Advanced Organic Chemistry

Paperback | September 29, 2015

byDavid E. Lewis

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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.

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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.

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

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Format:PaperbackDimensions:1176 pages, 10.98 × 8.5 × 1.69 inPublished:September 29, 2015Publisher:Oxford University PressLanguage:English

The following ISBNs are associated with this title:

ISBN - 10:0199758972

ISBN - 13:9780199758975

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Table of Contents

1. The Fundamentals Revisited: Structure, Bonding, and Reactivity1.1 Organic Structure: A Brief History1.2 Proton Transfers Revisited: Acids and Bases1.3 Reactions and Reaction Mechanisms: "Electron Pushing"1.4 Resonance1.5 Spectroscopy and ChromatographyKey TermsAdditional Problems2. Stereochemistry2.1 Stereoisomers and Chirality2.2 Absolute Configuration2.3 Optical Purity and Configuration2.4 Conformation2.5 An Introduction to Asymmetric Synthesis: Asymmetric Induction2.6 How Well Did It Go? Measuring Enantiomer Ratios2.7 Chirality at Atoms Other Than Carbon: Inversion of Pyramidal CentersChapter SummaryKey TermsAdditional Problems3. Organic Short-hand: Acronyms and Name Reactions3.1 Organic Synthesis: A Brief Introduction3.2 Name Reactions: A Historical Overview3.3 Acronyms and Abbreviations4. Orbitals and Reactivity4.1 Introduction4.2 Atomic Orbitals: The History of the Modern Atomic Model4.3 Covalent Bonding and Molecular Orbitals4.4 Chemical Reactions: Frontier OrbitalsChapter SummaryKey TermsAdditional Problems5. Frontier Orbitals and Chemical Reactions5.1 Using Frontier Orbitals (FMOs) to Categorize Reactions and Reagents5.2 Categorizing Reactions Using FMP Pairings5.3 Stereoelectronic Effects5.4 Radical ReactionsChapter SummaryKey TermsAdditional Problems6. Synthetic Reactions I: Pericyclic Reactions and Conservation of Orbital Symmetry6.1 Introduction6.2 Molecular Orbitals of Conjugated Systems; Orbital Symmetry6.3 Qualitative Perturbation Theory: Approximating Frontier Orbitals of Substituted Alkenes and Dienes6.4 Sigmatropic Rearrangements6.5 Cycloaddition Reactions6.6 Ene, Retro-ene and Similar Reactions6.7 Combining Pericyclic Reactions in SequenceChapter SummaryKey TermsReaction SynopsesAdditional Problems7. Aromaticity7.1 Benzene: The Beginning7.2 Aromaticity and Antiaromaticity: The Huckel Molecular Orbital Model of Cyclic Polyenes7.3 How Does One Measure Aromaticity? Criteria for Aromaticity and its Quantification7.4 Mobius Aromaticity7.5 Homoaromaticity7.6 The Rest of the Story . . . The History and Mythology of BenzeneChapter SummaryKey TermsAdditional Problems8. Physical Organic Chemistry and Reaction Mechanisms8.1 Introduction8.2 Solvents and Solubility8.3 Reaction Kinetics8.4 Activation Parameters from Kinetic Studies8.5 Correlating Similar Reactions: Linear Free Energy Relationships8.6 Isotope and Element Effects8.7 Trapping and Crossover Experiments8.8 The Variable Transition State and the Concept of the Mechanistic Spectrum8.9 Using Regiochemistry and Stereochemistry8.10 The Reactivity-Selectivity PrincipleChapter SummaryKey TermsAdditional Problems9. Reactive Intermediates I: Carbocations9.1 Carbocations9.2 Rearrangements9.3 Neighboring Group Participation9.4 Non-classical Carbocations9.5 Methods for Generating CarbocationsChapter SummaryKey TermsReaction SynopsesAdditional Problems10. Synthetic Reactions II: Using Carbocations for C--C Bond Formation in Synthesis10.1 Introduction10.2 The Friedel-Crafts Reaction10.3 Formylation10.4 Addition of Stabilized Cations to Alkenes: The Prins, Mannich, and Mukaiyama ReactionsChapter SummaryKey TermsReaction SynopsesAdditional Problems11. Reactive Intermediates II: Carbanions and Their Reactivity11.1 Carbanions: Introduction and Overview11.2 Simple Organometallic Nucleophiles: Metal Alkyls11.3 Carbanions Stabilized by Heteroatoms11.4 Formation of Enolate Anions11.5 Rearrangements of CarbanionsChapter SummaryKey TermsReaction SynopsesAdditional Problems12. Synthetic Reactions III: Synthetic Reactions of Carbon Nucleophiles, Part 112.1 Carbon-Carbon Bond Formation: Carbon Nucleophiles and Electrophiles12.2 Substitution and Addition With Metal Alkyl Reagents Having C-M ? Bonds12.3 Metal Enolates: Versatile Carbon Nucleophiles12.4 The Aldol Addition Reaction12.5 Conjugate Addition of Enolates and Similar Compounds12.6 Azaenol Derivatives: Imines, Hydrazones and EnaminesChapter SummaryKey TermsReaction SynopsesAdditional Problems13. Reactive Intermediates III: Free Radicals, Carbenes, Arynes and