,Organic Chemistry
Seventh Edition
Janice Gorzynski Smith
University of Hawai‘i at Mānoa
,ORGANIC CHEMISTRY, SEVENTH EDITION
Published by McGraw Hill LLC, 1325 Avenue of the Americas, New York, NY 10019. Copyright ©2024
by McGraw Hill LLC. All rights reserved. Printed in the United States of America. Previous editions
©2020, 2017, and 2014. No part of this publication may be reproduced or distributed in any form or by any
means, or stored in a database or retrieval system, without the prior written consent of McGraw Hill LLC,
including, but not limited to, in any network or other electronic storage or transmission, or broadcast for
distance learning.
Some ancillaries, including electronic and print components, may not be available to customers outside the
United States.
This book is printed on acid-free paper.
1 2 3 4 5 6 7 8 9 LWI 28 27 26 25 24 23
ISBN 978-1-264-14153-1 (bound edition)
MHID 1-264-14153-X (bound edition)
ISBN 978-1-266-67876-9 (loose-leaf edition)
MHID 1-266-67876-X (loose-leaf edition)
Portfolio Manager: Ian Townsend
Product Developer: Mary E. Hurley
Marketing Manager: Cassie Cloutier
Content Project Managers: Jane Mohr and Rachael Hillebrand
Manufacturing Project Manager: Sandy Ludovissy
Content Licensing Specialist: Lorraine Buczek
Cover Image: Ethan Daniels/Stocktrek Images, Inc./Alamy Stock Photo
Compositor: Aptara, Inc.
All credits appearing on page or at the end of the book are considered to be an extension of the copyright page.
Library of Congress Cataloging-in-Publication Data
Names: Smith, Janice Gorzynski, author.
Title: Organic chemistry/Janice Gorzynski Smith, University of Hawaii at
Mānoa.
Description: Seventh edition. | New York, NY: McGraw Hill Education, [2024] |
Includes index.
Identifiers: LCCN 2022021540 (print) | LCCN 2022021541 (ebook) |
ISBN 9781264141531 (hardcover) | ISBN 9781266678769 (spiral bound) |
ISBN 9781266670114 (ebook) | ISBN 9781266681516 (ebook other)
Subjects: LCSH: Chemistry, Organic—Textbooks.
Classification: LCC QD253.2.S63 2024 (print) | LCC QD253.2 (ebook) |
DDC 547—dc23/eng/20220906
LC record available at https://lccn.loc.gov/2022021540
LC ebook record available at https://lccn.loc.gov/2022021541
The Internet addresses listed in the text were accurate at the time of publication. The inclusion of a website
does not indicate an endorsement by the author or McGraw Hill LLC, and McGraw Hill LLC does not
guarantee the accuracy of the information presented at these sites.
mheducation.com/highered
, About the Author
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 Chem-
istry 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, 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
Daniel C. Smith
department chair. Her organic chemistry class was named one of Mount Holyoke’s “Don’t-miss
courses” in a survey by Boston magazine. Jan and her family moved to Hawai‘i in 2000, and
she became a faculty member at the University of Hawai‘i at Mānoa. 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 the Galápagos Islands in 2021. She has four children and nine 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.
or Megan Sarah
iii
Seventh Edition
Janice Gorzynski Smith
University of Hawai‘i at Mānoa
,ORGANIC CHEMISTRY, SEVENTH EDITION
Published by McGraw Hill LLC, 1325 Avenue of the Americas, New York, NY 10019. Copyright ©2024
by McGraw Hill LLC. All rights reserved. Printed in the United States of America. Previous editions
©2020, 2017, and 2014. No part of this publication may be reproduced or distributed in any form or by any
means, or stored in a database or retrieval system, without the prior written consent of McGraw Hill LLC,
including, but not limited to, in any network or other electronic storage or transmission, or broadcast for
distance learning.
Some ancillaries, including electronic and print components, may not be available to customers outside the
United States.
This book is printed on acid-free paper.
1 2 3 4 5 6 7 8 9 LWI 28 27 26 25 24 23
ISBN 978-1-264-14153-1 (bound edition)
MHID 1-264-14153-X (bound edition)
ISBN 978-1-266-67876-9 (loose-leaf edition)
MHID 1-266-67876-X (loose-leaf edition)
Portfolio Manager: Ian Townsend
Product Developer: Mary E. Hurley
Marketing Manager: Cassie Cloutier
Content Project Managers: Jane Mohr and Rachael Hillebrand
Manufacturing Project Manager: Sandy Ludovissy
Content Licensing Specialist: Lorraine Buczek
Cover Image: Ethan Daniels/Stocktrek Images, Inc./Alamy Stock Photo
Compositor: Aptara, Inc.
All credits appearing on page or at the end of the book are considered to be an extension of the copyright page.
Library of Congress Cataloging-in-Publication Data
Names: Smith, Janice Gorzynski, author.
Title: Organic chemistry/Janice Gorzynski Smith, University of Hawaii at
Mānoa.
Description: Seventh edition. | New York, NY: McGraw Hill Education, [2024] |
Includes index.
Identifiers: LCCN 2022021540 (print) | LCCN 2022021541 (ebook) |
ISBN 9781264141531 (hardcover) | ISBN 9781266678769 (spiral bound) |
ISBN 9781266670114 (ebook) | ISBN 9781266681516 (ebook other)
Subjects: LCSH: Chemistry, Organic—Textbooks.
Classification: LCC QD253.2.S63 2024 (print) | LCC QD253.2 (ebook) |
DDC 547—dc23/eng/20220906
LC record available at https://lccn.loc.gov/2022021540
LC ebook record available at https://lccn.loc.gov/2022021541
The Internet addresses listed in the text were accurate at the time of publication. The inclusion of a website
does not indicate an endorsement by the author or McGraw Hill LLC, and McGraw Hill LLC does not
guarantee the accuracy of the information presented at these sites.
mheducation.com/highered
, About the Author
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 Chem-
istry 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, 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
Daniel C. Smith
department chair. Her organic chemistry class was named one of Mount Holyoke’s “Don’t-miss
courses” in a survey by Boston magazine. Jan and her family moved to Hawai‘i in 2000, and
she became a faculty member at the University of Hawai‘i at Mānoa. 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 the Galápagos Islands in 2021. She has four children and nine 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.
or Megan Sarah
iii