Organic Synthesis

Organic Synthesis

3rd Edition - July 12, 2011

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  • Author: Michael Smith
  • eBook ISBN: 9780124158849

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Description

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

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

    Readership

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

    Table of Contents

      • About the Author
      • Preface to the 3rd edition
      • Preface to the 1st edition. Why I wrote this book!
      • Available Separately: Introducing SpartanModel
        • Getting Started With SpartanModel
        • Problems Keyed to Organic Synthesis
        • Technical Overview of SpartanModel
      • Dedication
      • 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, 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 by Rearrangement
        • 2.12 Aromatic Substitution
        • 2.13 Conclusion
        • Homework
      • 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
        • HOMEWORK
      • 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
        • 4.10 NONMETALLIC REDUCING AGENTS
        • 4.11 CONCLUSION
        • HOMEWORK
      • 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
        • Homework
      • 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
        • Homework
      • 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
        • Homework
      • Chapter 8: Cd Disconnect Products: Nucleophilic Species that Form Carbon-Carbon Bonds
        • 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
        • Homework
      • Chapter 9: Cd Disconnect Products: Nucleophilic Species that Form Carbon-Carbon Bonds: Enolate Anions
        • 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
        • Homework
      • 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
        • Homework
      • Chapter 11: Pericyclic carbon-carbon Bond Forming reactions: Multiple Bond disconnections
        • 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
        • Homework
      • Chapter 12: Ca Disconnect Products: Electrophilic Carbon-Carbon Bond-Forming Reactions
        • 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
        • Homework
      • Chapter 13: Carbon Radical Disconnect Products: Formation of Carbon-Carbon Bonds via Radicals and Carbenes
        • 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
        • Homework
      • Chapter 14: Student Synthesis: The First Synthetic Problem
        • 14.1 Introduction
        • 14.2 Total Synthesis of Securamine C
        • 14.2.B The Critique
        • 14.3 Total Synthesis of Variecolol
        • 14.3.B The Critique
      • Disconnection Index
      • index

    Product details

    • No. of pages: 1534
    • Language: English
    • Copyright: © Academic Press 2011
    • Published: July 12, 2011
    • Imprint: Academic Press
    • eBook ISBN: 9780124158849

    About the Author

    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, USA

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