Nitrenes13.1 Free Radicals13.2 Carbenes13.3 Nitrenes13.4 ArynesChapter SummaryKey TermsReaction SynopsesAdditional Problems14. Synthetic Reactions IV: Applications of Free Radical Chemistry in Synthesis14.1 Methods for Site-Specific Generation of Free Radicals14.2 Reactions of Free Radicals14.3 Reactions of Free Radicals Useful for Synthesis14.4 Additions and Cyclizations of Free Radicals14.5 Diradicals: Formation and Uses in SynthesisChapter SummaryKey TermsReaction SynopsesAdditional Problems15. Organic Synthesis I: Retrosynthetic Analysis, Protecting Groups, and the Strategy of Organic Synthesis15.1 What is Organic Synthesis?15.2 Organic Reactions: Tools of the Organic Chemist15.3 Retrosynthetic Analysis: An Introduction to the Vocabulary and Strategy of Organic Synthesis15.4 Applying RetrosyntheticAnalysis to a Real Example15.5 Selectivity Revisited15.6 Protection of Alcohols15.7 Protection of Aldehydes, Ketones, and Carboxylic Acids15.8 Protection of Amines15.9 Protecting Groups for HydrocarbonsChapter SummaryKey TermsReaction SynopsesAdditional Problems16. Synthetic Reactions V: Condensations and Cascade Reactions of Carbon Nucleophiles16.1 Addition, Condensation, Cascade Reactions: Definitions16.2 The Aldol Condensation and Related Reactions16.3 Condensations Where the Initial Adduct is Intercepted16.4 The Claisen Condensation and Related Reactions16.5 The Wittig, Horner-Wadsworth-Emmons, and Related Reactions16.6 Cascade Reactions Initiated by Carbon NucleophilesChapter SummaryKey TermsReaction SynopsesAdditional Problems17. Synthetic Reactions VI: Catalytic Reactions for C-C Bond Formation17.1 Catalysis and Green Chemistry17.2 Bonding in Organometallic Complexes17.3 Basic Organometallic Reactions: Reactions at the Metal17.4 Basic Organometallic Reactions: Reactions at the Ligand17.5 Hydrometalation: Making the Organometallic Reagents by Addition17.6 Palladium-Catalyzed Substitution: The Tsuji-Trost and Buchwald-Hartwig Reactions17.7 Cross-Coupling Reactions to Form C--C BondsChapter SummaryKey TermsReaction SynopsesAdditional Problems18. Redox Reactions I: Oxidation18.1 Introduction18.2 Overview of Oxidation18.3 Oxidation of Alcohols to Aldehydes and Ketones with Stoichiometric Metal-Based Reagents18.4 Oxidation of Alcohols Using Non-Metal-Based Reagents18.5 Oxidations to Carboxylic Acids18.6 Oxidation of Ethers and Amines18.7 Oxidative Rearrangements18.8 Oxidation of Unsaturated Hydrocarbons18.9 Oxidative Cleavage of Carbon-Carbon Bonds18.10 Oxidative Substitution of Carbon-Hydrogen ? Bonds18.11 Oxidation of Alkanes18.12 A Catalogue of Oxidation Reactions: Oxidation at a GlanceChapter SummaryKey TermsReaction SynopsesAdditional Problems19. Redox Reactions II: Reduction with Molecular Hydrogen or its Equivalent19.1 Overview of Reduction19.2 Catalytic Hydrogenation19.3 HydrogenlysisChapter SummaryKey TermsReaction SynopsesAdditional Problems20. Redox III: Reduction with Complex Metal Hydrides and Active Metals20.1 Reductions with Metal Hydrides20.2 Reduction by Hydrogen Transfer from Carbon20.3 Stereochemistry and Stereoselectivity in Hydride Reduction20.4 Reduction Using Metals20.5 Reduction of Carbonyl Compounds to Hydrocarbons20.6 A Catalogue of Reduction Reactions: Reduction at a GlanceChapter SummaryKey TermsReaction SynopsesAdditional Problems21. Aymmetric Oxidation and Reduction21.1 Asymmetric Redox Reactions: An Overview21.2 Sharpless Asymmetric Epoxidation of Allylic Alcohols21.3 Asymmetric Epoxidation of Unfunctionalized Alkenes21.4 Oxidation With Chiral Three-membered Heterocycles21.5 Asymmetric Dihydroxylation21.6 Kinetic Resolution of Alcohols21.7 Enantioselective Insertion into C--C and C--H Bonds21.8 Asymmetric Hydrogenation21.9 Asymmetric Reductions with Metal Hydrides and Metal Alkyls21.10 Enzymes: Biocatalysis of Redox ReactionsChapter SummaryKey TermsReaction SynopsesAdditional Problems22. Main-Group Organic Chemistry: Silicon, Phosphorus, Sulfur, Selenium and Tin22.1 Introduction22.2 Silanes and Stannanes as Directing Groups: Carbocation Chemistry22.3 Heteroatom-Centered Nucleophiles: Silyllithiums, Stannyllithiums , Sulfides and Selenides22.4 Reactions of Organophosphorus, Organosulfur and Organoselenium CompoundsChapter SummaryKey TermsReaction SynopsesAdditional Problems23. Modern Asymmetric Synthesis23.1 Controlling Absolute Stereochemistry23.2 Asymmetric Synthesis with Chiral Auxiliaries: Additions23.3 Asymmetric Substitution at Carbon: Alkylation of Enolates and Related Nucleophiles23.4 Catalytic Asymmetric Synthesis23.5 Representative Asymmetric SynthesesChapter SummaryKey TermsAdditional Problems

Editorial Reviews

"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 organicchemistry." --Scott Handy, Middle Tennessee State University