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Organic Experiments

Organic Experiments - 9th edition

ISBN13: 978-0618308422

Cover of Organic Experiments 9TH 04 (ISBN 978-0618308422)
ISBN13: 978-0618308422
ISBN10: 0618308423
Cover type: Hardback
Edition/Copyright: 9TH 04
Publisher: Houghton Mifflin Harcourt
Published: 2004
International: No
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Organic Experiments - 9TH 04 edition

ISBN13: 978-0618308422

Kenneth Williamson and Louis Fieser

ISBN13: 978-0618308422
ISBN10: 0618308423
Cover type: Hardback
Edition/Copyright: 9TH 04
Publisher: Houghton Mifflin Harcourt

Published: 2004
International: No
Summary

This text for the 2-semester introductory organic chemistry lab offers a series of clear and concise experiments that encourage accurate observation and deductive reasoning. An engaging prose and a focus on biochemical and biomedical applications render the narrative ideally suited for the mainstream organic chemistry laboratory. Emphasis is placed on safety and the disposal of hazardous waste.

Pre-lab exercises, marginal notes, clear line drawings, and questions help retain student interest and comprehension from lesson to lesson. This new edition includes "In this experiment" objectives that clarify the goals of procedures. Optional, additional "For Further Investigation" features offer an in-depth exploration of the chemical principles presented. Students may also determine the precise structure of molecules using the "Computational Chemistry" computer-based calculations.

  • New! This edition includes material on mass spectroscopy in Chapter 14.
  • The experiments presented make use of less costly and safe solvents.
  • Extensive references to relevant Websites allow students to further explore chemical concepts.
  • A supplementary Instructor's Guide contains assessments of the relative difficulty of--and time needed for--each experiment, as well as trouble-shooting tips, answers to end-of-chapter questions, a list of chemicals and apparatus required for each experiment per student and per 24-hour student laboratory, sources of supply for unusual items, and a guide for the hardware and software needed for running computational chemistry and molecular mechanics experiments.

Table of Contents

1. Introduction
2. Laboratory Safety and Waste Disposal

Techniques

3. Crystallization
4. Melting Points and Boiling Points
5. Distillation
6. Steam Distillation
7. Vacuum Distillation and Sublimation
8. Extraction: Isolation of Caffeine from Tea and Cola Syrup
9. Thin-Layer Chromatography: Analysis of Analgesics and Isolation of Lycopene from Tomato Paste
10. Column Chromatography: Acetyl Ferrocene, 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 and Mass Spectroscopy **note change in chapter title to reflect inclusion of new material
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
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
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 Synthesis: Synthesis of a Barbiturate
43. Amines
44. Separation and Purification of the Components of an Analgesic Tablet: Aspirin, Caffeine, and Acetaminophen
45. The Sandmeyer Reaction: 4-Chlorotoluene and 2-Iodobenzoic Acid
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 Phenylcinnamic Acid
61. Decarboxylation: Synthesis of cis-Stilbene Photochemistry
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 B-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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