Macroscale And Microscale Organic Experiments / With Cd - 4th edition

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.

1. Introduction
2. Laboratory Safety and Waste Disposal

Techniques

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

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 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