Organic Synthesis
- 5th Edition - August 13, 2024
- Imprint: Academic Press
- Author: Michael Smith
- Language: English
- Paperback ISBN:9 7 8 - 0 - 4 4 3 - 1 5 8 6 7 - 4
- eBook ISBN:9 7 8 - 0 - 4 4 3 - 1 5 8 6 8 - 1
**2025 Textbook and Academic Authors Association (TAA) Textbook Excellence "Texty" Award Winner**Organic Synthesis, Fifth Edition provides a reaction-based approach to… Read more
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Request a sales quote**2025 Textbook and Academic Authors Association (TAA) Textbook Excellence "Texty" Award Winner**
Organic Synthesis, Fifth Edition provides a reaction-based approach to this important branch of organic chemistry. Updated and accessible, this eagerly-awaited revision offers a comprehensive foundation for graduate students coming from disparate backgrounds and knowledge levels, providing them with critical working knowledge of basic reactions, stereochemistry, and conformational principles. This reliable resource uniquely incorporates molecular modeling content, problems, and visualizations, and includes reaction examples and homework problems drawn from the latest in the current literature.
There have been advancements in organic reactions, particularly organometallic reactions, and there is a need to show how these advancements have influenced current organic synthesis. The goal is to revise and update the reaction examples taken from the synthesis literature from 2017 to 2023. The reactions illustrate those used most often in modern organic synthesis, but these new examples will show their current relevance. Where new approaches and reactions have been developed for organic synthesis, examples have been added as new material.
- Provides new content, reaction examples, and study problems from recent research
- Features improved organization, new art, and new chapter content on process chemistry and green organic chemistry
- Includes revised homework for each chapter, with new examples and questions
Graduate students in Organic Chemistry, undergraduate Chemistry majors in advanced undergraduate courses, Organic Chemists working in the pharmaceutical industry
- Cover image
- Title page
- Table of Contents
- Copyright
- About the Author
- Preface to the Fifth Edition
- 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
- 1.6 CONCLUSION
- HOMEWORK
- CHAPTER 2. Acids and Bases and Addition Reactions
- 2.1 Introduction
- 2.2 BRØNSTED-LOWRY ACIDS AND BASES
- 2.3 LEWIS ACIDS
- 2.4 HARD-SOFT ACID-BASE THEORY
- 2.5 ACID-BASE REACTIONS OF ALKENES AND ALKYNES (ADDITION REACTIONS)
- 2.6 CONCLUSION
- HOMEWORK
- CHAPTER 3. Functional Group Exchange Reactions: Aliphatic and Aromatic Substitution and Elimination Reactions
- 3.1 INTRODUCTION
- 3.2 ALIPHATIC SUBSTITUTION REACTIONS
- 3.3 HETEROATOM-STABILIZED CARBOCATIONS
- 3.4 SUBSTITUTION BY HALOGEN
- 3.5 AROMATIC SUBSTITUTION
- 3.6 ELIMINATION REACTIONS
- 3.7 CHARACTERISTICS OF SUBSTITUTION AND ELIMINATION REACTIONS
- 3.8 SYN-ELIMINATION REACTIONS
- 3.9 1,3-ELIMINATION (DECARBOXYLATION)
- 3.10 1,3-ELIMINATION (GROB FRAGMENTATION)
- 3.11 CONCLUSION
- HOMEWORK
- CHAPTER 4. Acids, Bases, and Functional Group Exchange Reactions: Acyl Addition and Acyl Substitution
- 4.1 INTRODUCTION
- 4.2 REACTIONS OF CARBONYL COMPOUNDS
- 4.3 NUCLEOPHILIC ACYL ADDITION TO ALDEHYDES AND KETONES
- 4.4 NUCLEOPHILIC ACYL SUBSTITUTION OF ACID DERIVATIVES
- 4.5 CONJUGATE ADDITION
- 4.6 FUNCTIONAL GROUP MANIPULATION BY REARRANGEMENT
- 4.7 MACROCYCLIC COMPOUNDS
- 4.8 CONCLUSION
- HOMEWORK
- CHAPTER 5. Functional Groups Exchange Reactions: Protecting Groups
- 5.1 INTRODUCTION
- 5.2 WHEN ARE PROTECTING GROUPS NEEDED?
