Macroscale and Microscale Organic Experiments

by Williamson, Kenneth L; Minard, Robert D; Masters, Katherine M

• ISBN13: 9780618590674
• ISBN10: 0618590676
• Edition: 5th
• Format: Hardcover
• Copyright: 2006-03-02
• Publisher: Brooks Cole

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 Williamson/Minard/Masters manual's flexible mix of macroscale and microscale options for most experiments allows instructors to save on the purchase and disposal of expensive, sometimes hazardous organic chemicals. Macroscale versions can be used for less costly experiments, giving students experience working with conventionally sized glassware. The Fifth Edition of the manual includes new experiments that stress greener chemistry, revised content in computational chemistry, and more information on laboratory safety procedures. New! Experiments that stress greener chemistry appear throughout the manual and are identified with a green chemistry icon. For example, the use of household bleach is explored as an alternative to the toxic chromium ion as an oxidizing agent for cyclohexanol. New! The laboratory safety chapter now includes material on working with closed systems and laboratory courtesy. New! The chapter on mass spectrometry describes time-of-flight and mass quadrupole analyzers, and includes sections on GC-MS and computer-aided spectral identification as well as ESI and MALDI ionization. New! Bioassay experiments include a bioassay of eugenol isolated from cloves. New! Material is now offered on diffuse reflectance IR analysis, capillary GC, and temperature programming. Revised! The place of organic chemistry labwork has been put in a broader context via reorganization of and revisions to the first fifteen chapters dealing with basic lab methods, computational chemistry, and instrumental methods. Revised! Computational chemistry, which allows students to determine the precise structure of molecules, has been extensively revised to provide extended coverage of ab initio and semi-empirical models and calculations. Revised! The discussions of NMR theory and the interpretation of 1HNMR spectra have been updated. The In this experiment... section appears before selected microscale experiments and presents the overarching objective of the experiment, keeping students from getting bogged down in the details of experimental procedures. For Further Investigation procedures appear in selected experiments. These are optional, additional procedures that can be assigned to further explore the chemical principle being presented. A Cleaning Up section appears at the end of every experiment and instructs students on how to dispose of all the by-products used in the experiment. Other pedagogical features include pre-lab exercises, marginal notes, clear line drawings, and end-of-chapter questions.

Table of Contents

Introduction

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

Pulegone from Citronellol: Oxidation with Pyridinium Chlorochromate

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 The Diels-Alder and Related Reactions

Diels-Alder Reaction

Ferrocene [Bis(cyclopentadienyl)iron]

p-Terphenyl by the Diels-Alder Reaction

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 ofa-Phenylcinnamic Acid

Decarboxylation: Synthesis ofcis-Stilbene Photochemistry

Chemiluminescence: Syntheses of Cyalume and Luminol

Photochemistry: The Synthesis of Benzopinacol Natural Product Chemistry and Biochemistry

Carbohydrates and Sweeteners

Biosynthesis of Ethanol

Enzymatic Reactions: A Chiral Alcohol from a Ketone and Enzymatic Resolution of DL-A

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