Organic Synthesis

Organic Synthesis, 3rd Edition

Organic Synthesis, 3rd Edition,Michael Smith,ISBN9781890661403


Academic Press




A synthesis-based approach to learning and teaching organic reactions.

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Key Features

    • New publisher, new edition; extensively updated and corrected
    • Over 950 new references with more than 6100 references in total
    • Over 600 new reactions and figures replaced or updated
    • Over 300 new homework problems from the current literature to provide nearly 800 problems to test reader understanding of the key principles
    • Free molecular modeling software to explore 60 new synthesis-oriented molecular modeling problems; designed to aid visualisation and understanding of organic synthesis


    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


    advanced undergraduates, post graduates, postdocs in organic chemistry and organic synthesis

    Michael Smith

    Professor of Chemistry, University of Connecticut, USA

    Affiliations and Expertise

    Department of Chemistry, University of Connecticut, USA

    Organic Synthesis, 3rd Edition

    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

    4.9 Dissolving Metal Reductions




    Chapter 5. Hydroboration

    5.1 Introduction

    5.2 Preparation of Alkyl and Alkenyl Boranes

    5.3 Synthetic Transformations

    5.4 Formation of Oxygen-Containing Functional Groups

    5.5 Amines and Sulfides VIA Hydroboration

    5.6 Conclusion


    Chapter 6. Stereocontrol and Ring Formation

    6.1 Introduction

    6.2 Stereocontrol in Acyclic Systems

    6.3 Stereocontrol in CyclIc Systems

    6.4 Neighboring Group Effects and Chelation Effects

    6.5 Acyclic Stereocontrol Via Cyclic Precursors

    6.6 Ring-Forming Reactions

    6.7 Conclusion


    Chapter 7. Protecting Groups

    7.1 Introduction

    7.2 When are Protecting Groups Needed?

    7.3 Protecting Groups for Alcohols, Carbonyls, and Amines

    7.4 Conclusion


    Chapter 8. C Disconnect Products

    8.1 Introduction

    8.2 Cyanide

    8.3 Alkyne Anions (R–C≡C:–)

    8.4 Grignard Reagents (C-MG)

    8.5 Organolithium Reagents (C-Li)

    8.6 Sulfur Stabilized Carbanions and Umpolung

    8.7 Organocopper Reagents (C-Cu)

    8.8 Ylids

    8.9 Other Organometallic Carbanionic Compounds

    8.10 Allylic Tin, Alkyltitanium, and Allylic Silane Complexes

    8.11 Phenolic Carbanions

    8.12 Conclusion


    Chapter 9. C Disconnect Products

    9.1 Introduction

    9.2 Formation of Enolate Anions

    9.3 Reactions of Enolate Anions with Electrophiles

    9.4 Enolate Condensation Reactions

    9.5 Stereoselective Enolate Reactions

    9.6 Enamines

    9.7 Michael Addition and Related Reactions

    9.8 Enolate Reactions of α-Halo Carbonyl Derivatives

    9.9 Conclusion


    Chapter 10. Synthetic Strategies

    10.1 Introduction

    10.2 Target Selection

    10.3 Retrosynthesis

    10.4 Synthetic Strategies62

    10.5 The Strategic Bond Approach

    10.6 Strategic Bonds in Rings

    10.7 Selected Synthetic Strategies: Pancratistatin

    10.8 Biomimetic Approach to Retrosynthesis

    10.9 The Chiral Template Approach

    10.10 Computer Generated Strategies

    10.11 Degradation Techniques as a Tool for Retrosynthesis

    10.12 Combinatorial Chemistry

    10.13 Conclusion


    Chapter 11. Pericyclic carbon-carbon Bond Forming reactions

    11.1 Introduction

    11.2 Frontier molecular orbital theory

    11.3 Allowed and Forbidden Reactions

    11.4 [4 + 2]-Cycloadditions

    11.5 Inverse Electron Demand and the Retro Diels-Alder

    11.6 Rate Enhancement In Diels-Alder Reactions

    11.7 Heteroatom Diels-Alder Reactions

    11.8 Intramolecular Diels-Alder Reactions233

    11.9 Enantioselective Diels-Alder Reactions

    11.10 [2+2]-Cycloaddition Reactions

    11.11 Electrocyclic Reactions

    11.12 [3+2]-Cycloaddition Reactions

    11.13 Sigmatropic Rearrangements

    11.14 The Ene Reaction

    11.15 Conclusion


    Chapter 12. C Disconnect Products

    12.1 Introduction

    12.2 Carbocations

    12.3 Carbon-Carbon Bond Forming Reactions of Carbocations

    12.4 Friedel-Crafts Reactions

    12.5 Friedel-Crafts Reactions: Formation of Heteroatom-Containing Derivatives

    12.6 π-Allyl Palladium Complexes

    12.7 Named Palladium Coupling Reactions

    12.8 π-Allyl Nickel Complexes

    12.9 Electrophilic Iron Complexes

    12.10 Conclusion


    Chapter 13. Carbon Radical Disconnect Products

    13.1 Introduction

    13.2 Structure of Radicals

    13.3 Formation of Radicals by Thermolysis

    13.4 Photochemical Formation of Radicals

    13.5 Reactions of Free Radicals

    13.6 Intermolecular Radical Reactions

    13.7 Intramolecular Radical Reactions (Radical Cyclization)

    13.8 Metal-Induced Radical Reactions

    13.9 Carbenes and Carbenoids

    13.10 Metathesis Reactions

    13.11 Pauson-Khand Reaction

    13.12 Conclusion


    Chapter 14. Student Synthesis: The First Synthetic Problem

    14.1 Introduction

    14.2 Total Synthesis of Securamine C


    14.3 Total Synthesis of Variecolol

    Disconnection Index


    Quotes and reviews

    "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

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