186,99 €
Mehr erfahren.
- Herausgeber: John Wiley & Sons
- Kategorie: Wissenschaft und neue Technologien
- Sprache: Englisch
Leading reference on the theories of organic chemistry, now updated to reflect the most recent literature from 2018 to 2023
Building on the success of the 8th Edition as winner of the Textbook & Academic Authors Association 2021 McGuffey Longevity Award, the revised and updated 9th Edition of March’s Advanced Organic Chemistryexplains the theories of organic chemistry, covers new advances in areas of organic chemistry published between 2018 and 2023, and guides readers to plan and execute multi-step synthetic reactions. Detailed examples and descriptions of all reactions are included throughout the text.
As in previous editions, the goal of this edition is to give equal weight to three fundamental aspects of the study of organic chemistry: reactions, mechanisms, and structure. Specific but specialized areas of organic chemistry, such as terpenes, polymerization, and steroids, have been incorporated into primary sections rather than segregated into their own sections.
The first nine chapters cover general organic chemistry with theoretical principles. The next 10 chapters address reactions and mechanistic discussion. Appendix A focuses on literature references and resources. More than 4,400 references are included throughout the text.
March’s Advanced Organic Chemistry provides information on:
- Localized and delocalized chemical bonding and bonding weaker than covalent
- Microwave chemistry, use of ultrasound, mechanochemistry, and reactions done under flow conditions
- Acids and bases, irradiation processes, stereochemistry, structure of intermediates, and ordinary and photochemical reactions
- Mechanisms and methods of determining carbocations, carbanions, free radicals, carbenes, and nitrenes
- Aliphatic, alkenyl, and alkynyl substitution, additions to carbon-carbon and carbon-hetero bonds, eliminations, rearrangements, and oxidations and reductions
This 9th Edition of March’s Advanced Organic Chemistry continues to serve as a must-have reference for every student and professional working in organic chemistry or related fields.
Sie lesen das E-Book in den Legimi-Apps auf:
Seitenzahl: 5602
Veröffentlichungsjahr: 2025
Ähnliche
MARCH'S ADVANCED ORGANIC CHEMISTRY
REACTIONS, MECHANISMS, AND STRUCTURE
NINTH EDITION
Michael B. Smith
Professor Emeritus
University of Connecticut
Department of Chemistry
Willington, CT, USA
Copyright © 2025 by John Wiley & Sons Inc. All rights reserved, including rights for text and data mining and training of artificial technologies or similar technologies.
Published by John Wiley & Sons, Inc., Hoboken, New Jersey.Published simultaneously in Canada.
No part of this publication may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, recording, scanning, or otherwise, except as permitted under Section 107 or 108 of the 1976 United States Copyright Act, without either the prior written permission of the Publisher, orauthorization through payment of the appropriate per‐copy fee to the Copyright Clearance Center, Inc., 222 Rosewood Drive, Danvers, MA 01923, (978) 750‐8400, fax (978) 750‐4470, or on the web at www.copyright.com. Requests to the Publisher for permission should be addressed to the Permissions Department, John Wiley & Sons, Inc., 111 River Street, Hoboken, NJ 07030, (201) 748‐6011, fax (201) 748‐6008, or online at http://www.wiley.com/go/permission.
The manufacturer’s authorized representative according to the EU General Product Safety Regulation is Wiley‐VCH GmbH, Boschstr. 12, 69469 Weinheim, Germany, e‐mail: [email protected].
Trademarks: Wiley and the Wiley logo are trademarks or registered trademarks of John Wiley & Sons, Inc. and/or its affiliates in the United States and other countries and may not be used without written permission. All other trademarks are the property of their respective owners. John Wiley & Sons, Inc. is not associated with any product or vendor mentioned in this book.
Limit of Liability/Disclaimer of Warranty: While the publisher and author have used their best efforts in preparing this book, they make no representations or warranties with respect to the accuracy or completeness of the contents of this book and specifically disclaim any implied warranties of merchantability or fitness for a particular purpose. No warranty may be created or extended by sales representatives or written sales materials. The advice and strategies contained herein may not be suitable for your situation. You should consult with a professional where appropriate. Neither the publisher nor author shall be liable for any loss of profit or any other commercial damages, including but not limited to special, incidental, consequential, or other damages. Further, readers should be aware that websites listed in this work may have changed or disappeared between when this work was written and when it is read. Neither the publisher nor authors shall be liable for any loss of profit or any other commercial damages, including but not limited to special, incidental, consequential, or other damages.
