Front Cover; Writing Reaction Mechanisms in Organic Chemistry; Copyright Page; Contents; Preface to the Second Edition; Preface to First Edition; Chapter 1. Introduction-Molecular Structure and Reactivity; 1. How to Write Lewis Structures and Calculate Formal Charges; 2. Representations of Organic Compounds; 3. Geometry and Hybridization; 4. Electronegativities and Dipoles; 5. Resonance Structures; 6. Aromaticity and Antiaromaticity; 7. Tautomers and Equilibrium; 8. Acidity and Basicity; 9. Nucleophiles and Electrophiles; Chapter 2. General Principles for Writing Reaction Mechanisms 1. Balancing Equations2. Using Arrows to Show Moving Electrons; 3. Mechanisms in Acidic and Basic Media; 4. Electron-Rich Species: Bases or Nucleophiles?; 5. Trimolecular Steps; 6. Stability of Intermediates; 7. Driving Forces for Reactions; 8. Structural Relationships between Starting Materials and Products; 9. Solvent Effects; 10. A Last Word; Chapter 3. Reactions of Nucleophiles and Bases; 1. Nucleophilic Substitution; 2. Eliminations at Saturated Carbon; 3. Nucleophilic Addition to Carbonyl Compounds; 4. Base-Promoted Rearrangements; 5. Additional Mechanisms in Basic Media Chapter 4. Reactions Involving Acids and Other Electrophiles1. Stability of Carbocations; 2. Formation of Carbocations; 3. The Fate of Carbocations; 4. Rearrangement of Carbocations; 5. Electrophilic Addition; 6. Acid-Catalyzed Reactions of Carbonyl Compounds; 7. Electrophilic Aromatic Substitution; 8. Carbenes; 9. Electrophilic Heteroatoms; Chapter 5. Radicals and Radical Anions; 1. Introduction; 2. Formation of Radicals; 3. Radical Chain Processes; 4. Radical Inhibitors; 5. Determining the Thermodynamic Feasibility of Radical Reactions; 6. Addition of Radicals; 7. Fragmentation Reactions 8. Rearrangement of Radicals9. The Srnl Reaction; 10. The Birch Reduction; 11. A Radical Mechanism for the Rearrangement of Some Anions; Chapter 6. Pericyclic Reactions; 1. Introduction; 2. Electrocyclic Reactions; 3. Cycloadditions; 4. Sigmatropic Rearrangements; 5. The Ene Reaction; 6. A Molecular Orbital View of Pericyclic Processes; Chapter 7. Additional Problems; Appendix A: Lewis Structures of Common Functional Groups; Appendix B: Symbols and Abbreviations Used in Chemical Notation; Appendix C: Relative Acidities of Common Organic and Inorganic Substances; Index

Writing Reaction Mechanisms in Organic Chemistry, Second Edition, is an invaluable guide to charting the movements of atoms and electrons in the reactions of organic molecules. Miller and Solomon illustrate that understanding organic reactions is based on applying general principles rather than the rote memorization of unrelated processes, and, in turn, emphasize that writing mechanisms is a practical method of applying knowledge of previously encountered reactions and reaction conditions to new reactions. Students and research chemists alike will find this book useful in providing a me