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Other titles in the Brooks/Cole Laboratory Series for Organic Chemistry series:
Introduction to Organic Laboratory Techniques: A Small-Scale Approach
Synopses & Reviews
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 project-based 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.
Book News Annotation:
Featuring 66 experiments, detailing 29 techniques, and including several explicating essays, this lab manual covers basic lab techniques, molecular modeling, properties and reactions of organic compounds, the identification of organic substances, project-based experiments, and each step of the various techniques. The authors teach at Western Washington University and North Seattle Community College.
Annotation ©2004 Book News, Inc., Portland, OR (booknews.com)
Featuring new experiments, a new essay, and new coverage of nanotechnology, this organic chemistry laboratory book offers a comprehensive treatment of laboratory techniques including small-scale and some microscale methods that use standard-scale ("macroscale") glassware and equipment. The book is organized based on essays and topics of current interest and covers a large number of traditional organic reactions and syntheses, as well as experiments with a biological or health science focus. Seven introductory technique-based experiments, thirteen project-based experiments, and sections on green chemistry and biofuels, spark reader interest.
About the Author
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, Fourth Edition (Brooks/Cole), and A SMALL SCALE APPROACH TO ORGANIC LABORATORY TECHNIQUES, Third Edition (Brooks/Cole), as well as MICROSCALE AND MACROSCALE TECHNIQUES IN THE ORGANIC LABORATORY (Brooks/Cole), which highlights techniques to be used with a faculty member's own experiments. He is a co-author, with Gary M. Lampman and George S. Kriz, of an organic spectroscopy book, INTRODUCTION TO SPECTROSCOPY, Fourth Edition (Brooks/Cole). 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.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, Fourth Edition (Brooks/Cole), and A SMALL SCALE ARPPROACH TO ORGANIC LABORATORY TECHNIQUES, Third Edition (Brooks/Cole), as well as MICROSCALE AND MACROSCALE TECHNIQUES IN THE ORGANIC LABORATORY (Brooks/Cole), which highlights techniques to be used with a faculty member's own experiments. He is a co-author, with Donald L. Pavia and George S. Kriz, of an organic spectroscopy book, INTRODUCTION TO SPECTROSCOPY, Fourth Edition (Brooks/Cole). 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), Sigma Xi, and the Washington College Chemistry Teachers Association.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. 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. 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, Fourth Edition (Brooks/Cole), and A SMALL SCALE APPROACH TO ORGANIC LABORATORY TECHNIQUES, Third Edition (Brooks/Cole). Their book, MICROSCALE AND MACROSCALE TECHNIQUES IN THE ORGANIC LABORATORY (Brooks/Cole), includes techniques only, and can be used with a faculty member's own experiments. He is a co-author, with Donald Pavia and Gary Lampman, of an organic spectroscopy book, INTRODUCTION TO SPECTROSCOPY, Fourth Edition (Brooks/Cole). Professors 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.Randall G. Engel has taught chemistry for almost 30 years. He has co-authored with Donald Pavia, Gary Lampman, and George Kriz INTRODUCTION TO ORGANIC LABORATORY TECHNIQUES: A MICROSCALE APPROACH, Fourth Edition (Brooks/Cole), and A SMALL SCALE INTRODUCTION TO ORGANIC LABORATORY TECHNIQUES, Third Edition (Brooks/Cole). Their book, MICROSCALE AND MACROSCALE TECHNIQUES IN THE ORGANIC LABORATORY (Brooks/Cole), 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.
Table of Contents
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 Boiling-Point Determination. Essay: Aspirin. Experiment 7. Acetylsalicylic Acid. Essay: Analgesics. Experiment 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-Diethyl-m-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: PROJECT-BASED EXPERIMENTS. Experiment 56. Preparation of a C-4 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. 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: Procedure for Preparing Derivatives. Appendix 3: Index of Spectra.
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