For general information on our other products and services or for technical support, please contact our Customer Care Department within the United States at (800) 762‐2974, outside the United States at (317) 572‐3993 or fax (317) 572‐4002.
Wiley also publishes its books in a variety of electronic formats. Some content that appears in print may not be available in electronic formats. For more information about Wiley products, visit our website at www.wiley.com.
Library of Congress Cataloging‐in‐Publication DataName: Smith, Michael B., author.Title: March’s advanced organic chemistry : reactions, mechanisms, and structure / Michael B. Smith, Department of Chemistry, University of Connecticut, Willington, CT, USA.Description: Ninth edition. | Hoboken, New Jersey : Wiley, [2025] | Includes index.Identifiers: LCCN 2024047187 (print) | LCCN 2024047188 (ebook) | ISBN 9781394242993 (cloth) | ISBN 9781394243013 (adobe pdf) | ISBN 9781394243020 (epub)Subjects: LCSH: Chemistry, Organic.Classification: LCC QD251.2 .M37 2025 (print) | LCC QD251.2 (ebook) | DDC 547–dc23/eng/20241226LC record available at https://lccn.loc.gov/2024047187LC ebook record available at https://lccn.loc.gov/2024047188
Cover Design: WileyCover Images: Courtesy of Michael B. Smith
NEW REACTION SECTIONS CORRELATION: 8TH EDITION → 9TH EDITION
8TH → 9TH
10‐1 → 10‐1
10‐2 → 10‐1
10‐3 → 10‐1
10‐4 → 10‐2
10‐5 → 10‐3
10‐6 → 10‐3
10‐7 → 10‐4
10‐8 → 10‐5
10‐9 → 10‐6
10‐10 → 10‐7
10‐11 → 10‐8
10‐12 → 10‐9
10‐13 → 10‐10
10‐14 → 10‐11
10‐15 → 10‐9
10‐16 → 10‐12
10‐17 → 10‐13
10‐18 → 10‐14
10‐19 → 16‐62
New → 10‐15
New → 10‐16
10‐20 → 10‐17
10‐21 → 10‐18
10‐22 → 10‐19
10‐23 → 10‐20
New → 10‐21
10‐24 → 10‐22
10‐25 → 10‐23
10‐26 → 10‐24
10‐27 → 10‐25
10‐28 → 10‐26
10‐29 → 10‐27
10‐30 → 10‐28
10‐31 → 10‐29
10‐32 → 10‐30
10‐33 → 10‐31
10‐34 → 10‐32
10‐35 → 10‐33
10‐36 → 10‐32
10‐37 → 10‐34
10‐38 → 10‐35
10‐39 → 10‐36
10‐40 → 10‐37
10‐41 → 10‐38
10‐42 → 10‐39
10‐43 → 10‐40
10‐44 → 10‐41
10‐45 → 10‐42
10‐46 → 10‐43
10‐47 → 10‐44
10‐48 → 10‐45
New → 10‐46
10‐49 → 10‐47
10‐50 → 10‐48
10‐51 → 10‐49
10‐52 → 10‐50
10‐53 → 10‐51
10‐54 → 10‐52
10‐55 → 10‐53
10‐56 → 10‐54
10‐57 → 10‐55
10‐58 → 10‐56
10‐59 → 10‐57
10‐60 → 10‐58
10‐61 → 10‐59
10‐62 → 10‐59
10‐63 → 10‐60
10‐64 → 10‐61
10‐65 → 10‐62
10‐66 → 10‐63
10‐67 → 10‐64
New → 10‐65
10‐68 → 10‐66
10‐69 → 10‐67
10‐70 → 10‐68
10‐71 → 10‐69
10‐72 → 10‐70
10‐73 → 10‐71
10‐74 → 10‐72
10‐75 → 10‐73
