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Organic Experiments

Organic Experiments - 8th edition

Organic Experiments - 8th edition

ISBN13: 9780395865194

ISBN10: 0395865190

Organic Experiments by Louis E. Fieser and Kenneth L. Williamson - ISBN 9780395865194
Edition: 8TH 98
Copyright: 1998
Publisher: Houghton Mifflin Harcourt
International: No
Organic Experiments by Louis E. Fieser and Kenneth L. Williamson - ISBN 9780395865194

ISBN13: 9780395865194

ISBN10: 0395865190

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For the introductory organic lab course, this manual offers a series of clear and concise experiments that encourage accurate observation and the development of deductive reasoning. The author places strong emphasis on safety and responsible disposal of hazardous waste.

  • Extensive references to relevant Web sites are included at the end of most chapters.
  • The order of the chapters has been changed to follow that of most organic textbooks. Similar types of experiments are now grouped together.
  • Experiments make use of less expensive, safer solvents.
  • The chapters on Molecular Mechanics and NMR Spectroscopy have been rewritten and exercises have been added. Exercises in computational chemistry are integrated throughout the manual.
  • In the Instructor's Guide, each experiment now includes information on the time needed to carry out the experiment and the degree of difficulty of the experiment.
  • Pedagogical features include prelab exercises, marginal notes, clear line drawings, and questions for the student to answer. Answers to the questions are provided in the Instructor's Guide.
  • At the end of every experiment, a Cleaning Up section instructs the students on how to dispose of all by-products used in the experiment.

Table of Contents

Table of Contents

1. Introduction
2. Laboratory Safety and Waste Disposal


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: 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
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 Reactions

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 Reaction

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 x-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 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