Macroscale and Microscale Organic Experiments

by Williamson, Kenneth L.; Masters, Katherine M.

• ISBN13: 9780538733335
• ISBN10: 0538733330
• Edition: 6th
• Format: Hardcover
• Copyright: 2010-05-03
• Publisher: Cengage Learning

Summary

The market leader for the full-year organic laboratory, 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 new 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.

Table of Contents

Introduction

Laboratory Safety, Courtesy, and Waste Disposal Techniques

Melting Points and Boiling Points

Recrystallization

Distillation

Steam Distillation, Vacuum Distillation, and Sublimation

Extraction

Thin-Layer Chromatography: Analysis of Analgesics and Isolating Lycopene from Tomato Paste

Column Chromatography: Fluorenone, Cholesteryl Acetate, Acetylferrocene, and Plant Pigments

Gas Chromatography: Analysis of Alkene Isomers

Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Mass Spectroscopy

Ultraviolet Spectroscopy, Refractive Indices, and Qualitative Instrumental Organic Analysis

Computational Chemistry Elimination, Substitution, and Addition

The SN2 Reaction: 1-Bromobutane

Nucleophilic Substitution Reactions of Alkyl Halides

Radical Initiated Chlorination of 1-Chlorobutane

Alkenes from Alcohols: Cyclohexene from Cyclohexanol

Bromination and Debromination: Purification of Cholesterol

Dichlorocarbene Oxidation and Reduction

Oxidation: Cyclohexanol to Cyclohexanone

Cyclohexanone to Adipic Acid

The Cannizzaro Reaction: Simultaneous Synthesis of an Alcohol and an Acid in the Absence of Solvent

Oxidative Coupling of Alkynes: 2,7-Dimethyl-3,5-octadiyn-2,7-diol

Catalytic Hydrogenation

Sodium Borohydride Reduction of 2-Methylcyclohexanone: a Problem in Conformational Analysis

Epoxidation of Cholesterol

Aromatic Substitution and Elimination

Nitration of Methyl Benzoate

Friedel-Crafts Alkylation of Benzene and Dimethoxybenzene; Host-Guest Chemistry

Alkylation of Mesitylene

The Friedel-Crafts Reaction: Anthraquinone and Anthracene

Friedel-Crafts Acylation of Ferrocene: Acetylferrocene

Reactions of Triphenylmethyl Carbocation, Carbanion, and Radical

1,2,3,4-Tetraphenylnaphthalene via Benzyne

Triptycene via Benzyne Reactions of Aldehydes and Ketones

Aldehydes and Ketones

Dibenzalacetone by the Aldol Condensation

Grignard Synthesis of Triphenylmethanol and Benzoic Acid

The Wittig and Wittig-Horner Reactions Reactions of Carboxylic Acids, Esters, and Amines

Esterification and Hydrolysis

Acetylsalicylic Acid (Aspirin)

Malonic Ester of a Barbiturate

Amines

The Sandmeyer Reaction: 1-Bromo-4-chlorobenzene, 2-Iodobenzoic Acid, and 4-Chlorotoluene

Synthesis and Bioessay of Sulfanilamide and Derivatives

Dyes and Dyeing

Martius Yellow

Diels-Alder Reaction

Ferrocene [Bis(cyclopentadienyl)iron]

A Diels-Alder Reaction Puzzle: the Reaction of 2,4-Hexadien-1-ol with Maleic Anhydride

Tetraphenylcyclopentadienone

Hexaphenylbenzene and Dimethyl Tetraphenylphthalate

Derivatives of 1,2-Diphenylethane: a Multistep Synthesis

The Benzoin Condensation: Catalysis by the Cyanide Ion and Thiamine

Nitric Acid Oxidation

Preparation of Benzil from Benzoin; and Synthesis of a Heterocycle: Diphenylquinoxaline

Borohydride Reduction of a Ketone: Hydrobenzoin from Benzil

The Synthesis of 2,2-Dimethyl-1,5-dioxolane

The Acetonide Derivative of a Vicinal Diol

The 1,4-Addition: Reductive Acetylation of Benzil

Synthesis of an Alkyne from an Alkene

Bromination and Dehydrobromination: Stilbene and Diphenylacetylene

The Perkin Reaction: Synthesis of a-Phenylcinnamic Acid

Multicomponent Reactions: the Aqueous Passerini Reaction

Chemiluminescence: Syntheses of Cyalume and Luminol

Photochemistry: the Synthesis of Benzopinacol Natural Product Chemistry and Biochemistry

Carbohydrates and Sweeteners

Virstatin, a Possible Treatment for Cholera

Biosynthesis of Ethanol and Enzymatic Reactions

The Synthesis of Natural Products: Pseudopellitierene and Camphor

Polymers: Synthesis and Recycling

Searching the Chemical Literature

Table of Contents provided by Publisher. All Rights Reserved.