10‐76 → 10‐74
10‐77 → 10‐75
10‐78 → 10‐76
11‐1 → 11‐1
11‐2 → 11‐2
11‐3 → 11‐3
11‐4 → 11‐6
11‐5 → 11‐4
11‐6 → 11‐5
11‐7 → 11‐7
11‐8 → 11‐7
11‐9 → 11‐7
11‐10 → 11‐8
11‐11 → 11‐9
11‐12 → 11‐15
11‐13 → 11‐14
11‐14 → 11‐16
11‐15 → 11‐10
11‐16 → 11‐11
11‐17 → 11‐12
11‐18 → 11‐13
11‐19 → 11‐17
11‐20 → 11‐18
11‐21 → 11‐19
11‐22 → 11‐20
11‐23 → 11‐21
11‐24 → 11‐22
11‐25 → 11‐23
11‐26 → 11‐24
11‐27 → 11‐25
11‐28 → 11‐26
11‐29 → 11‐27
11‐30 → 11‐28
11‐31 → 11‐29
11‐32 → 11‐30
11‐33 → 11‐31
11‐34 → 11‐32
11‐35 → 11‐33
11‐36 → 11‐34
11‐37 → 11‐35
11‐38 → 11‐36
12‐1 → 12‐1
12‐2 → 15‐1
12‐3 → 12‐2
12‐4 → 12‐3
12‐5 → 12‐4
12‐6 → 12‐5
12‐7 → 12‐6
12‐8 → 12‐7
12‐9 → 12‐8
12‐10 → 12‐9
12‐11 → 12‐9
12‐12 → 12‐10
12‐13 → 12‐11
12‐14 → 12‐12
12‐15 → 12‐13
12‐16 → 12‐14
12‐17 → 12‐15
12‐18 → 12‐16
12‐19 → 12‐17
12‐20 → 12‐18
12‐21 → 12‐19
12‐22 → 12‐20
12‐23 → 12‐20
12‐24 → 12‐21
12‐25 → 12‐22
12‐26 → 12‐22
12‐27 → 12‐23
12‐28 → Deleted
12‐29 → 12‐24
12‐30 → 12‐25
12‐31 → 12‐26
12‐32 → 12‐27
12‐33 → 12‐28
12‐34 → 12‐29
12‐35 → 12‐29
12‐36 → 12‐29
12‐37 → 12‐30
12‐38 → 12‐20
12‐39 → 12‐31
12‐40 → 12‐32
12‐41 → 12‐33
12‐42 → 12‐34
12‐43 → 12‐35
12‐44 → 12‐35
12‐45 → 12‐35
12‐46 → 12‐36
12‐47 → 12‐37
12‐48 → 12‐38
12‐49 → 12‐39
12‐50 → 12‐40
12‐51 → 12‐41
12‐52 → 12‐42
13‐1 → 13‐1
13‐2 → 13‐2
13‐3 → 13‐3
13‐4 → 13‐4
13‐5 → 13‐5
13‐6 → 13‐6
13‐7 → 13‐8
13‐8 → 13‐9
New → 13‐10
13‐9 → 13‐11
13‐10 → 13‐11
13‐11 → 13‐11
13‐12 → 13‐12
13‐13 → 13‐13
13‐14 → 13‐14
13‐15 → 13‐15
13‐16 → 13‐16
13‐17 → 13‐17
13‐18 → 13‐18
13‐19 → 13‐19
13‐20 → 13‐1
13‐21 → 13‐20
13‐22 → 13‐7
13‐23 → 13‐21
13‐24 → 13‐22
13‐25 → Deleted
13‐26 → 13‐23
13‐27 → 13‐13
13‐28 → 13‐11
13‐29 → 13‐24
13‐30 → 13‐25
13‐31 → 13‐26
13‐32 → 13‐27
13‐33 → 13‐28
13‐34 → 13‐29
14‐1 → 14‐1
14‐2 → 14‐2
14‐3 → 14‐1
14‐4 → 14‐3
14‐5 → 14‐4
14‐6 → 14‐5
14‐7 → 14‐6
14‐8 → 14‐7
14‐9 → 14‐8
14‐10 → 14‐9
14‐11 → 14‐10
14‐12 → 14‐11
14‐13 → 14‐12
14‐14 → 14‐13
14‐15 → 14‐14
14‐16 → 14‐15
14‐17 → 14‐16
14‐18 → 14‐17
14‐19 → 14‐18
14‐20 → 14‐19
14‐21 → 14‐20
14‐22 → 14‐21
14‐23 → 14‐22
14‐24 → 14‐23
14‐25 → 14‐24
14‐26 → 14‐25
15‐1 → 15‐1
15‐2 → 15‐2
15‐3 → 15‐3
15‐4 → 15‐4
15‐5 → 15‐5
15‐6 → 15‐6
15‐7 → 15‐7
15‐8 → 15‐8
15‐9 → 15‐9
15‐10 → 15‐10
15‐11 → 15‐11
15‐12 → 15‐12
15‐13 → 15‐14
15‐14 → 15‐19
15‐15 → 15‐15
15‐16 → 15‐13
15‐17 → 15‐13
15‐18 → 15‐16
15‐19 → 15‐20
15‐20 → 15‐21
15‐21 → 15‐21
15‐22 → 15‐25
15‐23 → 15‐23
15‐24 → 15‐21
15‐25 → 15‐17
15‐26 → 15‐18
