Advanced Organic Chemistry: Reactions and Mechanisms

About this book

*Ideal text for all undergraduate and graduate students who have previously taken a one-year course in Organic Chemistry, as well as serving students who have already had specialized courses in Physical Organic Chemistry, Stereochemistry, Spectroscopy, etc., and who need additional knowledge about Organic Reactions. Typically taught as a third semester undergraduate course or a senior/graduate course in organic reactions and mechanisms. *This text discusses important organic reactions and mechanisms not usually covered in depth in introductory organic chemistry courses. By stressing new material, it avoids student's hostility to repeating material previously studied, while still offering the opportunity to review important concepts and principles in novel settings.

Contents

1. Introduction. Mechanisms of Reactions. Electron Delocalization and Resonance. 2. Electrocyclic Reactions. Introduction. Conrotatory and Disrotatory Processes. Explanations for the Woodward-Hoffman Rules. Electrocyclic Reactions with Odd Numbers of Atoms. Photochemical Cyclizations. 3. Cycloaddiction and Cycloreversion Reactions. Introduction. Suprafacial and Antarafacial Addition. Selection Rules for Cycloaddition and Cycloreversion Reactions. Examples of Thermal Cycloaddition Reactions. Photochemical Cycloadditions. 4. Sigmatropic Reactions. Theory of Sigmatropic Shifts. Experimental Observations. Sigmatropic Rearrangements of Charged Systems. 5. Linear Free-Energy Relationships. The Hammett Equation. Separation of Polar, Resonance, and Steric Effects. 6. Migrations to Electron-Deficient Centers. Migrations to Electron-Deficient Carbons. The Nature of the Migrating Groups. Rearrangements of Carbocations. Long-Distance Migrations. Migrations to Nitrogen and Oxygen. 7. Neighboring-Group Effects and "Nonclassical" Cations. Substitution with Retention of Configuration. Cyclic Halonium Ions. Sulfur and Nitrogen Mustards. Trans/Cis Rate Ratios. Neighboring Acetoxy Groups. Cyclic Phenonium Ions. Double Bonds as Neighboring Groups. Cyclopropane Rings as Neighboring Groups. Neighboring Alkyl Groups: 2-Norbornyl Cations. 8. Rearrangements of Carbanions and Free Radicals. Carbanion Rearrangements. Rearrangements of Free Radicals. 9. Carbenes, Carbenoids, and Nitrenes. Introduction. Formation of Carbenes and Nitrenes. Singlet and Triplet Carbenes. Additions to Double Bonds. Insertion Reactions. Rearrangements. 10. Six-Membered Heterocyclic Rings. Aromatic Heterocyclic Molecules. Reactions of Pyridine and Its Analogs. Synthesis of Six-Membered Heterocyclic Rings. 11. Five-Membered Heterocyclic Rings. Introduction. Electron Delocalization and Aromaticity. Reactions of Five-Membered Heterocyclic Rings. Synthesis of Five-Membered Heteroaromatic Rings. Index.

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