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Macroscale and Microscale Organic Experiments / With CD

Macroscale and Microscale Organic Experiments / With CD - 4th edition

ISBN13: 978-0618333844

Cover of Macroscale and Microscale Organic Experiments / With CD 4TH 03 (ISBN 978-0618333844)
ISBN13: 978-0618333844
ISBN10: 0618333843
Cover type:
Edition/Copyright: 4TH 03
Publisher: Houghton Mifflin Harcourt
Published: 2003
International: No

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Macroscale and Microscale Organic Experiments / With CD - 4TH 03 edition

ISBN13: 978-0618333844

Kenneth L. Williamson

ISBN13: 978-0618333844
ISBN10: 0618333843
Cover type:
Edition/Copyright: 4TH 03
Publisher: Houghton Mifflin Harcourt

Published: 2003
International: No

This flexible, accurate manual includes both macroscale and microscale procedures for each experiment. The level and writing style of the text, which emphasizes biochemical and biomedical applications, make it ideally suited for the mainstream organic chemistry laboratory.

  • A student CD-ROM includes videos and photos related to the material in the text. Videos feature the exact glassware required for each experiment and demonstrate techniques for how to conduct experiments successfully and safely. Photos show lab equipment set-ups.
  • "In this Experiment" is a new feature that appears before every microscale experiment. It presents the objective of the experiment and keeps students from getting bogged down in the minute details of experimental procedures.
  • An instructor web site provides a forum where instructors can communicate directly with the text author about specific experiments and the implementation of microscale techniques. The site also includes PDF files from the Instructor's Resource Manual.

Author Bio

Williamson, Kenneth L. : Mount Holyoke College

Ken Williamson is retired from Mt. Holyoke College where he taught the organic chemistry laboratory course. He is an established authority on microscale techniques who regularly holds workshops and travels to campuses in the U.S., Canada, and Europe to demonstrate the use of microscale.

Table of Contents

1. Introduction
2. Laboratory Safety and Waste Disposal


3. Crystallization
4. Melting Points, Boiling Points, and Refractive Indices
5. Distillation
6. Steam Distillation
7. Vacuum Distillation and Sublimation
8. Extraction of Acids and Bases and the Isolation of Caffeine from Coffee, Tea, and Cola Syrup
9. Thin-Layer Chromatography: Analysis of Analgesics and Isolation of Lycopene from Tomato Paste
10. Column Chromatography: Acetylferrocene, Cholesteryl Acetate, and Fluorenone
11. Alkenes from Alcohols: Analysis of a Mixture by Gas Chromatography
12. Infrared Spectroscopy
13. Nuclear Magnetic Resonance Spectroscopy
14. Ultraviolet Spectroscopy and Mass Spectrometry
15. Molecular Mechanics and Computational Chemistry

Elimination, Substitution, and Addition

16. The SN2 Reaction: 1-Bromobutane
17. Nucleophilic Substitution Reactions of Alkyl Halides
18. Alkanes and Alkenes: Radical Initiated Chlorination of 1-Chlorobutane; Reactions of Alkanes and Alkenes
19. Alkenes from Alcohols: Cyclohexene from Cyclohexanol
20. Bromination and Debromination: Purification of Cholesterol
21. Dichlorocarbene

Oxidation and Reduction

22. Oxidation: Cyclohexanol to Cyclohexanone; Cyclohexanone to Adipic Acid
23. Pulegone from Citronellol: Oxidation with Pyridinium Chlorochromate
24. Oxidative Coupling of Alkynes: 2,7-Dimethyl-3,5-octadiyn-2,7-diol
25. Catalytic Hydrogenation
26. Sodium Borohydride Reduction of 2-Methylcyclohexanone: A Problem in Conformational Analysis
27. Epoxidation of Cholesterol

Aromatic Substitution and Elimination

28. Nitration of Methyl Benzoate
29. Friedel-Crafts Alkylation of Benzene and Dimethoxybenzene; Host-Guest Chemistry
30. Alkylation of Mesitylene
31. Reactions of Triphenylmethyl Carbocation, Carbanion, and Radical
32. The Friedel-Crafts Reaction: Anthraquinone and Anthracene
33. Friedel-Crafts Acylation of Ferrocene: Acetylferrocene
34. 1,2,3,4-Tetraphenylnaphthalene via Benzyne
35. Triptycene via Benzyne

Reactions of Aldehydes and Ketones

36. Aldehydes and Ketones
37. Dibenzalacetone by the Aldol Condensation
38. Grignard Synthesis of Triphenylmethanol and Benzoic Acid
39. Wittig and Wittig-Horner Reaction

Reactions of Carboxylic Acids, Esters and Amines

40. Esterification and Hydrolysis
41. Acetylsalicylic Acid (Aspirin)
42. Malonic Ester of a Barbiturate
43. Amines
44. Separation and Purification of the Components of an Analgesic Tablet: Aspirin, Caffeine, and Acetaminophen

Derivatives of 1,2-Diphenylethane: A Multistep Process

45. The Sandmeyer Reaction: 1-Bromo-4-chlorobenzene-2-Iodobenzoic Acid, and 4-Chlorotoluene
46. Sulfanilamide from Nitrobenzene
47. Dyes and Dyeing
48. Martius Yellow

The Diels-Alder and Related Reactions

49. Diels-Alder Reaction
50. Ferrocene [Bis(cyclopentadienyl)iron]
51. p-Terphenyl by the Diels-Alder Reaction
52. Tetraphenylcyclopentadienone
53. Hexaphenylbenzene and Dimethyl Tetraphenylphthalate

Derivatives of 1,2-Diphenylethane: A Multistep Synthesis

54. The Benzoin Condensation: Cyanide Ion and Thiamine Catalyzed
55. Nitric Acid Oxidation. Preparation of Benzil from Benzoin. Synthesis of a Heterocycle: Diphenylquinoxaline
56. Borohydride Reduction of a Ketone: Hydrobenzoin from Benzil
57. Synthesis of 2,2-Dimethyl-1,5-dioxolane. The Acetonide Derivative of a Vicinal Diol
58. 1,4-Addition: Reductive Acetylation of Benzil
59. Synthesis of an Alkyne from an Alkene. Bromination and Dehydrobromination: Stilbene and Diphenylacetylene
60. The Perkin Reaction: Synthesis of aphha-Phenylcinnamic Acid
61. Decarboxylation: Synthesis of cis-Stilbene


62. Chemiluminescence: Syntheses of Cyalume and Luminol
63. Photochemistry: The Synthesis of Benzopinacol

Natural Product Chemistry and Biochemistry

64. Carbohydrates and Sweeteners
65. Biosynthesis of Ethanol
66. Enzymatic Reactions: A Chiral Alcohol from a Ketone and Enzymatic Resolution of DL-Alanine
67. Isolation of Lycopene and Beta-Carotene
68. The Synthesis of Natural Products: Pseudopellitierene and Camphor
69. Polymers: Synthesis and Recycling
70. Qualitative Organic Analysis
71. Searching the Chemical Literature

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