Higher Education

A Microscale Approach to Organic Laboratory Techniques, 5th Edition

  • Donald L. Pavia Western Washington University
  • George S. Kriz Western Washington University
  • Gary M. Lampman Western Washington University
  • Randall G. Engel North Seattle Community College
  • ISBN-10: 1133106528  |  ISBN-13: 9781133106524
  • 1040 Pages
  • Previous Editions: 2007, 1999, 1995
  • © 2013 | Published
  • College Bookstore Wholesale Price = $291.00
  • Newer Edition Available
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About

Overview

From biofuels, green chemistry, and nanotechnology, this proven laboratory textbook provides the up-to-date coverage students need in their coursework and future careers. The book's experiments, all designed to utilize microscale glassware and equipment, cover traditional organic reactions and syntheses, the isolation of natural products, and molecular modeling and include project-based experiments and experiments that have a biological or health science focus. Updated throughout with new and revised experiments, new and revised essays, and revised and expanded techniques, the Fifth Edition is organized based on essays and topics of current interest.

Features and Benefits

  • 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.

Table of Contents

PART I: INTRODUCTION TO BASIC LABORATORY TECHNIQUES.
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: Simple and Fractional Distillation.
Experiment 8: Infrared Spectroscopy and Boiling Point Determination.
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.
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.
PART II: INTRODUCTION TO MOLECULAR MODELING.
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.
PART III: PROPERTIES AND REACTIONS OF ORGANIC COMPOUNDS.
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: Petroleum and Fossil Fuels.
Experiment 26: Gas Chromatographic Analysis of Gasolines.
ESSAY: Biofuels.
Experiment 27: Biodiesel.
ESSAY: Green Chemistry.
Experiment 28: Chiral Reduction of Ethyl Acetoacetate; Optical Purity Determination Using a Chiral Shift Reagent.
Experiment 29: Nitration of Aromatic Compounds Using a Recyclable Catalyst.
Experiment 30: Resolution of (Phenylethylamine and Determination of Optical Purity.
Experiment 31: An Oxidation-Reduction Scheme: Borneol, Camphor, Isoborneol.
Experiment 32: Multi-Step Reaction Sequences: The Conversion of Benzaldehyde to Benzilic Acid.
Experiment 33: Triphenylmethanol and Benzoic Acid.
Experiment 34: Sonogashira Coupling of Iodosubstituted Aromatic Compounds with Alkynes Using a Palladium Catalyst.
Experiment 35: Grubbs-Catalyzed Metathesis of Eugenol with 1,4-Butanediol to Prepare a Natural Product.
Experiment 36: Aqueous-based Organozinc Reactions.
Experiment 37: The Aldol Condensation Reaction: Preparation of Benzalacetophenones (Chalcones).
Experiment 38: Preparation of an -Unsaturated Ketone via Michael and Aldol Condensation Reactions.
Experiment 39: The Wittig Reaction: Preparation of 1,4-Diphenyl-1,3-butadiene.
Experiment 40: Relative Reactivities of Several Aromatic Compounds.
Experiment 41: Nitration of Methyl Benzoate.
ESSAY: Local Anesthetics.
Experiment 42: Benzocaine.
Experiment 43: Methyl Salicylate (Oil of Wintergreen).
ESSAY: Pheromones: Insect Attractants and Repellents.
Experiment 44: N,N-Diethyl-m-toluamide: The Insect Repellent "OFF."
ESSAY: Sulfa Drugs.
Experiment 45: Sulfa Drugs: Preparation of Sulfanilamide.
Essay: Polymers and Plastics.
Experiment 46: Preparation and Properties of Polymers: Polyester, Nylon, and Polystyrene.
Essay: Diels-Alder Reactions and Insecticides.
Experiment 47: The Diels-Alder Reaction of Cyclopentadiene with Maleic Anhydride.
Experiment 48: Diels-Alder Reaction with Anthracene-9-methanol.
Experiment 49: Photoreduction of Benzophenone and Rearrangement of Benzpinacol to Benzopinacolone.
ESSAY:Fireflies and Photochemistry.
Experiment 50: Luminol.
ESSAY: The Chemistry of Sweeteners.
Experiment 51: Analysis of a Diet Soft Drink by HPLC.
PART IV: IDENTIFICATION OF ORGANIC SUBSTANCES.
Experiment 52: Identification of Unknowns.
PART V: PROJECT-BASED EXPERIMENTS.
Experiment 53: Preparation of a C-4 or C-5 Acetate Ester.
Experiment 54: Isolation of Essential Oils from Allspice, Cloves, Cumin, Caraway, Cinnamon, Fennel, or Star Anise.
Experiment 55: Competing Nucleophiles in SN1 and SN2 Reactions: Investigations using 2-Pentanol and 3-Pentanol.
Experiment 56: Friedel-Crafts Acylation.
Experiment 57: The Analysis of Antihistamine Drugs by Gas Chromatography-Mass Spectrometry.
Experiment 58: The Use of Organozinc Reagents in Synthesis: An Exercise in Synthesis and Structure Proof by Spectroscopy.
Experiment 59: Synthesis of Naproxen by Palladium Catalysis.
Experiment 60: The Aldehyde Enigma.
Experiment 61: Synthesis of Substituted Chalcones: A Guided-Inquiry Experience.
Experiment 62: Green Epoxidation of Chalcones.
Experiment 63: Cyclopropanation of Chalcones.
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.
Technique 27: Carbon-13 Nuclear Magnetic Resonance Spectroscopy
Technique 28: Mass Spectrometry.
Technique 29: Guide to the Chemical Literature.
APPENDICES:
Appendix 1: Tables of Unknowns and Derivatives.
Appendix 2: Procedures for Preparing Derivatives.
Appendix 3: Index of Spectra.