15‐27 → 15‐22
15‐28 → 15‐26
15‐29 → 15‐27
15‐30 → 15‐28
15‐31 → 15‐29
15‐32 → 15‐29
15‐33 → 15‐29
15‐34 → 15‐30
15‐35 → 15‐31
15‐36 → 15‐32
15‐37 → 15‐33
15‐38 → 15‐34
15‐39 → 15‐35
15‐40 → 15‐36
15‐41 → 15‐37
15‐42 → 15‐38
15‐43 → 15‐39
15‐44 → 15‐40
15‐45 → 15‐41
15‐46 → 15‐42
15‐47 → 15‐43
15‐48 → 15‐44
15‐49 → 15‐45
15‐50 → 15‐46
15‐51 → 15‐47
15‐52 → 15‐48
15‐53 → 15‐49
15‐54 → 15‐51
15‐55 → 15‐52
15‐56 → 15‐53
15‐57 → 15‐54
15‐58 → 15‐55
15‐59 → 15‐50
15‐60 → 15‐24
15‐61 → 15‐56
15‐62 → 15‐57
16‐1 → 16‐1
16‐2 → 16‐2
16‐3 → 16‐3
16‐4 → 16‐4
16‐5 → 16‐5
16‐6 → 16‐6
16‐7 → 16‐7
16‐8 → 16‐8
16‐9 → 16‐9
16‐10 → 16‐10
16‐11 → 16‐11
16‐12 → 16‐12
16‐13 → 16‐13
16‐14 → 16‐14
16‐15 → 16‐15
16‐16 → 16‐16
16‐17 → 16‐15
16‐18 → 16‐17
16‐19 → 16‐18
16‐20 → 16‐19
16‐21 → 16‐20
16‐22 → 16‐21
16‐23 → 16‐21
16‐24 → 16‐23
16‐25 → 16‐24
16‐26 → 16‐25
16‐27 → 16‐26
16‐28 → 16‐22
16‐29 → 16‐22
16‐30 → 16‐27
16‐31 → 16‐28
16‐32 → 16‐29
16‐33 → 16‐30
16‐34 → 16‐31
16‐35 → 16‐32
16‐36 → 16‐33
16‐37 → 16‐34
16‐38 → 16‐35
16‐39 → 16‐35
16‐40 → 16‐36
16‐41 → 16‐37
16‐42 → 16‐38
16‐43 → 16‐39
16‐44 → 16‐40
16‐45 → 16‐40
16‐46 → 16‐41
16‐47 → 16‐42
16‐48 → 16‐43
16‐49 → 16‐44
16‐50 → 16‐45
16‐51 → 16‐46
16‐52 → 16‐47
16‐53 → 16‐48
16‐54 → 16‐49
16‐55 → 16‐50
16‐56 → 16‐51
16‐57 → 16‐52
16‐58 → 16‐53
16‐59 → 16‐54
16‐60 → 16‐55
16‐61 → 16‐56
16‐62 → 16‐57
16‐63 → 16‐58
16‐64 → 16‐59
16‐65 → 16‐60
16‐66 → 16‐61
16‐67 → 16‐62
16‐68 → 16‐63
16‐69 → 16‐64
16‐70 → 16‐65
16‐71 → 16‐66
16‐72 → 16‐67
16‐73 → 16‐68
16‐74 → 16‐69
16‐75 → 16‐70
16‐76 → 16‐71
16‐77 → 16‐72
16‐78 → 16‐73
16‐79 → 16‐74
16‐80 → 16‐75
16‐81 → 16‐76
16‐82 → 16‐77
16‐83 → 16‐78
16‐84 → 16‐79
16‐85 → 16‐80
16‐86 → 16‐81
16‐87 → 16‐82
16‐88 → 16‐83
16‐89 → 16‐84
16‐90 → 16‐85
16‐91 → 16‐86
16‐92 → 16‐87
16‐93 → 16‐88
16‐94 → 16‐89
16‐95 → 16‐90
16‐96 → 16‐91
16‐97 → 16‐92
16‐98 → 16‐93
17‐1 → 17‐1
17‐2 → 17‐2
17‐3 → 17‐3
17‐4 → 17‐4
17‐5 → 17‐5
17‐6 → 17‐6
17‐7 → 17‐7
17‐8 → 17‐8
17‐9 → 17‐9
17‐10 → 17‐10
17‐11 → 17‐11
17‐12 → 17‐12
17‐13 → 17‐13
17‐14 → 17‐14
17‐15 → 17‐15
17‐16 → 17‐16
17‐17 → 17‐17
17‐18 → 17‐18
17‐19 → 17‐19
17‐20 → 17‐20
17‐21 → 17‐21
17‐22 → 17‐22
17‐23 → 17‐23
17‐24 → 17‐24
17‐25 → 17‐25
17‐26 → 17‐26
17‐27 → 17‐27
17‐28 → 17‐28
17‐29 → 17‐29
17‐30 → 17‐30
17‐31 → 17‐31
17‐32 → 17‐32
17‐33 → 17‐33
17‐34 → 17‐34
17‐35 → 17‐35
17‐36 → 17‐36
18‐1 → 18‐1
18‐2 → 18‐2
18‐3 → 18‐3
18‐4 → 18‐4
18‐5 → 18‐5
18‐6 → 18‐6
18‐7 → 18‐7
