Jeffrey Elbert
University of Northern Iowa
INTRODUCTION TO
ORGANIC CHEMISTRY
Third Edition
William Brown
Beloit College
Thomas Poon
Claremont McKenna, Pitzer, and Scripps Colleges
John Wiley & Sons, Inc.
,To order books or for customer service call 1-800-CALL-WILEY (225-5945).
Copyright © 2005 by John Wiley & Sons, Inc.
Excerpts from this work may be reproduced by instructors
for distribution on a not-for-profit basis for testing or
instructional purposes only to students enrolled in courses
for which the textbook has been adopted. Any other
reproduction or translation of this work beyond that
permitted by Sections 107 or 108 of the 1976 United States
Copyright Act without the permission of the copyright
owner is unlawful. Requests for permission or further
information should be addressed to the Permissions
Department, John Wiley & Sons, Inc., 111 River Street,
Hoboken, NJ 07030.
ISBN 0-471-68692-1
Printed in the United States of America
10 9 8 7 6 5 4 3 2 1
Printed and bound by Malloy Lithographing, Inc.
, CONTENTS
CHAPTER 1. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1
CHAPTER 2. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 12
CHAPTER 3. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 24
CHAPTER 4. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 36
CHAPTER 5. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 48
CHAPTER 6. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 61
CHAPTER 7. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 75
CHAPTER 8. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 88
CHAPTER 9. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 100
CHAPTER 10. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 116
CHAPTER 11. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 130
CHAPTER 12. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 138
CHAPTER 13. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 148
CHAPTER 14. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 161
CHAPTER 15. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 176
CHAPTER 16. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 191
CHAPTER 17. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 207
CHAPTER 18. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 221
CHAPTER 19. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 235
CHAPTER 20. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 247
CHAPTER 21. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 258
CHAPTER 22. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 271
,