- 5.3 PROTECTING GROUPS FOR ALCOHOLS, CARBONYLS, AND AMINES
- 5.4 CONCLUSION
- HOMEWORK
- CHAPTER 6. Functional Group Exchange Reactions: Oxidations
- 6.1 INTRODUCTION
- 6.2 ALCOHOLS TO CARBONYLS (CH—OH→C═O)
- 6.3 FORMATION OF PHENOLS AND QUINONES
- 6.4 OXIDATION OF ALKENES TO EPOXIDES
- 6.5 OXIDATION OF ALKENES TO DIOLS (C=C → CHOH-CHOH)
- 6.6 BAEYER-VILLIGER OXIDATION (RCOR’ → RCO2R’)
- 6.7 OXIDATIVE BOND CLEAVAGE (C═C → C═O + O═C)
- 6.8 OXIDATION OF ALKYL OR ALKENYL FRAGMENTS (CH → C=O or C—OH)
- 6.9 OXIDATION OF SULFUR, SELENIUM, AND NITROGEN
- 6.10 CONCLUSION
- HOMEWORK
- CHAPTER 7. Functional Group Exchange Reactions: Reductions
- 7.1 INTRODUCTION
- 7.2 THE NATURE OF HYDRIDE REDUCING AGENTS
- 7.3 BORANE AND ALUMINUM HYDRIDE
- 7.4 SODIUM BOROHYDRIDE
- 7.5 ALTERNATIVE METAL BOROHYDRIDES (Li, Zn, Ce)
- 7.6 LITHIUM ALUMINUM HYDRIDE
- 7.7 HYDRIDE REDUCING AGENTS WITH ELECTRON-RELEASING GROUPS
- 7.8 HYDRIDE REDUCING AGENTS WITH ELECTRON-WITHDRAWING GROUPS
- 7.9 STEREOSELECTIVITY IN REDUCTIONS
- 7.10 CATALYTIC HYDROGENATION
- 7.11 DISSOLVING METAL REDUCTIONS
- 7.12 NONMETALLIC REDUCING AGENTS
- 7.13 CONCLUSION
- HOMEWORK
- CHAPTER 8. Synthetic Strategies
- 8.1 INTRODUCTION
- 8.2 TARGET SELECTION
- 8.3 RETROSYNTHESIS
- 8.4 SYNTHETIC STRATEGIES
- 8.5 THE STRATEGIC BOND APPROACH
- 8.6 STRATEGIC BONDS IN RINGS
- 8.7 SELECTED SYNTHETIC STRATEGIES: MERRILACTONE A
- 8.8 BIOMIMETIC APPROACH TO RETROSYNTHESIS
- 8.9 THE CHIRAL TEMPLATE APPROACH
- 8.10 DEGRADATION TECHNIQUES AS A TOOL FOR RETROSYNTHESIS
- 8.11 COMPUTER-GENERATED STRATEGIES
- 8.12 CONCLUSION
- HOMEWORK
- Chapter 9. Functional Group Exchange Reactions: Hydroboration
- 9.1 INTRODUCTION
- 9.3 PREPARATION OF ALKENYLBORANES
- 9.4 FORMATION OF OXYGEN-CONTAINING FUNCTIONAL GROUPS
- 9.5 OTHER FUNCTIONAL GROUP EXCHANGE REACTIONS
- 9.6 CONCLUSION
- HOMEWORK
- CHAPTER 10. Functional Group Exchange Reactions: Selectivity
- 10.1 INTRODUCTION
- 10.2 STEREOCONTROL IN ACYCLIC SYSTEMS
- 10.3 STEREOCONTROL IN CYCLIC SYSTEMS
- 10.4 NEIGHBORING GROUP EFFECTS AND CHELATION EFFECTS
- 10.5 ACYCLIC STEREOCONTROL VIA CYCLIC PRECURSORS
- 10.6 BALDWIN’S RULES FOR RING CLOSURE
- 10.7 CONCLUSION
- HOMEWORK
- CHAPTER 11. Carbon-Carbon Bond-Forming Reactions: Cyanide, Alkyne Anions, Grignard Reagents, and Organolithium Reagents
- 11.1 INTRODUCTION
- 11.2 CYANIDE
- 11.3 ALKYNE ANIONS (R-C≡C:−)
- 11.4 GRIGNARD REAGENTS (C—Mg)
- 11.5 GRIGNARD REAGENTS: REDUCTION, ORGANOCERIUM REAGENTS, AND ENOLIZATION
