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Advanced Organic Chemistry

David E. Lewis

Publication Date - September 2015

ISBN: 9780199758975

1176 pages
8-1/2 x 11 inches

In Stock

A true textbook for advanced organic chemistry courses


Written by a master teacher, Advanced Organic Chemistry presents a clear, concise, and complete overview of the subject that is ideal for both advanced undergraduate and graduate courses. In contrast with many other books, this volume is a true textbook, not a reference book.


* Uses a unique method of categorizing organic reactions that is based on reactivity principles rather than mechanism or functional group, enabling students to see reactivity patterns in superficially widely disparate systems

* Emphasizes fundamental physical organic concepts that reinforce themes, giving students the foundation to understand both mechanisms and synthesis

* Covers asymmetric methodologies, a topic that is now ubiquitous in the current literature

* Numerous in-chapter worked problems and end-of-chapter additional exercises allow students to apply concepts as they learn them

* More than 2500 references to the primary literature in the body of the book(along with another 750 references in the problems) encourage students to become familiar with real scholarship as they master the concepts

* Brief historical vignettes about relevant chemists
reinforce a historical and humanizing approach to learning science

About the Author(s)

David E. Lewis is Professor of Chemistry at the University of Wisconsin-Eau Claire.


"The content of Advanced Organic Chemistry is technically sound, the mechanistic details are accurate, and the material is current. The author has a very fluid writing style that is easy to read and is never boring. I would recommend this book to any instructors who teach advanced organic chemistry, physical organic chemistry, or organic synthesis."--Ihsan Erden, San Francisco State University

"Advanced Organic Chemistry is unique and without equal. Its modern focus and general coverage of all key areas of organic chemistry are amazing. This book could be of great use in an introductory graduate course like the one I teach, and also in advanced undergraduate courses in organic chemistry."--Scott Handy, Middle Tennessee State University

