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Author:   Lewis ,  Lewis, Andrew
Publisher:   Oxford University Press Inc
Imprint:   Oxford University Press Inc
Dimensions:   Width: 21.60cm , Height: 3.80cm , Length: 27.90cm
Weight:   2.442kg
ISBN:  

9780199758975

ISBN 10:   0199758972
Pages:   1176
Publication Date:   15 September 2015
Audience:   College/higher education ,  Tertiary & Higher Education
Format:   Paperback
Publisher's Status:   Active
Availability:   To order  
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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:"

Reviews

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

Author Information

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

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