- 11.6 ORGANOLITHIUM REAGENTS (C—Li)
- 11.7 CONCLUSION
- HOMEWORK
- CHAPTER 12. Carbon-Carbon Bond-Forming Reactions: Stabilized Carbanions and Ylids
- 12.1 INTRODUCTION
- 12.2 SULFUR-STABILIZED CARBANIONS AND UMPOLUNG
- 12.3 ORGANOCOPPER REAGENTS (C—Cu)
- 12.4 PHENOLIC CARBANIONS
- 12.5 YLIDS
- 12.6 TRANSITION METAL OLEFINATION REAGENTS
- 12.7 SILANE REAGENTS
- 12.8 CONCLUSION
- HOMEWORK
- CHAPTER 13. Nucleophilic Species That Form Carbon-Carbon Bonds: Enolate Anions
- 13.1 INTRODUCTION
- 13.2 FORMATION OF ENOLATE ANIONS
- 13.3 REACTIONS OF ENOLATE ANIONS WITH ELECTROPHILES
- 13.4 ENOLATE CONDENSATION REACTIONS
- 13.5 STEREOSELECTIVE ENOLATE REACTIONS
- 13.6 ENAMINES
- 13.7 MICHAEL ADDITION AND RELATED REACTIONS
- 13.8 ENOLATE REACTIONS OF α-HALO CARBONYL DERIVATIVES
- 13.9 CONCLUSION
- HOMEWORK
- CHAPTER 14. Pericyclic Reactions: The Diels-Alder Reaction
- 14.1 INTRODUCTION
- 14.2 FRONTIER MOLECULAR ORBITAL THEORY
- 14.3 HOMO AND LUMO ENERGIES AND ORBITAL COEFFICIENTS
- 14.4 ALLOWED AND FORBIDDEN REACTIONS
- 14.5 [4 + 2]-CYCLOADDITIONS
- 14.6 RATE ENHANCEMENT IN DIELS-ALDER REACTIONS
- 14.7 INTRAMOLECULAR DIELS-ALDER REACTIONS
- 14.8 INVERSE ELECTRON DEMAND AND THE RETRO-DIELS-ALDER REACTIONS
- 14.9 HETEROATOM DIELS-ALDER REACTIONS
- 14.10 ENANTIOSELECTIVE DIELS-ALDER REACTIONS
- 14.11 ENZYMATIC DIELS-ALDER REACTIONS
- 14.12 CONCLUSION
- HOMEWORK
- CHAPTER 15. Pericyclic Reactions: [m+n]-Cycloadditions, Sigmatropic Rearrangements, Electrocyclic, and Ene Reactions
- 15.1 INTRODUCTION
- 15.2 [2+2]-CYCLOADDITION REACTIONS
- 15.3 ELECTROCYCLIC REACTIONS
- 15.4 [3+2]-CYCLOADDITION REACTIONS
- 15.5 Other Cycloaddition Reactions
- 15.6 SIGMATROPIC REARRANGEMENTS
- 15.7 THE ENE REACTION
- 15.8 CONCLUSION
- HOMEWORK
- CHAPTER 16. Carbon-Carbon Bond-Forming Reactions: Carbocation and Oxocarbenium Ion Intermediates
- 16.1 INTRODUCTION
- 16.2 CARBOCATIONS
- 16.3 CARBOCATIONS AND CARBON-CARBON BOND-FORMING REACTIONS
- 16.4 FRIEDEL–CRAFTS REACTIONS
- 16.5 FRIEDEL–CRAFTS REACTIONS: FORMATION OF HETEROATOM-CONTAINING DERIVATIVES
- 16.6 CONCLUSION
- HOMEWORK
- Chapter 17. Formation of Carbon-Carbon Bonds via Radicals and Carbenes
- 17.1 INTRODUCTION
- 17.2 STRUCTURE OF RADICALS
- 17.3 FORMATION OF RADICALS BY THERMOLYSIS
- 17.4 PHOTOCHEMICAL FORMATION OF RADICALS
- 17.5 REACTIONS OF FREE RADICALS
- 17.6 INTERMOLECULAR RADICAL REACTIONS
- 17.7 INTRAMOLECULAR RADICAL REACTIONS (RADICAL CYCLIZATION)
- 17.8 METAL-INDUCED RADICAL REACTIONS
- 17.9 CARBENES AND CARBENOIDS
