Macroscale and Microscale Organic Experiments

by WILLIAMSON

• ISBN13: 9780395902202
• ISBN10: 0395902207
• Edition: 3rd
• Format: Paperback
• Copyright: 1998-11-03
• 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

Preface	xi
Introduction	1	(24)
Laboratory Safety and Waste Disposal	25	(14)
Techniques
Crystallization	39	(27)
Melting Points, Boiling Points, and Refractive Indices	66	(16)
Distillation	82	(17)
Steam Distillation	99	(12)
Vacuum Distillation and Sublimation	111	(16)
Extraction of Acids and Bases and the Isolation of Caffeine from Coffee, Tea, and Cola Syrup	127	(29)
Thin-Layer Chromatography: Analysis of Analgesics and Isolation of Lycopene from Tomato Paste	156	(15)
Column Chromatography: Acetylferrocene, Cholesteryl Acetate, and Fluorenone	171	(12)
Alkenes from Alcohols: Analysis of a Mixture by Gas Chromatography	183	(10)
Infrared Spectroscopy	193	(22)
Nuclear Magnetic Resonance Spectroscopy	215	(19)
Ultraviolet Spectroscopy	234	(7)
Molecular Mechanics and Computational Chemistry Elimination, Substitution, and Addition	241	(9)
Elimination, Substitution, and Addition
The S N 2 Reaction: 1-Bromobutane	250	(8)
Nucleophilic Substitution Reactions of Alkyl Halides	258	(7)
Alkanes and Alkenes: Radical Initiated Chlorination of 1-Chlorobutane; Reactions of Alkanes and Alkenes	265	(13)
Alkenes from Alcohols: Cyclohexene from Cyclohexaol	278	(7)
Bromination and Debromination: Purification of Cholesterol	285	(7)
Dichlorocarbene	292	(9)
Oxidation and Reduction
Oxidation: Cyclohexanol to Cyclohexanone; Cyclohexanone to Adipic Acid	301	(14)
Pulegone from Citronellol: Oxidation with Pyridinium Chlorochromate	315	(10)
Oxidative Coupling of Alkynes: 2,7-Dimethyl-3,5-octadiyn-2,7-diol	325	(5)
Catalytic Hydrogenation	330	(13)
Sodium Borohydride Reduction of 2-Methylcyclohexanone: A Problem in Conformational Analysis	343	(6)
Epoxidation of Cholesterol	349	(6)
Aromatic Substitution and Elimination
Nitration of Methyl Benzoate	355	(5)
Friedel-Crafts Alkylation of Benzene and Dimethoxybenzene; Host-Guest Chemistry	360	(14)
Alkylation of Mesitylene	374	(8)
Reactions of Triphenylmethyl Carbocation, Carbanion, and Radical	382	(13)
The Friedel-Crafts Reaction: Anthraquinone and Anthracene	395	(12)
Friedel-Crafts Acylation of Ferrocene: Acetylferrocene	407	(4)
1,2,3,4-Tetraphenylnaphthalene via Benzyne	411	(6)
Triptycene via Benzyne	417	(5)
Reactions of Aldehydes and Ketons
Aldehydes and Ketones	422	(19)
Dibenzalacetone by the Aldol Condensation	441	(6)
Grignard Synthesis of Triphenylmethanol and Benzoic Acid	447	(17)
The Wittig and Wittig-Horner Reactions	464	(7)
Reactions of Carboxylic Acids, Esters, and Amines
Esterification and Hydrolysis	471	(15)
Acetylsalicylic Acid (Aspirin)	486	(6)
Malonic Ester Synthesis: Synthesis of a Barbiturate	492	(9)
Amines	501	(10)
Separation and Purification of the Components of an Analgesic Tablet: Aspirin, Caffeine, and Acetaminophen	511	(7)
The Sandmeyer Reaction: 1-Bromo-4-chlorobenzene, 2-lodobenzoic Acid, and 4-Chlorotoluene	518	(10)
Sulfanilamide from Nitrobenzene	528	(16)
Dyes and Dyeing	544	(20)
Martius Yellow	564	(8)
The Diets-Alder and Related Reactions
Diels-Alder Reaction	572	(17)
Ferrocene [Bis(cyclopentadienyl)iron]	589	(7)
p-Terphenyl by the Diels-Alder Reaction	596	(4)
Tetraphenylcyclopentadienone	600	(4)
Hexaphenylbenzene and Dimethyl Tetraphenylphthalate	604	(6)
Derivatives of 1,2-Diphenylethane: A Multistep Synthesis	610	(175)
The Benzoin Condensation: Cyanide Ion and Thiamine Catalyzed	612	(6)
Nitric Acid Oxidation. Preparation of Benzil from Benzoin. Synthesis of a Heterocycle: Diphenylquinoxaline	618	(6)
Borohydride Reduction of a Ketone: Hydrobenzoin from Benzil	624	(3)
Synthesis of 2,2-Dimethyl-1,5-dioxolane. The Acetonide Derivative of a Vicinal Diol	627	(3)
1,4-Addition: Reductive Acetylation of Benzil	630	(5)
Synthesis of an Alkyne from an Alkene. Bromination and Dehydrobromination: Stilbene and Diphenylacetylene	635	(10)
The Perkin Reaction: Synthesis of α-Phenylcinnamic Acid	645	(6)
Decarboxylation: Synthesis of cis-Stilbene	651	(5)
Photochemistry
Chemiluminescence: Syntheses of Cyalume and Luminol	656	(8)
Photochemistry: The Synthesis of Benzopinacol	664	(8)
Natural Product Chemistry and Biochemistry
Carbohydrates and Sweeteners	672	(7)
Biosynthesis of Ethanol	679	(10)
Enzymatic Reactions: A Chiral Alcohol from a Ketone and Enzymatic Resolution of DL-Alanine	689	(15)
Isolation of Lycopene and β-Carotene	704	(4)
The Synthesis of Natural Products: Pseudopellitierene and Camphor	708	(11)
Polymers: Synthesis and Recycling	719	(23)
Qualitative Organic Analysis	742	(37)
Searching the Chemical Literature	779	(6)
Index	785