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Organic Experiments,9780618308422
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Organic Experiments

by
Edition:
9th
ISBN13:

9780618308422

ISBN10:
0618308423
Format:
Hardcover
Pub. Date:
7/2/2003
Publisher(s):
Cengage Learning
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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 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 -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


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