"Macroscale and Microscale Organic Experiments" by Kenneth L. Williamson, Katherine M. Masters

This manual derives many experiments and procedures from the classic Feiser lab text, giving it an unsurpassed reputation for solid, authoritative content. The book includes experiments that stress greener chemistry, updated NMR spectra, and a Premium Website that includes glassware-specific videos with pre-lab exercises.

Offering a flexible mix of macroscale and microscale options for most experiments, this proven manual allows users to save on the purchase and disposal of expensive, sometimes hazardous organic chemicals. Macroscale versions can be used for less costly experiments, giving readers experience working with conventionally sized glassware.

Contents
Preface
Organic Experiments and Waste Disposal
1: Introduction
2: Laboratory Safety, Courtesy, and Waste Disposal
Techniques
3: Melting Points and Boiling Points
4: Recrystallization
5: Distillation
6: Steam Distillation, Vacuum Distillation, and Sublimation
7: Extraction
8: Thin-Layer Chromatography: Analyzing Analgesics and Isolating Lycopene from Tomato Paste
9: Column Chromatography: Fluorenone, Cholesteryl Acetate, Acetylferrocene, and Plant Pigments
10: Gas Chromatography: Analyzing Alkene Isomers
11: Infrared Spectroscopy
12: Nuclear Magnetic Resonance Spectroscopy
13: Mass Spectrometry
14: Ultraviolet Spectroscopy, Refractive Indices, and Qualitatibe Instrumental Organic Analysis
15: Computational Chemistry
The Synthetic Experiments
16: The SN2 Reaction: 1-Bromobutane
17: Nucleophilic Substitution Reactions of Alkyl Halides
18: Radical Initiated Chlorination of 1-Chlorobutane
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: The Cannizzaro Reaction: Simultaneous Synthesis of an Alcohol and an Acid in the Absence of Solvent
24: Oxidative Coupling of Alkynes: 2,7-DimethyI-3,5-octadiyn- 2,7-diol
25: Catalytic Hydrogenation
26: Sodium Borohydride Reduction of2-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: The Friedel—Crafts Reaction: Anthraquinone and Anthracene
32: Friedel—Crafts Acylation of Ferrocene: Acetylferrocene
33: Reactions of Triphenylmethyl Carbocation, Carbanion, and Radical
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: The Wittig and Wittig-Horner Reactions
Reactions of Carboxylic Acids, Esters, and Amines
40: Esterification and Hydrolysis
41: Acetylsalicylic Acid(Aspirin)
42: Malomc Ester of a Barbiturate
43: Amines
44: The Sandmeyer Reaction: 1-Bromo-4-chlorobenzene, 2-lodobenzoic Acid, and 4-Chlorotoluene
45: Synthesis and Bioassay of Sulfanilamide and Derivatives
46: Dyes and Dyeingl
47: Martius Yellow
The Diels—Alder and Related Reactions
48: Diels—Alder Reaction
49: Ferrocene [Bis(cyclopentadienyl)iron]
50: A Diels—Alder ReactionPuzzle: The Reaction of 2,4-Hexadien-1-ol with Maleic Anhydride
51: Tetraphenylcyclopentadienone
52: Hexaphenylbenzene and Dimethyl TetraphenyIphthalate
Derivatives of 1,2-Diphenylethane: A Multistep Synthesis
53: The Benzoin Condensation: Catalysis by the Cyanide Ion and Thiamine
54: Nitric Acid Oxidation; Preparation of Benzil from Benzoin, and Synthesis of a Heterocycle: Diphenylquinoxaline
55: The Borohydride Reductionof a Ketone: Hydrobenzoinfrom Benzil
65: Biosynthesis of Ethanol and Enzymatic Reactions
56: The Synthesis of 2,2-Dimethy 1-1,5-Dioxolane, The Acetonide Derivative of a Vicinal Diol
57: 1,4-Addition: Reductive Acetylation of Benzil
58: The Synthesis of an Alkyne from an Alkene, Bromination and Dehydrobromination: Stilbene and Diphenylacetylene
59: The Perkin Reaction: Synthesis of D-Phenylcinnamic Acid and Its Decarboxylation to cis-Stilbene
60: Multicomponent Reactions: The Aqueous Passerini Reaction
Photochemistry
61: Chemiluminescence: Syntheses of Cyalume and Luminol
62: Photochemistry: The Synthesis of Benzopinacol
Natural Product Chemistry and Biochemistry
63: Carbohydrates and Sweeteners
64: Virstatin, a Possible Treatment for Cholera
65: Biosynthesis of Ethanol and Enzymatic Reactions
66: The Synthesis of Natural Products: The Sex Attractan tof the Cockroach and Camphor
67: Polymers: Synthesis and Recycling
68: Searching the Chemical Literature
Index