Table of Contents

Chapter 1 Retrosynthesis, Stereochemistry, and Conformations 1

1.1. Introduction 0001

1.2. The disconnection protocol 0005

1.3. Bond proximity and implications for chemical reactions 0011

1.4. Stereochemistry 0012

1.5. Conformations 0035

1.6. Conclusion 0071

Homework 0072

Chapter 2 Acids, Bases and Functional Group Exchange Reactions 77

2.1. Introduction 0077

2.2. Brønsted-Lowry acids and bases 0081

2.3. Lewis acids 0093

2.4 Hard-Soft acid-base theory 0096

2.5. Acyl addition, substitution and conjugate addition 0106

2.6. Substitution reactions 0112

2.7. Characteristics of reactions involving nucleophiles 0137

2.8. Substitution by halogen 0144

2.9. Elimination reactions 0153

2.10. Addition reactions 0177

2.11. Functional group manipulation by rearrangement 0188

2.12. Aromatic substitution 0193

2.13. Conclusion 0210

Homework 0211

Chapter 3 Oxidation 219

3.1. Introduction 0219

3.2. Alcohols to carbonyls (CH–OH ¿ C=O) 0226

3.3. Formation of phenols and quinones 0261

3.4. Conversion of alkenes to epoxides 0268

3.5. Conversion of alkenes to diols (C=C ¿ CHOH–CHOH) 0291

3.6. Baeyer-Villiger oxidation RCOR' ¿ RCO2R') 0307

3.7. Oxidative bond cleavage (C=C ¿ C=O + O=C) 0313

3.8. Oxidation of alkyl or alkenyl fragments (CH ¿ C=O or C–OH) 0324

3.9. Oxidation of sulfur, selenium, and nitrogen 0334

3.10. Conclusion 0340

Homework 0340

Chapter 4 Reduction 347

4.1. Introduction 0347

4.2. Reduction with complex metal hydrides 0348

4.3. Alkoxyaluminate reagents 0363

4.4. Reductions with borohydride 0369

4.5. Alkoxy- and alkylborohydrides 0377

4.6. Borane, aluminum hydride, and derivatives 0385

4.7. Stereoselectivity in reducti


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Academic Press
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About the author

Michael Smith

Professor of Chemistry, University of Connecticut, USA

Affiliations and Expertise

Department of Chemistry, University of Connecticut, USA


"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