Quimica organica

Advanced Organic FOURTH Chemistry EDITION
Part A: Structure and Mechanisms

Advanced Organic Chemistry
PART A: Structure and Mechanisms PART B: Reactions and Synthesis

Advanced Organic FOURTH Chemistry EDITION
Part A: Structure and Mechanisms
FRANCIS A. CAREY and RICHARD J. SUNDBERG
University of Virginia Charlottesville, Virginia

Kluwer Academic Publishers
New York, Boston,Dordrecht, London, Moscow

eBook ISBN: Print ISBN:

0-306-46856-5 0-306-46242-7

©2002 Kluwer Academic Publishers New York, Boston, Dordrecht, London, Moscow Print ©2000 Kluwer Academic Publishers New York All rights reserved No part of this eBook may be reproduced or transmitted in any form or by any means, electronic, mechanical, recording, or otherwise, without written consent from thePublisher Created in the United States of America Visit Kluwer Online at: and Kluwer's eBookstore at: http://kluweronline.com http://ebooks.kluweronline.com

Preface to the Fourth Edition
The goal of this text is to build on the foundation of introductory organic chemistry to provide students and other readers a deeper understanding of structure and mechanism and the relationships between them. Wehave provided speci®c data and examples with which to illustrate the general principles that are discussed. Our purpose is to solidify the student's understanding of the basic concepts, but also to illustrate the way speci®c structural changes in¯uence mechanism and reactivity. The ®rst three chapters discuss fundamental bonding theory, stereochemistry, and conformation, respectively. Chapter 4discusses the means of study and description of reaction mechanisms. Chapter 9 focuses on aromaticity and aromatic stabilization and can be used at an earlier stage of a course if an instructor desires to do so. The other chapters discuss speci®c mechanistic types, including nucleophilic substitution, polar additions and eliminations, carbon acids and enolates, carbonyl chemistry, aromaticsubstitution, concerted reactions, free-radical reactions, and photochemistry. Both the language of valence bond theory and of molecular orbital theory are used in discussing structural effects on reactivity and mechanism. Our intent is to illustrate both approaches to interpretation. A decade has passed since the publication of the Third Edition. That decade has seen signi®cant developments in areascovered by the text. Perhaps most noteworthy has been the application of computational methods to a much wider range of problems of structure and mechanism. We have updated the description of computational methods and have included examples throughout the text of application of computational methods to speci®c reactions. References to the primary literature are provided for speci®c issues of structure,reactivity, and mechanism. These have been chosen to illustrate the topic of discussion and, of course, cannot be comprehensive. The examples and references chosen do not imply any priority of concept or publication. References to general reviews which can provide a broader coverage of the various topics are usually given. The problems at the end of each chapter represent application of conceptsto new structures and circumstances, rather than review of material explicitly presented in the text. The level of dif®culty is similar to that of earlier editions, and we expect that many will present a considerable challenge to students. Some new problems have been added in this

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PREFACE TO THE FOURTH EDITION

edition. References to the literature material upon which the problemsare based are given at the end of the book. The companion volume, Part B, has also been revised to re¯ect the continuing development of synthetic methodology. Part B emphasizes synthetic application of organic reactions. We believe that the material in Part A and Part B will provide advanced undergraduate and beginning graduate students with a background which will permit them to understand,...