18‐8 → 18‐8
18‐9 → 18‐9
18‐10 → 18‐10
18‐11 → 18‐11
18‐12 → 18‐12
18‐13 → 18‐13
18‐14 → 18‐14
18‐15 → 18‐15
18‐16 → 18‐16
18‐17 → 18‐17
18‐18 → 18‐18
18‐19 → 18‐19
18‐20 → 18‐20
18‐21 → 18‐21
18‐22 → 18‐22
18‐23 → 18‐23
18‐24 → 18‐23
18‐25 → 18‐24
18‐26 → 18‐25
18‐27 → 18‐26
18‐28 → 18‐27
18‐29 → 18‐28
18‐30 → 18‐29
18‐31 → 18‐30
18‐32 → 18‐31
18‐33 → 18‐32
18‐34 → 18‐33
18‐35 → 18‐34
18‐36 → 18‐35
18‐37 → 18‐36
18‐38 → 18‐37
18‐39 → 18‐38
18‐40 → 18‐39
18‐41 → 18‐40
18‐42 → 18‐41
18‐43 → 18‐42
18‐44 → 18‐43
19‐1 → 19‐1
19‐2 → 19‐2
19‐3 → 19‐3
19‐4 → 19‐4
19‐5 → 19‐5
19‐6 → 19‐6
19‐7 → 19‐7
19‐8 → 19‐8
19‐9 → 19‐9
19‐10 → 19‐10
19‐11 → 19‐11
19‐12 → 19‐12
19‐13 → 19‐13
19‐14 → 19‐14
19‐15 → 19‐14
19‐16 → 19‐14
19‐17 → 19‐16
19‐18 → 19‐15
19‐19 → 19‐15
19‐20 → 19‐17
19‐21 → 19‐18
19‐22 → 19‐19
19‐23 → 19‐20
19‐24 → 19‐21
19‐25 → 19‐22
19‐26 → 19‐23
19‐27 → 19‐24
19‐28 → 19‐24
19‐29 → 19‐25
19‐30 → 19‐25
19‐31 → 19‐26
19‐32 → 19‐27
19‐33 → 19‐25
19‐34 → 19‐28
19‐35 → 19‐29
19‐36 → 19‐30
19‐37 → 19‐31
19‐38 → 19‐32
19‐39 → 19‐33
19‐40 → 19‐34
19‐41 → 19‐35
19‐42 → 19‐35
19‐43 → 19‐36
19‐44 → 19‐36
19‐45 → 19‐36
19‐46 → 19‐37
19‐47 → 19‐38
19‐48 → 19‐38
19‐49 → 19‐39
19‐50 → 19‐39
19‐51 → 19‐40
19‐52 → 19‐41
19‐53 → 19‐42
19‐54 → 19‐43
19‐55 → 19‐44
19‐56 → 19‐45
19‐57 → 19‐46
19‐58 → 19‐46
19‐59 → 19‐47
19‐60 → 19‐47
19‐61 → 19‐48
19‐62 → 19‐48
19‐63 → 19‐48
19‐64 → 19‐49
19‐65 → 19‐50
19‐66 → 19‐51
19‐67 → 19‐52
19‐68 → 19‐53
19‐69 → 19‐54
19‐70 → 19‐55
19‐71 → 19‐56
19‐72 → 19‐57
19‐73 → 19‐58
19‐74 → 19‐59
19‐75 → 19‐60
19‐76 → 19‐60
19‐77 → 19‐61
19‐78 → 19‐57
19‐79 → 19‐60
19‐80 → 19‐62
19‐81 → 19‐63
19‐82 → 19‐64
19‐83 → 19‐65
19‐84 → 19‐65
19‐85 → 19‐66
19‐86 → 19‐67
19‐87 → 19‐68
19‐88 → 19‐69
PREFACE
This ninth edition of March's Advanced Organic Chemistry has been thoroughly updated to include new advances in areas of organic chemistry published between 2018 and 2023. Every topic retained from the eighth edition has been brought up to date if there was activity in that area during that six‐year period. Changes include a significant rewrite of most of the book. More than 4400 new references have been added for work published since 2018. As with the eighth edition, many older references have been deleted to make room for new ones, and in cases where a series of papers by the same principal author were cited, all but the most recent were deleted. Older citations are usually found by referring to the more recent publication(s). It is noted that 31 journals were examined for this edition, but with this amount of available literature, it is inevitable that some work was not included. Indeed, the number of new papers in some areas makes it impossible to include all the research.
