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MECHANISM -$$.NDTHmw -INORGANIC -CHEMISTRY &$*+?% . m-- ,t: 2 , Ihomas H.Lowry Kathleen SchuelierRichardson , ,.> . MECHANISM AND THEORY ORGANIC CHEMISTRY THOMAS H. LOWRY Smith College and KATHLEEN SCHUELLER RICHARDSON The Ohio State University HARPER & ROW,PUBLISHERS New York, Hagerstown, San Francisco, London To Nancy and Frank Sponsoring Editor: John A. Woods Special Projects Editor: Carol J. Dempster Project Editor: Brenda Goldberg Designer: T. R. Funderburk Production Supervisor: Will C. Jomarrbn Compositor: William Clowes & Sons Limited Printer and Binder: Halliday Lithograph Corporation Art Studio: Vantage Art Inc. Copyright 0 1976 by Thomas H. Lowry and Kathleen Schueller Richardson All rights reserved. Printed in the United States of America. No part of this book may be used or reproduced in any manner whatsoever without written permission except in the case of brief quotations embodied in critical articles and reviews. For information address Harper & Row, Publishers, Inc., 10 East 53rd Street, New York, N. Y. 10022. Library of Congress Cataloging in Publication Data Lowry, Thomas H. Mechanism and theory in organic chemistry. Includes bibliographical references and index. 1. Chemistry. Physical organic. I. Richardson, Kathleen Schueller,joint author. 11. Title. QD476.1A68 547'. 1'3 75-43926 ISBN 0-06-044082-1 CONTENTS Preface ix 1 - THE COVALENT BOND 1 1.1 1.2 1.3 1.4 1.5 MODELS OF CHEMICAL BONDING1 MOLECULAR ORBITALS9 HYBRIDORBITALS20 DELOCALIZED P BONDING27 AROMATICITY 28 PROBLEMS40 Appendix 1: Hybrid Orbitals 43 Appendix 2: Molecular Orbital Theory 50 2 SOME FUNDAMENTALS OF PHYSICAL ORGANIC CHEMISTRY 57 2.1 2.2 2.3 2.4 2.5 2.6 2.7 STEREOCHEMISTRY