Table of Contents

    Chapter 1. The Fundamentals Revisited: Structure, Bonding, and Reactivity
    1.1 Organic Structure: A Brief History
    1.2 Proton Transfers Revisited: Acids and Bases
    1.3 Reactions and Reaction Mechanisms: "Electron Pushing"
    1.4 Resonance
    1.5 Spectroscopy and Chromatography
    Key Terms
    Additional Problems
    Chapter 2. Stereochemistry
    2.1 Stereoisomers and Chirality
    2.2 Absolute Configuration
    2.3 Optical Purity and Configuration
    2.4 Conformation
    2.5 An Introduction to Asymmetric Synthesis: Asymmetric Induction
    2.6 How Well Did It Go? Measuring Enantiomer Ratios
    2.7 Chirality at Atoms Other Than Carbon: Inversion of Pyramidal Centers
    Chapter Summary
    Key Terms
    Additional Problems
    Chapter 3. Organic Short-hand: Acronyms and Name Reactions
    3.1 Organic Synthesis: A Brief Introduction
    3.2 Name Reactions: A Historical Overview
    3.3 Acronyms and Abbreviations
    Chapter 4. Orbitals and Reactivity
    4.1 Introduction
    4.2 Atomic Orbitals: The History of the Modern Atomic Model
    4.3 Covalent Bonding and Molecular Orbitals
    4.4 Chemical Reactions: Frontier Orbitals
    Chapter Summary
    Key Terms
    Additional Problems
    Chapter 5. Frontier Orbitals and Chemical Reactions
    5.1 Using Frontier Orbitals (FMOs) to Categorize Reactions and Reagents
    5.2 Categorizing Reactions Using FMP Pairings
    5.3 Stereoelectronic Effects
    5.4 Radical Reactions
    Chapter Summary
    Key Terms
    Additional Problems
    Chapter 6. Synthetic Reactions I: Pericyclic Reactions and Conservation of Orbital Symmetry
    6.1 Introduction
    6.2 Molecular Orbitals of Conjugated Systems; Orbital Symmetry
    6.3 Qualitative Perturbation Theory: Approximating Frontier Orbitals of Substituted Alkenes and Dienes
    6.4 Sigmatropic Rearrangements
    6.5 Cycloaddition Reactions
    6.6 Ene, Retro-ene and Similar Reactions
    6.7 Combining Pericyclic Reactions in Sequence
    Chapter Summary
    Key Terms
    Reaction Synopses
    Additional Problems
    Chapter 7. Aromaticity
    7.1 Benzene: The Beginning
    7.2 Aromaticity and Antiaromaticity: The H:uckel Molecular Orbital Model of Cyclic Polyenes
    7.3 How Does One Measure Aromaticity? Criteria for Aromaticity and its Quantification
    7.4 M:obius Aromaticity
    7.5 Homoaromaticity
    7.6 The Rest of the Story . . . The History and Mythology of Benzene
    Chapter Summary
    Key Terms
    Additional Problems
    Chapter 8. Physical Organic Chemistry and Reaction Mechanisms
    8.1 Introduction
    8.2 Solvents and Solubility
    8.3 Reaction Kinetics
    8.4 Activation Parameters from Kinetic Studies
    8.5 Correlating Similar Reactions: Linear Free Energy Relationships
    8.6 Isotope and Element Effects
    8.7 Trapping and Crossover Experiments
    8.8 The Variable Transition State and the Concept of the Mechanistic Spectrum
    8.9 Using Regiochemistry and Stereochemistry
    8.10 The Reactivity-Selectivity Principle
    Chapter Summary
    Key Terms
    Additional Problems
    Chapter 9. Reactive Intermediates I: Carbocations
    9.1 Carbocations
    9.2 Rearrangements
    9.3 Neighboring Group Participation
    9.4 Non-classical Carbocations
    9.5 Methods for Generating Carbocations
    Chapter Summary
    Key Terms
    Reaction Synopses
    Additional Problems
    Chapter 10. Synthetic Reactions II: Using Carbocations for C--C Bond Formation in Synthesis
    10.1 Introduction
    10.2 The Friedel-Crafts Reaction
    10.3 Formylation
    10.4 Addition of Stabilized Cations to Alkenes: The Prins, Mannich, and Mukaiyama Reactions
    Chapter Summary
    Key Terms
    Reaction Synopses
    Additional Problems
    Chapter 11. Reactive Intermediates II: Carbanions and Their Reactivity
    11.1 Carbanions: Introduction and Overview
    11.2 Simple Organometallic Nucleophiles: Metal Alkyls
    11.3 Carbanions Stabilized by Heteroatoms
    11.4 Formation of Enolate Anions
    11.5 Rearrangements of Carbanions
    Chapter Summary
    Key Terms
    Reaction Synopses
    Additional Problems
    Chapter 12. Synthetic Reactions III: Synthetic Reactions of Carbon Nucleophiles, Part 1
    12.1 Carbon-Carbon Bond Formation: Carbon Nucleophiles and Electrophiles
    12.2 Substitution and Addition With Metal Alkyl Reagents Having C-M ? Bonds
    12.3 Metal Enolates: Versatile Carbon Nucleophiles
    12.4 The Aldol Addition Reaction
    12.5 Conjugate Addition of Enolates and Similar Compounds
    12.6 Azaenol Derivatives: Imines, Hydrazones and Enamines
    Chapter Summary
    Key Terms
    Reaction Synopses
    Additional Problems
    Chapter 13. Reactive Intermediates III: Free Radicals, Carbenes, Arynes and Nitrenes
    13.1 Free Radicals
    13.2 Carbenes
    13.3 Nitrenes
    13.4 Arynes
    Chapter Summary
    Key Terms
    Reaction Synopses
    Additional Problems
    Chapter 14. Synthetic Reactions IV: Applications of Free Radical Chemistry in Synthesis
    14.1 Methods for Site-Specific Generation of Free Radicals