The fundamental structure of the ninth edition is essentially the same as that of all previous ones. Many of the figures considered to be redundant or not very useful were deleted for the this edition and several sections were consolidated. A correlation table of the sections in the eighth edition and their placement in the eighth and the ninth editions is provided above.
The goal, as in previous editions, is to give equal weight to three fundamental aspects of the study of organic chemistry: reactions, mechanisms, and structure. References are provided, and every effort has been given to provide a snapshot of current research. Specific but specialized areas of organic chemistry, terpenes, carbohydrates, proteins, many organometallic reagents, combinatorial chemistry, polymerization and electrochemical reactions, steroids, etc., have been incorporated into myriad pertinent sections rather than segregated into their own sections.
This book is largely directed at graduate students in their first year of study and to undergraduates advanced in their studies, but as with previous editions it is an off‐the‐shelf reference book. It is hoped that this book will lead a student to consult the many excellent books and review articles cited for the various topics to understand the subject in more detail. Indeed, most of these topics are so vast they cannot be explained completely in this book.
Chapters 1–5 (Part I) provide the background that is necessary for understanding mechanisms, but is important. The discussion begins with chemical bonding (Chapter 1) and there is a chapter on stereochemistry (Chapter 4). Chapter 5 discusses the structure of intermediates. Following Chapters 1–5, Chapters 6 and 7 address reaction mechanisms in general, one for ordinary reactions and the other for photochemical reactions. Other methods related to reactions are included in Chapter 7, including microwave chemistry, the use of ultrasound, mechanochemistry, and reactions done under flow conditions. Part I concludes with Chapters 8 and 9, which give further background to the study of mechanisms and reaction conditions.
