Part B: Reactions and Synthesis
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FOURTH EDITION
Part B: Reactions and Synthesis
Advanced Organic Chemistry PART A: Structure and Mechanisms PART B: Reactions and Synthesis
Advanced Organic • t ry FOURTH ChemlS EDITION Part B: Reactions and Synthesis FRANCIS A. CAREY and RICHARD J. SUNDBERG
University of Virginia Charlottesville, Virginia
~Springer
Library of Congress Cataloging-in-Publication Data Carey, Francis A., 1937Advanced organic chemistry/Francis A. Carey and Richard J. Sundberg.-4th ed. p. em. Includes bibliographical references and index. Contents: pt. B. Reactions and synthesis I. Sundberg, Richard J., 1938- II. Title. QD251.2 .C36 2000 547-dc21 00-059652
Library of Congress Cataloging-in-Publication Data Carey, Francis A., 1937Advanced organic chemistry/Francis A. Carey and Richard ). Sundberg.-4th ed. p.cm. Includes bibliographical references and index. Contents: pt. B. Reactions and synthesis I. Sundberg, Richard)., 1938- II. Title. QD251.2 .C36 2000 547-dc21
00-059652
A C.I.P. record for this book is available from the Library of Congress
ISBN 978-3-662-38652-1
ISBN 978-3-662-39510-3 (eBook)
DOI 10.1007/978-3-662-39510-3 © 2001,1990,1984,1977 Springer Science+ Business Media New York Originally published by Springer Science Business Media, Inc. in 2001 All rights reserved. No part of this book may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, microfilming, recording, or otherwise, without written permission from the Publisher. (Springer Science+Business Media, LLC). The front cover shows the key orbital interactions in the Diels-Alder reaction. The highest-occupied molecular orbital (HOMO) of 1,3-butadiene and the lowest-unoccupied molecular orbital (LUMO) of ethylene overlap in phase with one another allowing the reaction to occur in a single step. 10 9 8 7 6 5 4 3 springeronline.com
Preface to the Fourth Edition Part B emphasizes the most important reactions used in organic synthesis. The material is organized by reaction type. Chapters 1 and 2 discuss the alkylation, conjugate addition and carbonyl addition/condensation reactions of enolates and other carbon nucleophiles. Chapter 3 covers the use of nucleophilic substitution, both at saturated carbon and at carbonyl groups, in functional group of interconversions. Chapter 4 discusses electrophilic additions to alkenes and alkynes, including hydroboration. Chapter 5 discusses reduction reactions, emphasizing alkene and carbonyl-group reductions. Concerted reactions, especially Diels-Alder and other cycloadditions and sigmatropic rearrangements, are considered in Chapter 6. Chapters 7, 8, and 9 cover organometallic reagents and intermediates in synthesis. The main-group elements lithium and magnesium as well as zinc are covered in Chapter 7. Chapter 8 deals with the transition metals, especially copper, palladium, and nickel. Chapter 9 discusses synthetic reactions involving boranes, silanes, and stannanes. Synthetic reactions which involve highly reactive intermediates-carbocations, car
