Organic Experiments

by Williamson, Kenneth L.

• ISBN13: 9780618308422
• ISBN10: 0618308423
• Edition: 9th
• Format: Hardcover
• Copyright: 2003-07-02
• Publisher: Cengage Learning

Summary

This text for the two-semester introductory organic chemistry lab offers a series of clear and concise experiments that encourage accurate observation and deductive reasoning. A focus on biochemical and biomedical applications renders the narrative ideal for the mainstream organic chemistry laboratory. Emphasis is also 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. The Ninth 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.

Table of Contents

Preface	ix
1 Introduction	1	(18)
2 Laboratory Safety and Waste Disposal	19	(13)
Techniques
3 Crystallization	32	(18)
4 Melting Points, Boiling Points, and Refractive Indices	50	(15)
5 Distillation	65	(12)
6 Steam Distillation	77	(11)
7 Vacuum Distillation and Sublimation	88	(15)
8 Extraction of Acids and Bases and the Isolation of Caffeine from Coffee, Tea, and Cola Syrup	103	(20)
9 Thin-Layer Chromatography: Analysis of Analgesics and Isolation of Lycopene from Tomato Paste	123	(15)
10 Column Chromatography: Acetylferrocene, Cholesteryl Acetate, and Fluorenone	138	(10)
11 Alkenes from Alcohols: Analysis of a Mixture by Gas Chromatography	148	(7)
12 Infrared Spectroscopy	155	(22)
13 Nuclear Magnetic Resonance Spectroscopy	177	(19)
14 Ultraviolet Spectroscopy and Mass Spectrometry	196	(15)
15 Molecular Mechanics and Computational Chemistry	211	(9)
Elimination, Substitution, and Addition
16 The SN2 Reaction: 1-Bromobutane	220	(6)
17 Nucleophilic Substitution Reactions of Alkyl Halides	226	(7)
18 Alkanes and Alkenes: Radical Initiated Chlorination of 1-Chlorobutane; Reactions of Alkanes and Alkenes	233	(12)
19 Alkenes from Alcohols: Cyclohexene from Cyclohexanol	245	(6)
20 Bromination and Debromination: Purification of Cholesterol	251	(5)
21 Dichlorocarbene	256	(8)
Oxidation and Reduction
22 Oxidation: Cyclohexanol to Cyclohexanone; Cyclohexanone to Adipic Acid	264	(11)
23 Pulegone from Citronellol: Oxidation with Pyridinium á Chlorochromate	275	(8)
24 Oxidative Coupling of Alkynes: 2,7-Dimethyl-3,5-octadiyn-2,7-diol	283	(4)
25 Catalytic Hydrogenation	287	(10)
26 Sodium Borohydride Reduction of 2-Methylcyclohexanone: A Problem in Conformational Analysis	297	(6)
27 Epoxidation of Cholesterol	303	(6)
Aromatic Substitution and Elimination
28 Nitration of Methyl Benzoate	309	(5)
29 Friedel-Crafts Alkylation of Benzene and Dimethoxybenzene; Host-Guest Chemistry	314	(11)
30 Alkylation of Mesitylene	325	(7)
31 Reactions of Triphenylmethyl Carbocation, Carbanion, and Radical	332	(12)
32 The Friedel-Crafts Reaction: Anthraquinone and Anthracene	344	(8)
33 Friedel-Crafts Acylation of Ferrocene: Acetylferrocene	352	(3)
34 1,2,3,4-Tetraphenylnaphthalene via Benzyne	355	(4)
35 Triptycene via Benzyne	359	(5)
Reactions of Aldehydes and Ketones
36 Aldehydes and Ketones	364	(19)
37 Dibenzalacetone by the Aldol Condensation	383	(5)
38 Grignard Synthesis of Triphenylmethanol and Benzoic Acid	388	(13)
39 The Wittig and Wittig-Horner Reactions	401	(6)
Reactions of Carboxylic Acids, Esters, and Amines
40 Esterification and Hydrolysis	407	(9)
41 Acetylsalicylic Acid (Aspirin)	416	(6)
42 Malonic Ester Synthesis of a Barbiturate	422	(7)
43 Amines	429	(10)
44 Separation and Purification of the Components of an Analgesic Tablet: Aspirin Caffeine, and Acetaminophen	439	(5)
45 The Sandmeyer Reaction: 1-Bromo-4-chlorobenzene, 2-lodobenzoic Acid, and 4-Chlorotoluene	444	(7)
46 Sulfanilamide from Nitrobenzene	451	(13)
47 Dyes and Dyeing	464	(17)
48 Martius Yellow	481	(8)
The Diels-Alder and Related Reactions
49 Diels-Alder Reaction	489	(13)
50 Ferrocene [Bis(cyclopentadienyl)iron]	502	(6)
51 p-Terphenyl by the Diels-Alder Reaction	508	(3)
52 Tetraphenylcyclopentadienone	511	(3)
53 Hexaphenylbenzene and Dimethyl Tetraphenylphthalate	514	(5)
Derivatives of 1,2-Diphenylethane: A Multistep Synthesis	519	(39)
54 The Benzoin Condensation: Cyanide Ion and Thiamine Catalyzed	521	(5)
55 Nitric Acid Oxidation. Preparation of Benzil from Benzoin. Synthesis of a Heterocycle: Diphenylquinoxaline	526	(6)
56 Borohydride Reduction of a Ketone: Hydrobenzoen from Benzil	532	(3)
57 Synthesis of 2,2-Dimethyl- 1,5-dioxolane. The Acetonide Derivative of a Vicinal Diol	535	(3)
58 1,4-Addition: Reductive Acetylation of Benzil	538	(4)
59 Synthesis of an Alkyne from an Alkene. Bromination and Dehydrobromination: Stilbene and Diphenylacetylene	542	(7)
60 The Perkin Reaction: Synthesis of a-Phenylcinnamic Acid	549	(5)
61 Decarboxylation: Synthesis of cis-Stilbene	554	(4)
Photochemistry
62 Chemiluminescence: Syntheses of Cyalume and Luminol	558	(8)
63 Photochemistry: The Synthesis of Benzopinacol	566	(7)
Natural Product Chemistry and Biochemistry
64 Carbohydrates and Sweeteners	573	(7)
65 Biosynthesis of Ethanol	580	(8)
66 Enzymatic Reactions: A Chiral Alcohol from a Ketone and Enzymatic Resolution of DL-Alanine	588	(12)
67 Isolation of Lycopene and ß-Carotene	600	(4)
68 The Synthesis of Natural Products: Pseudopellitierene and Camphor	604	(10)
69 Polymers: Synthesis and Recycling	614	(20)
70 Qualitative Organic Analysis	634	(37)
71 Searching the Chemical Literature	671
Index