What's New

  • A new essay on Biofuels enhances this edition's "in the news" topics.
  • Two new Green Chemistry experiments involve techniques such as solid phase extraction and the use of a microwave reaction system.
  • In two experiments, chiral gas chromatography is now included in the analysis of the products obtained.
  • Eight new experiments have been added: Experiment 2, Solubility; Experiment 27, Biodiesel; Experiment 34, Sonogashira Coupling of Iodosubstituted Aromatic Compounds with Alkynes Using a Palladium Catalyst; Experiment 35, Grubbs-Catalyzed Metathesis of Eugenol with 1,4-Butanediol to Prepare a Natural Product; Experiment 48: Diels-Alder Reaction with Anthracene-9-methanol; Experiment 59, Synthesis of Naproxen (Aleve®) by Palladium Catalysis; Experiment 62, Green Epoxidation of Chalcones; and Experiment 63, Cyclopropanation of Chalcones.
  • Four experiments have been revised: Experiment 31, An Oxidation-Reduction Scheme: Borneol, Camphor, Isoborneol; Experiment 44, N,N-Diethyl-m-toluamide: The Insect Repellant "OFF"; Experiment 52, Identification of Unknowns; and Experiment 56, Friedel-Crafts Acylation.
  • Essays on Petroleum and Fossil Fuels and The Chemistry of Sweeteners have been revised.
  • Four Techniques have been revised and expanded: Technique 7, Reaction Methods, has been extensively revised to include information on working under an inert atmosphere; Technique 12, Extractions, Separations, and Drying Agents, now includes new material on instructions on drawing separation schemes; Technique 25, Infrared Spectroscopy, now includes the use of ATR for infrared analysis of solids; and Technique 26, Nuclear Magnetic Resonance Spectroscopy, includes new material on analysis of diastereotopic protons.
  • A new method of obtaining boiling points and monitoring distillations using a temperature probe with one of the Vernier devices or a digital thermometer has been introduced.

Learning Resource Bundles

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Bundle: A Microscale Approach to Organic Laboratory Techniques, 5th + Pushing Electrons, 4th + Organic Chemistry, 7th + Chemical Principles for Organic Chemistry + OWLv2 with Student Solutions Manual 24-Months Printed Access Card

ISBN-10: 1305521625 | ISBN-13: 9781305521629

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Supplements

All supplements have been updated in coordination with the main title. Select the main title's "About" tab, then select "What's New" for updates specific to title's edition.

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Instructor Supplements

Online Instructor's Manual  (ISBN-10: 1133177018 | ISBN-13: 9781133177012)

Available for download as a PDF file to qualified instructors, this manual contains complete instructions for the preparation of reagents and equipment for each experiment, the estimated time to complete each experiment, answers to the questions, notes for special equipment or reagent handling, and suggested waste disposal guidelines. In some cases, additional optional experiments are included.

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Meet the Author

Author Bio

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.