthor of two organic laboratory books that include techniques and experiments: INTRODUCTION TO ORGANIC LABORATORY TECHNIQUES: A MICROSCALE APPROACH (Cengage Learning), and A SMALL SCALE ARPPROACH TO ORGANIC LABORATORY TECHNIQUES (Cengage Learning), as well as MICROSCALE AND MACROSCALE TECHNIQUES IN THE ORGANIC LABORATORY (Cengage Learning), which highlights techniques to be used with a faculty member's own experiments. He is a co-author, with Donald L. Pavia, George S. Kriz, and James R. Vyvyan of an organic spectroscopy book, INTRODUCTION TO SPECTROSCOPY, Fourth Edition (Cengage Learning). Professor Lampman also is the author of the computer program for teaching organic nomenclature: ORGANIC NOMENCLATURE: AN INTRODUCTION TO THE IUPAC SYSTEM. His research interests center on synthetic methods involving the reaction of free radicals on unsaturated cobaloximes (vitamin B12 model compounds), synthesis of strained small ring compounds, and chemical education. He is the author of 18 papers in these areas. He is a member of the American Chemical Society (Organic and Chemical Education divisions), and the Washington College Chemistry Teachers Association.

Randall G. Engel

Randall G. Engel has taught chemistry for almost 35 years. He has co-authored with Donald Pavia, Gary Lampman, and George Kriz INTRODUCTION TO ORGANIC LABORATORY TECHNIQUES: A MICROSCALE APPROACH (Cengage Learning), and A SMALL SCALE INTRODUCTION TO ORGANIC LABORATORY TECHNIQUES (Cengage Learning). Their book, MICROSCALE AND MACROSCALE TECHNIQUES IN THE ORGANIC LABORATORY (Cengage Learning), includes techniques only, and can be used with a faculty member's own experiments. Engel received his B.A. degree in chemistry from Cornell College and his M.S. degree in chemistry from Western Washington University. He began his teaching career at Wenatchee Valley College in 1975 and continued at Green River Community College and Edmonds Community College. Presently he teaches organic chemistry on a part-time basis at North Seattle Community College.

What's New

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NEW experiments that continue the text's tradition of demonstrating the relationship between organic chemistry and our everyday lives include: A Preparation of Soap, A New Green Oxidation Reaction using Oxone® in an Oxidation-Reduction Scheme, Preparation of Methyl Orange, Preparation of Indigo, and Formulation of a Paint and Art Project.
NEW essays that give further examples of how the text's new experiments are related to our everyday lives, including Soap and Dyes.
A number of experiments are linked together to create multistep syntheses, allowing students to carry out experiments that are different from those of their laboratory peers. For example, when doing a multistep synthesis, some students will carry out the chalcone reaction, others the “green” epoxidation, and still others, cyclopropanation of the resulting chalcones, making the laboratory experience more interesting and rewarding.
Many references in the technique chapters have been updated. New material on diastereotopic protons has been added to Technique 26, Nuclear Magnetic Resonance Spectroscopy, while technique 29, Guide to the Chemical Literature, has been revised.
NEW OWLv2 course with LabSkills PreLab activities that correlate to the topics covered and experiments from the textbook is now available. The course also includes 35 End of Chapter questions on key experiments and a MindTap Reader e-book version of the lab manual.

Features

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A continued emphasis on Green Chemistry decreases the need for hazardous waste disposal, leading to reduced contamination of the environment. Green Chemistry experiments use less toxic reactants and solvents. Almost all experiments have been reduced in scale compared to traditional macroscale experiments.
An alternative way of approaching qualitative analysis that makes extensive use of spectroscopy to solve the structure of organic unknowns. This approach not only shows students how to solve structures in a more modern way, similar to that used in a research laboratory, but also reduces waste considerably.
Open-ended experiments allow students to "write" their own experimental procedures and make their own discoveries.
Infrared, proton NMR, and 13C NMR spectroscopy is incorporated into many experiments. Some experiments also have an option to use gas chromatography-mass spectrometry.
Molecular modeling experiments give students an opportunity to experience the power of molecular modeling software.
Essays and examples on contemporary topics spark student interest and engage them in the learning process.
Experiments are well-written, comprehensive, class-tested, and proven over time.
"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.

