Organic Chemistry

2607 Pages·2018·65.035 MB·English

by  Janice Gorzynski Smith

Page i

Organic Chemistry
Sixth Edition
Janice Gorzynski Smith
University of Hawai'i at Mānoa
Page ii
ORGANIC CHEMISTRY, SIXTH EDITION
Published by McGraw-Hill Education, 2 Penn Plaza, New York, NY 10121. Copyright © 2020 by
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Library of Congress Cataloging-in-Publication Data
Names: Smith, Janice G., author.
Title: Organic chemistry / Janice Gorzynski Smith, University of Hawai'i at Mānoa.
Description: Sixth edition. | New York, NY : McGraw-Hill Education, [2020] | Includes index.
Identifiers: LCCN 2018032811 | ISBN 9781260119107 (alk. paper) |
 ISBN 1260119106 (alk. paper)
Subjects: LCSH: Chemistry, Organic—Textbooks.
Classification: LCC QD253.2 .S63 2020 | DDC 547—dc23 LC record available at
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Page iii
About the Author
©Daniel C. Smith
Janice Gorzynski Smith was born in Schenectady, New York. She received an A.B.
degree summa cum laude in chemistry from Cornell University, and a Ph.D. in Organic
Chemistry from Harvard University under the direction of Nobel Laureate E. J. Corey.
During her tenure with the Corey group, she completed the total synthesis of the plant
growth hormone gibberellic acid.
Following her postdoctoral work as a National Science Foundation National Needs
Postdoctoral Fellow at Harvard, Jan joined the faculty of Mount Holyoke College,
where she was employed for 21 years. During this time she was active in teaching
organic chemistry lecture and lab courses, conducting a research program in organic
synthesis, and serving as department chair. Her organic chemistry class was named
one of Mount Holyoke's “Don't-miss courses” in a survey by Boston magazine. After
spending two sabbaticals amidst the natural beauty and diversity in Hawai'i in the
1990s, Jan and her family moved there permanently in 2000. She is a faculty member
at the University of Hawai'i at Mānoa, where she teaches the two-semester organic
chemistry lecture and lab courses. In 2003, she received the Chancellor's Citation for
Meritorious Teaching.
Jan resides in Hawai'i with her husband Dan, an emergency medicine physician,
pictured with her in Antarctica in 2018. She has four children and six grandchildren.
When not teaching, writing, or enjoying her family, Jan bikes, hikes, snorkels, and
scuba dives in sunny Hawai'i, and time permitting, enjoys travel and Hawaiian
quilting.

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Contents in Brief
Prologue  1
1 Structure and Bonding  7
2 Acids and Bases  59
3 Introduction to Organic Molecules and Functional
Groups  93
4 Alkanes  131
5 Stereochemistry  179
6 Understanding Organic Reactions  222
7 Alkyl Halides and Nucleophilic Substitution  
256
8 Alkyl Halides and Elimination Reactions  308
9 Alcohols, Ethers, and Related Compounds  345
10 Alkenes and Addition Reactions  397
11 Alkynes and Synthesis  441
12 Oxidation and Reduction  472
Spectroscopy A Mass Spectrometry  512
Spectroscopy B Infrared Spectroscopy  534
Spectroscopy C Nuclear Magnetic Resonance Spectroscopy  562
13 Radical Reactions  611
14 Conjugation, Resonance, and Dienes  648
15 Benzene and Aromatic Compounds  689
16 Reactions of Aromatic Compounds  725
17 Introduction to Carbonyl Chemistry;
Organometallic Reagents; Oxidation and
Reduction  780
18 Aldehydes and Ketones—Nucleophilic Addition  
833
19 Carboxylic Acids and Nitriles  885
20 Carboxylic Acids and Their Derivatives—
Nucleophilic Acyl Substitution  926
21 Substitution Reactions of Carbonyl Compounds at
the α Carbon  973
22 Carbonyl Condensation Reactions  1011
23 Amines  1047
24 Carbon–Carbon Bond-Forming Reactions in
Organic Synthesis  1102
25 Pericyclic Reactions  1131
26 Carbohydrates  1162
27 Amino Acids and Proteins  1212
28 Synthetic Polymers  1259
29 Lipids  1292 (Available online)
Appendices  A
Glossary  G
Index  I-1