The Part II introduction briefly describes how the second part of the book is organized. In the first part of each chapter the appropriate basic mechanisms are discussed along with considerations of reactivity and orientation, while the second part consists of numbered sections devoted to individual reaction types, where the scope and the mechanism of each reaction are discussed. The organization is based on reaction types, and a relatively few principles suffice to explain nearly all of them despite the large number of organic reactions. Accordingly, the reaction mechanisms section of this book (Part II) is divided into 10 chapters (10–19), each concerned with a different type of reaction. Numbered sections are used for the reactions and are set in boldface.
A correlation table is included after the table of contents that directly correlates the sections found in the ninth edition with the new ones in the eighth edition. It is important to note that the numbers for each reaction in the ninth edition are different from the eighth edition, as are changes in previous editions.
Although IUPAC has published the system for designating reaction mechanisms in earlier editions, all IUPAC designations for reactions found in previous editions have been removed in the ninth edition. These designations are not extensively used and many reactions were deemed by this author as difficult to categorize using only one designation.
In treating subjects as broad as structure, reactions, and mechanisms of organic chemistry, it is impossible to cover each topic in great depth, which would not be desirable even if possible. This book is intended to point the reader to the primary literature (the original journal publications). Secondary literatures sources, including reviews, books, and monographs, have been given as well. Appendix A provides a brief introduction to using modern computer‐based search engines such as Reaxys® and SciFinder®.
Although basically designed as a reference text for a one‐year course at graduate level, this book can also be used in advanced undergraduate courses but is most useful after completion of a one‐year course in organic chemistry. It has been my experience that students who have completed first‐year courses often have a hazy recollection of the material and greatly profit from a representation of the material if it is easily accessible. This book is probably most valuable as a reasonably up‐to‐date reference work. Students preparing for qualifying examinations and practicing organic chemists will find that Part II contains a survey of the mechanism and scope of a large number of reactions, arranged in an orderly manner based on reaction type and on which bonds are broken and formed.
For units of energy, IUPAC mandates kilojoules, and many journals do use this unit exclusively. Indeed, organic chemists who publish in United States journals commonly use kilocalories. Virtually all energy values are presented in both kilocalories and kilojoules. Although IUPAC does not recommend Ångstrom units (Å) for bond distances but rather picometers (pm), a vast number of bond distances published in the literature are in Ångstrom units, and this book therefore uses them.
I would like to acknowledge the contributions of those chemists cited and thanked by Professor March in the first four editions, and those I thanked in the fifth, sixth, seventh, and eighth editions. This book would not be possible without their contributions. I thank the many people who have contributed comments or have pointed out errors in editions five to eight, who were invaluable in putting together the ninth edition. I thank Warren Hehre and Sean Ohlinger of Wavefunction, Inc., Irvine, CA (www.wavefun.com) for providing Spartan 18 Macintosh (v. 1.4.8, 200921), which was used for the preparation of Spartan models for selected molecules and intermediates. All structures and line drawings in this book were done using ChemDraw® Professional 18.0.0.231 (4318), graciously provided by PerkinElmer Corporation, Waltham, MA.
Special thanks are due to the Interscience division of John Wiley & Sons and to Jonathan Rose. Special thanks are also given to Katherine Wong at Wiley and freelancer Lesley Montford for their fine work as editors in turning the manuscript into the finished book.
With gratitude, I acknowledge the pioneering work of the late Jerry March, upon whose work all the editions I have authored is built, although updates and changes have been made beginning with the fifth edition, However, Jerry is responsible for the concept and fundamental organization of this book and carried it through four very successful editions. I used the second and third editions of Jerry’s book as a student and it is an honor to continue this tradition.
I encourage those who read and use the ninth edition to contact me directly with comments and errors. I hope that this new edition will do justice to the tradition that Professor March began many years ago.
My email address is: [email protected]
Finally, I want to thank my wife Sarah for her patience and understanding during the preparation of this manuscript. Without her support, this work would not have been possible.
Michael B. Smith
Professor Emeritus
July, 2024
