Química Organica

RESEARCH TECHNIQUES IN ORGANIC CHEMISTRY

Robert B. Bates
Department of Chemistry University of Arizona

John P. Schaefer
Dean, College of Liberal Arts University of Arizona

PRENTICE-HALL,

INC.,

E N G L E W O O D

CLIFFS, N . J

©

1971 by Prentice-Hall, Inc. Englewood Cliffs, N.J.

All rights reserved. No part of this book may be reproduced in any form or by any meanswithout permission in writing from the publisher.

C—13-774489-7 P _ l 3-774471 -4 Library of Congress Catalog Card Number 74-14041 1 Printed in the United States of America

PRENTICE-HALL INTERNATIONAL, INC., London PRENTICE-HALL OF AUSTRALIA, PTY. LTD., Sydney PRENTICE-HALL OF CANADA, LTD., Toronto PRENTICE-HALL OF INDIA PRIVATE LIMITED, New Delhi PRENTICE-HALL OF JAPAN, INC., Tokyo

10

9Current Printing (last digit): 8 7 6 5 4 3 2 1

To our wives

Foreword
Organic chemistry today is a rapidly changing subject whose almost frenetic activity is attested by the countless research papers appearing in established and new journals and by the proliferation of monographs and reviews on all aspects of the field. This expansion of knowledge poses pedagogical problems; it isdifficult for a single organic chemist to be cognizant of developments over the whole field and probably no one or pair of chemists can honestly claim expertise or even competence in all the important areas of the subject. Yet the same rapid expansion of knowledge—in theoretical organic chemistry, in stereochemistry, in reaction mechanisms, in complex organic structures, in the application of physicalmethods—provides a remarkable opportunity for the teacher of organic chemistry to present the subject as it really is, an active field of research in which new answers are currently being sought and found. To take advantage of recent developments in organic chemistry and to provide an authoritative treatment of the subject at an undergraduate level, the Foundations of Modern Organic ChemistrySeries has been established. The series consists of a number of short, authoritative books, each written at an elementary level but in depth by an organic chemistry teacher active in research and familiar with the subject of the volume. Most of the authors have published research papers in the fields on which they are writing. The books will present the topics according to current knowledge of thefield, and individual volumes will be revised as often as necessary to take account of subsequent developments. The basic organization of the series is according to reaction type, rather than along the more classical lines of compound class. The first ten volumes in the series constitute a core of the material covered in nearly every one-year organic chemistry course. Of these ten, the first threeare a general introduction to organic chemistry and provide a background for the next six, which deal with specific types of reactions and may be covered in any order. Each of the reaction types is presented from an elementary viewpoint, but in a depth not possible in conventional textbooks. The teacher can decide how much of a volume to cover. The tenth examines the problem of organic synthesis,employing and tying together the reactions previously studied. The remaining volumes provide for the enormous flexibility of the series. These cover topics which are important to students of organic
vii

chemistry and are sometimes treated in the first organic course, sometimes in an intermediate course. Some teachers will wish to cover a number of these books in the one-year course; otherswill wish to assign some of them as outside reading; a complete intermediate organic course could be based on the eight "topics" texts taken together. The series approach to undergraduate organic chemistry offers then the considerable advantage of an authoritative treatment by teachers active in research, of frequent revision of the most active areas, of a treatment in depth of the most fundamental...