- 17.10 CONCLUSION
- HOMEWORK
- CHAPTER 18. Metal-Mediated, Carbon-Carbon Bond-Forming Reactions
- 18.1 INTRODUCTION
- 18.2 COPPER-CATALYZED COUPLING REACTIONS
- 18.3 π-ALLYL PALLADIUM COMPLEXES
- 18.4 NAMED PALLADIUM-CATALYZED COUPLING REACTIONS
- 18.5 π-ALLYL NICKEL COMPLEXES
- 18.6 METATHESIS REACTIONS
- 18.7 PAUSON-KHAND REACTION
- 18.8 ORGANOMETALLIC COMPOUNDS AS CARBANIONIC REAGENTS
- 18.9 ELECTROPHILIC IRON COMPLEXES
- 18.10 CONCLUSION
- HOMEWORK
- CHAPTER 19. Combinatorial and Process Chemistry and Flow Synthesis
- 19.1 COMBINATORIAL CHEMISTRY
- 19.2 PROCESS CHEMISTRY
- 19.3 CONTINUOUS FLOW SYNTHESIS
- 19.4 CONCLUSION
- HOMEWORK
- Subject Index
- Disconnection Index
- Edition: 5
- Published: August 13, 2024
- Imprint: Academic Press
- No. of pages: 1144
- Language: English
- Paperback ISBN: 9780443158674
- eBook ISBN: 9780443158681
MS
Michael Smith
Professor Michael B. Smith received an A.A. from Ferrum College in 1967 and a BS in chemistry from Virginia Polytechnic Institute in 1969. After working for 3 years at the Newport News Shipbuilding and Dry Dock Co. in New- port News VA as an analytical chemist, he entered graduate school at Purdue University. He received a PhD in Organic Chemistry in 1977. He spent 1 year as a faculty research associate at the Arizona State University with Professor G. Robert Pettit, working on the isolation of cytotoxic principles from plants and sponges. He spent a second year of postdoctoral work with Professor Sidney M. Hecht at the Massachusetts Insti- tute of Technology, working on the synthesis of bleomycin A2.
Smith began his academic career at the University of Connecticut in 1979, where he is currently professor of chemistry. In addition to this research, he is the author of the fifth, sixth, and seventh editions of March’s Advanced Organic Chemistry. He is also the author of an undergraduate textbook in organic chemistry titled Organic Chemistry. An Acid-Base Approach, now in its second edition. He is the editor of the Compendium of Organic Synthetic Methods, Volumes 6–13. He is the author of Organic Chemistry: Two Semesters, in its second edition, which is an outline of undergraduate organic chemistry to be used as a study guide for the first organic course. He has authored a research monograph titled Synthesis of Non-alpha Amino Acids, in its second edition.
Affiliations and expertise
Department of Chemistry, University of Connecticut, USARead Organic Synthesis on ScienceDirect