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Experiment 1. Introduction to Microscale Laboratory.
Experiment 2. Solubility.
Experiment 3. Crystallization.
Experiment 4. Extraction.
Experiment 5. A Separation and Purification Scheme.
Experiment 6. Chromatography.
Experiment 7. Infrared Spectroscopy and Boiling Point Determination.
Experiment 8. Simple and Fractional Distillation.
Essay: Aspirin.
Experiment 9. Acetylsalicylic Acid.
Essay: Analgesics.
Experiment 10. Isolation of the Active Ingredient in an Analgesic Drug.
Experiment 11, Acetaminophen.
Essay: Identification of Drugs.
Experiment 12. TLC Analysis of Analgesic Drugs.
Essay: Caffeine.
Experiment 13. Isolation of Caffeine from Tea or Coffee.
Essay: Esters -- Flavors and Fragrances.
Experiment 14. Isopentyl Acetate (Banana Oil).
Essay: Terpenes and Phenylpropanoids.
Experiment 15. Essential Oils: Extraction of Oil of Cloves by Steam Distillation.
Essay: Stereochemical Theory of Odor.
Experiment 16. Spearmint and Caraway Oil: (+)- and (-)-Carvones.
Essay: The Chemistry of Vision.
Experiment 17. Isolation of Chlorophyll and Carotenoid Pigments from Spinach.
Essay: Ethanol and Fermentation Chemistry.
Experiment 18. Ethanol from Sucrose.
Essay Molecular Modeling and Molecular Mechanics.
Experiment 19. An Introduction to Molecular Modeling.
Essay: Computational Chemistry -- Ab Initio and Semiempirical Methods.
Experiment 20. Computational Chemistry.
Experiment 21. Reactivities of Some Alkyl Halides.
Experiment 22. Nucleophilic Substitution Reactions: Competing Nucleophiles.
Experiment 23. Synthesis of n-Butyl Bromide and t-Pentyl Chloride.
Experiment 24. 4-Methylcyclohexene.
Essay: Fats and Oils.
Experiment 25. Methyl Stearate from Methyl Oleate.
Essay: Soap.
Experiment 26. Preparation of Soap.
Essay: Petroleum and Fossil Fuels.
Experiment 27. Gas Chromatographic Analysis of Gasolines.
Essay: Biofuels.
Experiment 28. Biodiesel.
Essay: Green Chemistry.
Experiment 29. Chiral Reduction of Ethyl Acetoacetate; Optical Purity Determination.
Experiment 30. Nitration of Aromatic Compounds Using a Recyclable Catalyst.
Experiment 31. Reduction of Ketones Using Carrots as Biological Reducing Agents.
Experiment 32. Resolution of Phenylethylamine and Determination of Optical Purity.
Experiment 33. An Oxidation-Reduction Scheme: Borneol, Camphor, Isoborneol.
Experiment 34. Multi-Step Reaction Sequences: The Conversion of Benzaldehydeto Benzilic Acid.
Experiment 35. Triphenylmethanol and Benzoic Acid.
Experiment 36. Aqueous-based Organozinc Reactions.
Experiment 37. Sonogashira Coupling of Iodosubstituted Aromatic Compounds with Alkynes Using a Palladium Catalyst.
Experiment 38. Grubbs-Catalyzed Metathesis of Eugenol with 1,4-Butanediol to Prepare a Natural Product.
Experiment 39. The Aldol Condensation Reaction: Preparation of Benzalacetophenones (Chalcones).
Experiment 40. A Green Enantioselective Aldol Condensation Reaction.
Experiment 41. Preparation of an Unsaturated Ketone via Michael and Aldol Condensation Reactions.
Experiment 42. Preparation of Triphenylpyridine.
Experiment 43. The Wittig Reaction: Preparation of 1,4-Diphenyl-1,3-Butadiene.
Experiment 44. Relative Reactivities of Several Aromatic Compounds.
Experiment 45. Nitration of Methyl Benzoate.
Essay: Synthetic Dyes.
Experiment 46. Preparation of Methyl Orange.
Experiment 47. Preparation of Indigo.
Experiment 48. Formulation of a Paint and Art Project.
Essay: Local Anesthetics.
Experiment 49. Benzocaine.
Essay: Pheromones: Insect Attractants and Repellents.
Experiment 50. N,N-Diethyl-m-toluamide: The Insect Repellent "OFF".
Essay: Sulfa Drugs.
Experiment 51. Sulfa Drugs: Preparation of Sulfanilamide.
Essay: Polymers and Plastics.
Experiment 52. Preparation and Properties of Polymers: Polyester, Nylon, and Polystyrene.
Essay: Diels-Alder Reactions and Insecticides.
Experiment 53. The Diels-Alder Reaction of Cyclopentadiene with Maleic Anhydride.
Experiment 54. The Diels-Alder Reaction with Anthracene-9-Methanol.
Experiment 55. Photoreduction of Benzophenone and Rearrangement of Benzpinacol to Benzopinacolone.
Essay: Fireflies and Photochemistry.
Experiment 56. Luminol.
Experiment 57. Identification of Unknowns.
Experiment 58. Preparation of a C-4 or C-5 Acetate Ester.
Experiment 59. Competing Nucleophiles in SN1 and SN2 Reactions: Investigations Using 2-Pentanol and 3-Pentanol.
Experiment 60. Friedel-Crafts Acylation.
Experiment 61. The Analysis of Antihistamine Drugs by Gas Chromatography-Mass Spectrometry.
Experiment 62. The Use of Organozinc Reagents in Synthesis: An Exercise in Synthesis and Structure Proof by Spectroscopy.
Experiment 63. Synthesis of Naproxen by Palladium Catalysis.
Experiment 64. The Aldehyde Enigma.
Experiment 65. Synthesis of Substituted Chalcones: A Guided-Inquiry Experience.
Experiment 66. Green Epoxidation of Chalcones.
Experiment 67. Cyclopropanation of Chalcones.
Experiment 68. Michael and Aldol Condensation Reactions.
Experiment 69. Esterification Reactions of Vanillin: The Use of NMR to Solve a Structure Proof Problem.

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 Catalogs.
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.
Technique 27. Carbon-13 Nuclear Magnetic Resonance Spectroscopy.
Technique 28. Mass Spectrometry.
Technique 29. Guide to the Chemical Literature.
Appendix 1: Tables of Unknowns and Derivatives.
Appendix 2: Procedures for Preparing Derivatives.
Appendix 3: Index of Spectra.
Index.