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THE VOCABULARY AND CONCEPTS
OF ORGANIC CHEMISTRY
THE VOCABULARY AND
CONCEPTS OF ORGANIC
CHEMISTRY
SECOND EDITION
Milton Orchin
Roger S. Macomber
Allan R. Pinhas
R. Marshall Wilson
A John Wiley & Sons, Inc., Publication
Copyright © 2005 by John Wiley & Sons, Inc. All rights reserved.
Published by John Wiley & Sons, Inc., Hoboken, New Jersey.
Published simultaneously in Canada.
No part of this publication may be reproduced, stored in a retrieval system, or transmitted in any form
or by any means, electronic, mechanical, photocopying, recording, scanning, or otherwise, except as
permitted under Section 107 or 108 of the 1976 United States Copyright Act, without either the prior
written permission of the Publisher, or authorization through payment of the appropriate per-copy fee to
the Copyright Clearance Center, Inc., 222 Rosewood Drive, Danvers, MA 01923, 978-750-8400, fax
978-646-8600, or on the web at www.copyright.com. Requests to the Publisher for permission should
be addressed to the Permissions Department, John Wiley & Sons, Inc., 111 River Street, Hoboken, NJ
07030, (201) 748-6011, fax (201) 748-6008.
Limit of Liability/ Disclaimer of Warranty: While the publisher and author have used their best efforts
in preparing this book, they make no representations or warranties with respect to the accuracy or
completeness of the contents of this book and specifically disclaim any implied warranties of
merchantability or fitness for a particular purpose. No warranty may be created or extended by sales
representatives or written sales materials. The advice and strategies contained herein may not be
suitable for your situation. You should consult with a professional where appropriate. Neither the
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but not limited to special, incidental, consequential, or other damages.
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however, may not be available in electronic format.
Library of Congress Cataloging-in-Publication Data is available.
ISBN 0-471-68028-1
Printed in the United States of America
10987654321
CONTENTS
1 Atomic Orbital Theory
1
2 Bonds Between Adjacent Atoms: Localized Bonding,
Molecular Orbital Theory
25
3 Delocalized (Multicenter) Bonding
54
4 Symmetry Operations, Symmetry Elements, and
Applications
83
5 Classes of Hydrocarbons
110
6 Functional Groups: Classes of Organic Compounds
139
7 Molecular Structure Isomers, Stereochemistry, and
Conformational Analysis
221
8 Synthetic Polymers
291
9 Organometallic Chemistry
343
10 Separation Techniques and Physical Properties
387
11 Fossil Fuels and Their Chemical Utilization
419
12 Thermodynamics, Acids and Bases, and Kinetics
450
13 Reactive Intermediates (Ions, Radicals, Radical Ions,
Electron-Deficient Species, Arynes)
505
14 Types of Organic Reaction Mechanisms
535
15 Nuclear Magnetic Resonance Spectroscopy
591
v
vi
CONTENTS
16 Vibrational and Rotational Spectroscopy: Infrared, Microwave,
and Raman Spectra
657
17 Mass Spectrometry
703
18 Electronic Spectroscopy and Photochemistry
725
Name Index
833
Compound Index
837
General Index
849
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