Organic Chemistry

[Pages:368]Organic Chemistry

Second Edition

The INSTANT NOTES series

Series Editor: B.D. Hames School of Biochemistry and Molecular Biology, University of Leeds, Leeds, UK

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Organic Chemistry

Second Edition

G. L. Patrick

Department of Chemistry and Chemical Engineering, Paisley University, Paisley, Scotland

This edition published in the Taylor & Francis e-Library, 2005.

"To purchase your own copy of this or any of Taylor & Francis or Routledge's collection of thousands of eBooks please go to eBookstore. tandf.co.uk."

? Garland Science/BIOS Scientific Publishers, 2004

First published 2000 Second edition published 2004

All rights reserved. No part of this book may be reproduced or transmitted, in any form or by any means, without permission.

A CIP catalogue record for this book is available from the British Library.

ISBN 0-203-42761-0 Master e-book ISBN

ISBN 0-203-44168-0 (Adobe eReader Format) ISBN 1 85996 264 5 (Print Edition)

Garland Science/BIOS Scientific Publishers 4 Park Square, Milton Park, Abingdon, Oxon OX14 4RN, UK and 29 West 35th Street, New York, NY 10001?2299, USA World Wide Web home page: bios.co.uk Garland Science/BIOS Scientific Publishers is a member of the Taylor & Francis Group

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Library of Congress Cataloging-in-Publication Data Patrick, Graham L.

Organic chemistry / G.L. Patrick.--2nd ed. p. cm. -- (Instant notes series)

Includes bibliographical references and index. ISBN 1-85996-264-5 (alk. paper) 1. Chemistry, Organic--Outlines, syllabi, etc. I. Title: Instant notes organic chemistry. II. Title. III. Series. QD256.5.P37 2003 547--dc22

Production Editor: Andrew Watts

CONTENTS

Preface

ix

Section A ? Structure and bonding

1

A1 Atomic structure of carbon

1

A2 Covalent bonding and hybridization

3

A3 sp3 Hybridization

5

A4 sp2 Hybridization

8

A5 sp Hybridization

14

A6 Bonds and hybridized centers

17

Section B ? Alkanes and cycloalkanes

19

B1 Definition

19

B2 Drawing structures

20

B3 Nomenclature

22

Section C ? Functional groups

27

C1 Recognition of functional groups

27

C2 Aliphatic and aromatic functional groups

29

C3 Intermolecular bonding

30

C4 Properties and reactions

33

C5 Nomenclature of compounds with functional groups

35

C6 Primary, secondary, tertiary and quaternary

nomenclature

43

Section D ? Stereochemistry

45

D1 Constitutional isomers

45

D2 Configurational isomers ? alkenes and cycloalkanes

46

D3 Configurational isomers ? optical isomers

49

D4 Conformational isomers

56

Section E ? Nucleophiles and electrophiles

63

E1 Definition

63

E2 Charged species

64

E3 Neutral inorganic species

66

E4 Organic structures

69

Section F ? Reactions and mechanisms

73

F1 Reactions

73

F2 Mechanisms

75

Section G ? Acid?base reactions

79

G1 Br?nsted?Lowry acids and bases

79

G2 Acid strength

82

G3 Base strength

88

G4 Lewis acids and bases

94

G5 Enolates

95

vi

Section H ? Alkenes and alkynes

99

H1 Preparation of alkenes and alkynes

99

H2 Properties of alkenes and alkynes

101

H3 Electrophilic addition to symmetrical alkenes

105

H4 Electrophilic addition to unsymmetrical alkenes

112

H5 Carbocation stabilization

115

H6 Reduction and oxidation of alkenes

117

H7 Hydroboration of alkenes

121

H8 Electrophilic additions to alkynes

124

H9 Reduction of alkynes

127

H10 Alkylation of terminal alkynes

129

H11 Conjugated dienes

131

Section I ? Aromatic chemistry

135

I1 Aromaticity

135

I2 Preparation and properties

137

I3 Electrophilic substitutions of benzene

139

I4 Synthesis of mono-substituted benzenes

147

I5 Electrophilic substitutions of mono-substituted

aromatic rings

150

I6 Synthesis of di- and tri-substituted benzenes

160

I7 Oxidation and reduction

164

Section J ? Aldehydes and ketones

167

J1 Preparation

167

J2 Properties

169

J3 Nucleophilic addition

173

J4 Nucleophilic addition ? charged nucleophiles

175

J5 Electronic and steric effects

181

J6 Nucleophilic addition ? nitrogen nucleophiles

184

J7 Nucleophilic addition ? oxygen and sulfur

nucleophiles

187

J8 Reactions of enolate ions

191

J9 -Halogenation

198

J10 Reduction and oxidation

200

J11 ,-Unsaturated aldehydes and ketones

202

Section K ? Carboxylic acids and carboxylic acid derivatives

205

K1 Structure and properties

205

K2 Nucleophilic substitution

209

K3 Reactivity

213

K4 Preparations of carboxylic acids

217

K5 Preparations of carboxylic acid derivatives

219

K6 Reactions

224

K7 Enolate reactions

234

Section L ? Alkyl halides

239

L1 Preparation and physical properties of alkyl halides

239

L2 Nucleophilic substitution

242

L3 Factors affecting SN2 versus SN1 reactions

247

L4 Elimination

252

L5 Elimination versus substitution

256

L6 Reactions of alkyl halides

258

L7 Organometallic reactions

261

Contents

Contents

vii

Section M ? Alcohols, phenols, and thiols

263

M1 Preparation of alcohols

263

M2 Preparation of phenols

264

M3 Properties of alcohols and phenols

266

M4 Reactions of alcohols

270

M5 Reactions of phenols

277

M6 Chemistry of thiols

281

Section N ? Ethers, epoxides, and thioethers

283

N1 Preparation of ethers, epoxides, and thioethers

283

N2 Properties of ethers, epoxides, and thioethers

286

N3 Reactions of ethers, epoxides, and thioethers

289

Section O ? Amines and nitriles

295

O1 Preparation of amines

295

O2 Properties of amines

299

O3 Reactions of amines

305

O4 Chemistry of nitriles

311

Section P ? Organic spectroscopy and analysis

315

P1 Spectroscopy

315

P2 Visible and ultra violet spectroscopy

317

P3 Infra-red spectroscopy

322

P4 Proton nuclear magnetic resonance spectroscopy

324

P5 13C nuclear magnetic resonance spectroscopy

339

P6 Mass spectroscopy

342

Further reading

347

Index

349

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