    14.2 Reactions of Free Radicals
    14.3 Reactions of Free Radicals Useful for Synthesis
    14.4 Additions and Cyclizations of Free Radicals
    14.5 Diradicals: Formation and Uses in Synthesis
    Chapter Summary
    Key Terms
    Reaction Synopses
    Additional Problems
    Chapter 15. Organic Synthesis I: Retrosynthetic Analysis, Protecting Groups, and the Strategy of Organic Synthesis
    15.1 What is Organic Synthesis?
    15.2 Organic Reactions: Tools of the Organic Chemist
    15.3 Retrosynthetic Analysis: An Introduction to the Vocabulary and Strategy of Organic Synthesis
    15.4 Applying RetrosyntheticAnalysis to a Real Example
    15.5 Selectivity Revisited
    15.6 Protection of Alcohols
    15.7 Protection of Aldehydes, Ketones, and Carboxylic Acids
    15.8 Protection of Amines
    15.9 Protecting Groups for Hydrocarbons
    Chapter Summary
    Key Terms
    Reaction Synopses
    Additional Problems
    Chapter 16. Synthetic Reactions V: Condensations and Cascade Reactions of Carbon Nucleophiles
    16.1 Addition, Condensation, Cascade Reactions: Definitions
    16.2 The Aldol Condensation and Related Reactions
    16.3 Condensations Where the Initial Adduct is Intercepted
    16.4 The Claisen Condensation and Related Reactions
    16.5 The Wittig, Horner-Wadsworth-Emmons, and Related Reactions
    16.6 Cascade Reactions Initiated by Carbon Nucleophiles
    Chapter Summary
    Key Terms
    Reaction Synopses
    Additional Problems
    Chapter 17. Synthetic Reactions VI: Catalytic Reactions for C-C Bond Formation
    17.1 Catalysis and Green Chemistry
    17.2 Bonding in Organometallic Complexes
    17.3 Basic Organometallic Reactions: Reactions at the Metal
    17.4 Basic Organometallic Reactions: Reactions at the Ligand
    17.5 Hydrometalation: Making the Organometallic Reagents by Addition
    17.6 Palladium-Catalyzed Substitution: The Tsuji-Trost and Buchwald-Hartwig Reactions
    17.7 Cross-Coupling Reactions to Form C--C Bonds
    Chapter Summary
    Key Terms
    Reaction Synopses
    Additional Problems
    Chapter 18. Redox Reactions I: Oxidation
    18.1 Introduction
    18.2 Overview of Oxidation
    18.3 Oxidation of Alcohols to Aldehydes and Ketones with Stoichiometric Metal-Based Reagents
    18.4 Oxidation of Alcohols Using Non-Metal-Based Reagents
    18.5 Oxidations to Carboxylic Acids
    18.6 Oxidation of Ethers and Amines
    18.7 Oxidative Rearrangements
    18.8 Oxidation of Unsaturated Hydrocarbons
    18.9 Oxidative Cleavage of Carbon-Carbon Bonds
    18.10 Oxidative Substitution of Carbon-Hydrogen ? Bonds
    18.11 Oxidation of Alkanes
    18.12 A Catalogue of Oxidation Reactions: Oxidation at a Glance
    Chapter Summary
    Key Terms
    Reaction Synopses
    Additional Problems
    Chatper 19. Redox Reactions II: Reduction with Molecular Hydrogen or its Equivalent
    19.1 Overview of Reduction
    19.2 Catalytic Hydrogenation
    19.3 Hydrogenlysis
    Chapter Summary
    Key Terms
    Reaction Synopses
    Additional Problems
    Chapter 20. Redox III: Reduction with Complex Metal Hydrides and Active Metals
    20.1 Reductions with Metal Hydrides
    20.2 Reduction by Hydrogen Transfer from Carbon
    20.3 Stereochemistry and Stereoselectivity in Hydride Reduction
    20.4 Reduction Using Metals
    20.5 Reduction of Carbonyl Compounds to Hydrocarbons
    20.6 A Catalogue of Reduction Reactions: Reduction at a Glance
    Chapter Summary
    Key Terms
    Reaction Synopses
    Additional Problems
    Chapter 21. Aymmetric Oxidation and Reduction
    21.1 Asymmetric Redox Reactions: An Overview
    21.2 Sharpless Asymmetric Epoxidation of Allylic Alcohols
    21.3 Asymmetric Epoxidation of Unfunctionalized Alkenes
    21.4 Oxidation With Chiral Three-membered Heterocycles
    21.5 Asymmetric Dihydroxylation
    21.6 Kinetic Resolution of Alcohols
    21.7 Enantioselective Insertion into C--C and C--H Bonds
    21.8 Asymmetric Hydrogenation
    21.9 Asymmetric Reductions with Metal Hydrides and Metal Alkyls
    21.10 Enzymes: Biocatalysis of Redox Reactions
    Chapter Summary
    Key Terms
    Reaction Synopses
    Additional Problems
    Chapter 22. Main-Group Organic Chemistry: Silicon, Phosphorus, Sulfur, Selenium and Tin
    22.1 Introduction
    22.2 Silanes and Stannanes as Directing Groups: Carbocation Chemistry
    22.3 Heteroatom-Centered Nucleophiles: Silyllithiums, Stannyllithiums , Sulfides and Selenides
    22.4 Reactions of Organophosphorus, Organosulfur and Organoselenium Compounds
    Chapter Summary
    Key Terms
    Reaction Synopses
    Additional Problems
    Chapter 23. Modern Asymmetric Synthesis
    23.1 Controlling Absolute Stereochemistry
    23.2 Asymmetric Synthesis with Chiral Auxiliaries: Additions
    23.3 Asymmetric Substitution at Carbon: Alkylation of Enolates and Related Nucleophiles
    23.4 Catalytic Asymmetric Synthesis
    23.5 Representative Asymmetric Syntheses
    Chapter Summary
    Key Terms
    Additional Problems

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