Macroscale and Microscale Organic Experiments

by WILLIAMSON

• ISBN13: 9780669243468
• ISBN10: 0669243469
• Edition: 2nd
• Format: Paperback
• Copyright: 1993-12-30
• Publisher: Brooks Cole

Summary

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.

Table of Contents

1 Introduction	1	(25)
2 Laboratory Safety and Waste Disposal	26	(13)
3 Crystallization	39	(25)
4 Melting Points, Boiling Points, and Refractive Indices	64	(17)
5 Distillation	81	(11)
6 Steam Distillation	92	(18)
7 Vacuum Distillation and Sublimation	110	(16)
8 Extraction of Acids and Bases and the Isolation of Caffeine from Instant Coffee, Tea, and Cola Syrup	126	(27)
9 Cholesterol from Human Gallstones	153	(4)
10 Thin-Layer Chromatography: Analysis of Analgesics and Isolation of Lycopene from Tomato Paste	157	(13)
11 Column Chromatography: Acetylferrocene, Cholesteryl Acetate, Fluorenone, Lycopene, and Carotene	170	(13)
12 Liquid Chromatography	183	(5)
13 Infrared Spectroscopy	188	(18)
14 Nuclear Magnetic Resonance Spectroscopy	206	(19)
15 Ultraviolet Spectroscopy	225	(7)
16 Molecular Mechanics	232	(8)
17 Nucleophilic Substitution Reactions of Alkyl Halides	240	(7)
18 The S(N)2 Reaction: 1-Bromobutane	247	(8)
19 Alkanes and Alkenes: Chlorination of 1-Chlorobutane; Tests for Alkanes and Alkenes	255	(13)
20 Alkenes from Alcohols: Analysis of a Mixture by Gas Chromatography	268	(10)
21 Synthesis and Reactions of Alkenes: Cyclohexene from Cyclohexanol	278	(6)
22 Catalytic Hydrogenation	284	(10)
23 Bromination and Debromination: Purification of Cholesterol	294	(6)
24 Epoxidation of Cholesterol	300	(4)
25 Diels-Alder Reaction	304	(15)
26 p-Terphenyl by the Diels-Alder Reaction	319	(4)
27 Ferrocene Bis(cyclopentadienyl)iron	323	(7)
28 Reactions of Triphenylmethyl Carbocation, Carbanion, and Radical	330	(11)
29 Oxidation: Cyclohexanol to Cyclohexanone; Cyclohexanone to Adipic Acid	341	(14)
30 Pulegone from Citronellol: Oxidation with Pyridinium Chlorochromate	355	(9)
31 Grignard Synthesis of Triphenylmethanol and Benzoic Acid	364	(15)
32 Acetylsalicyclic Acid (Aspirin)	379	(6)
33 Esterification and Hydrolysis	385	(15)
34 Aldehydes and Ketones	400	(17)
35 Dibenzalacetone by Aldol Condensation	417	(6)
36 Nitration of Methyl Benzoate	423	(5)
37 Alkylation of Mesitylene	428	(7)
38 Friedel-Crafts Alkylation of Benzene and Dimethoxybenzene; Host--Guest Chemistry	435	(14)
39 The Friedel-Crafts Reaction: Anthraquinone and Anthracene	449	(12)
40 Tetraphenylcyclopentadienone	461	(3)
41 Triptycene via Benzyne	464	(5)
42 Hexaphenylbenzene and Dimethyl Tetraphenylphthalate	469	(5)
43 The Wittig and Wittig-Horner Reactions	474	(7)
44 Friedel-Crafts Acylation of Ferrocene: Acetylferrocene	481	(4)
Derivatives of 1,2-Diphenylethane: A Multistep Synthesis	485	(266)
45 The Benzoin Condensation: Cyanide Ion and Thiamine Catalyzed	487	(7)
46 Nitric Acid Oxiation; Preparation of Benzil from Benzoin; Synthesis of a Heterocycle: Diphenylquinoxaline	494	(6)
47 Borohydride Reduction of a Ketone: Hydrobenzoin from Benzil	500	(3)
48 1,4-Addition: Reductive Acetylation of Benzil	503	(5)
49 Synthesis of an Alkyne from an Alkene; Bromination and Dehydrobromination: Stilbene and Diphenylacetylene	508	(8)
50 The Perkin Reaction: Synthesis of Beta-Phenylcinnamic Acid	516	(5)
51 Decarboxylation: Synthesis of cis-Stilbene	521	(5)
52 Amines	526	(10)
53 Separation and Purification of the Components of an Analgesic Tablet: Aspirin, Caffeine, and Acetaminophen	536	(5)
54 Sulfanilamide from Nitrobenzene	541	(17)
55 The Sandmeyer Reaction: 1-Bromo-4-chlorobenzene, 2-lodobenzoic Acid, and 4-Chlorotoluene	558	(10)
56 Malonic Ester Synthesis: Synthesis of a Barbiturate	568	(9)
57 Dichlorocarbene	577	(9)
58 Photochemistry: The Synthesis of Benzopinacol	586	(8)
59 Biosynthesis of Ethanol	594	(11)
60 Oxidative Coupling of Alkynes: 2, 7-Dimethyl-3, 5-octadiyn-2, 7-diol	605	(4)
61 Carbohydrates and Sweeteners	609	(7)
62 Martius Yellow	616	(8)
63 Enzymatic Reactions: A Chiral Alcohol from a Ketone and Enzymatic Resolution of DL-Alanine	624	(13)
64 The Synthesis of Natural Products: Pseudopellitierene and Camphor	637	(10)
65 Luminol and Cyalume: Syntheses of Chemiluminescent Substances	647	(8)
66 Dyes and Dyeing	655	(20)
67 Polymers: Synthesis and Recycling	675	(21)
68 Glass Blowing	696	(7)
69 Qualitative Organic Analysis	703	(37)
70 Sodium Borohydride Reduction of 2-Methylcyclohexanone: A Problem in Conformational Analysis	740	(5)
71 Searching the Chemical Literature	745	(6)
Index	751