Organic Synthesis

3rd Edition

Print ISBN: 9781890661403
eBook ISBN: 9780124158849
Imprint: Academic Press
Published Date: 12th July 2011
Page Count: 1534
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A reactions oriented course is a staple of most graduate organic programs, and synthesis is taught either as a part of that course or as a special topic. Ideally, the incoming student is an organic major, who has a good working knowledge of basic reactions, stereochemistry and conformational principles. In fact, however, many (often most) of the students in a first year graduate level organic course have deficiencies in their undergraduate work, are not organic majors and are not synthetically inclined.

To save students much time catching up this text provides a reliable and readily available source for background material that will enable all graduate students to reach the same high level of proficiency in organic chemistry. Produced over many years with extensive feedback from students taking an organic chemistry course this book provides a reaction based approach. The first two chapters provide an introduction to functional groups; these are followed by chapters reviewing basic organic transformations (e.g. oxidation, reduction). The book then looks at carbon-carbon bond formation reactions and ways to ‘disconnect’ a bigger molecule into simpler building blocks.

Most chapters include an extensive list of questions to test the reader’s understanding. There is also a new chapter outlining full retrosynthetic analyses of complex molecules which highlights common problems made by scientists.

The book is intended for graduate and postgraduate students, scientific researchers in chemistry

Table of Contents

About the Author

Preface to the 3rd edition

Preface to the 1st edition. Why I wrote this book

Introducing SpartanModel


Common Abbreviations

Chapter 1. Retrosynthesis, Stereochemistry, and Conformations

1.1 Introduction

1.2 The Disconnection Protocol

1.3 Bond Proximity and Implications for Chemical Reactions

1.4 Stereochemistry

1.5 Conformations



Chapter 2. Acids, Bases and Functional Group Exchange Reactions

2.1 Introduction

2.2 Brønsted-Lowry Acids and Bases

2.3 Lewis Acids

2.4 Hard-Soft Acid-Base Theory41, 42

2.5 Acyl Addition, Substitution and Conjugate Addition

2.6 Substitution Reactions

2.7 Characteristics of Reactions Involving Nucleophiles

2.8 Substitution by Halogen

2.9 Elimination Reactions

2.10 Addition Reactions

2.11 Functional Group Manipulation byRearrangement

2.12 Aromatic Substitution

2.13 Conclusion


Chapter 3. Oxidation

3.1 Introduction

3.2 Alcohols to Carbonyls (CH-OH → C=O)

3.3 Formation of Phenols and Quinones

3.4 Conversion of Alkenes to Epoxides

3.5 Conversion of Alkenes to Diols (C=C → CHOH-CHOH)

3.6 Baeyer-Villiger Oxidation (RC0R’ → RC02R’)

3.7 Oxidative Bond Cleavage (C=C → C=O + O=C)

3.8 Oxidation of Alkyl or Alkenyl Fragments (CH → C=O OR C-OH)

3.9 Oxidation of Sulfur, Selenium, and Nitrogen

3.10 Conclusion


Chapter 4. Reduction

4.1 Introduction

4.2 Reduction with Complex Metal Hydrides

4.3 Alkoxyaluminate Reagents

4.4 Reductions with Borohydride120

4.5 Alkoxy- and Alkylborohydrides

4.6 Borane, Aluminum Hydride, and Derivatives

4.7 Stereoselectivity in Reductions

4.8 Catalytic Hydrogenation



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"Smith (Univ. of Connecticut) has geared this book to graduate-level course in organic synthesis, and he reinforces material in each chapter with relevant homework problems. The third edition (2nd ed., 2001; 1st ed., 1994) includes more than 600 new reactions and 900 new references, compared to the second edition. These reactions and references are all new since 2002, clearly illustrating the field’s continuing growth. Another key addition is the integration of synthesis-related molecular modeling problems using SpartanModel into the homework problems. The extensive index allows the reader to easily find specific information. Coverage of the topic is thorough, with very little wasted space on any of the 1,506 pages…. Summing Up: Recommended. Upper-division undergraduates through professionals/practitioners."--CHOICE

"This is without doubt a must-have organic chemistry textbook. It is clear, concise and very readable. Trying to write a textbook is extremely difficult and demanding, but trying to write one that is the superlative book in a student's, or practicing chemist's, library is an almost impossible task. Michael Smith has achieved that. From the very beginning you are immersed in the fundamentals of retrosynthesis, stereochemistry, oxidations, reductions and protecting group strategies. This is made complete by the thorough blend of theory and referenced examples from the literature. With a comprehensive toolkit of named organic reaction mechanisms to piece it all together, this is by far the all-in- one book for organic chemists. Organic Synthesis outshines the most popular organic chemistry books in my own collection and now takes its seat as my companion both in the lab and on my desk. I can wholeheartedly recommend this book to chemists at all stages of their career."--Chemistry World, June 2012, page 61