Writing Reaction Mechanisms in Organic Chemistry
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Table of contents
- Cover
- Writing Reaction Mechanisms in Organic Chemistryiii
- Copyright Pageiv
- Contentsv
- Preface to the Second Editionxi
- Preface to First Editionxiii
- Chapter 1. Introduction–Molecular Structure and Reactivity1
- 1. How to Write Lewis Structures and Calculate Formal Charges2
- 2. Representations of Organic Compounds12
- 3. Geometry and Hybridization14
- 4. Electronegativities and Dipoles16
- 5. Resonance Structures18
- 6. Aromaticity and Antiaromaticity26
- 7. Tautomers and Equilibrium29
- 8. Acidity and Basicity32
- 9. Nucleophiles and Electrophiles37
- Chapter 2. General Principles for Writing Reaction Mechanisms63
- 1. Balancing Equations64
- 2. Using Arrows to Show Moving Electrons66
- 3. Mechanisms in Acidic and Basic Media69
- 4. Electron-Rich Species: Bases or Nucleophiles?76
- 5. Trimolecular Steps78
- 6. Stability of Intermediates79
- 7. Driving Forces for Reactions82
- 8. Structural Relationships between Starting Materials and Products85
- 9. Solvent Effects86
- 10. A Last Word88
- Chapter 3. Reactions of Nucleophiles and Bases105
- 1. Nucleophilic Substitution106
- 2. Eliminations at Saturated Carbon120
- 3. Nucleophilic Addition to Carbonyl Compounds123
- 4. Base-Promoted Rearrangements141
- 5. Additional Mechanisms in Basic Media144
- Chapter 4. Reactions Involving Acids and Other Electrophiles195
- 1. Stability of Carbocations195
- 2. Formation of Carbocations196
- 3. The Fate of Carbocations199
- 4. Rearrangement of Carbocations200
- 5. Electrophilic Addition208
- 6. Acid-Catalyzed Reactions of Carbonyl Compounds213
- 7. Electrophilic Aromatic Substitution220
- 8. Carbenes224
- 9. Electrophilic Heteroatoms231
- Chapter 5. Radicals and Radical Anions283
- 1. Introduction283
- 2. Formation of Radicals284
- 3. Radical Chain Processes287
- 4. Radical Inhibitors290
- 5. Determining the Thermodynamic Feasibility of Radical Reactions292
- 6. Addition of Radicals294
- 7. Fragmentation Reactions299
- 8. Rearrangement of Radicals303
- 9. The Srnl Reaction307
- 10. The Birch Reduction310
- 11. A Radical Mechanism for the Rearrangement of Some Anions312
- Chapter 6. Pericyclic Reactions343
- 1. Introduction343
- 2. Electrocyclic Reactions346
- 3. Cycloadditions355
- 4. Sigmatropic Rearrangements366
- 5. The Ene Reaction373
- 6. A Molecular Orbital View of Pericyclic Processes379
- Chapter 7. Additional Problems417
- Appendix A: Lewis Structures of Common Functional Groups453
- Appendix B: Symbols and Abbreviations Used in Chemical Notation455
- Appendix C: Relative Acidities of Common Organic and Inorganic Substances457
- Index465
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 method of organizing and synthesizing an oftentimes overwhelming quantity of information into a set of general principles and guidelines for determining and describing organic reaction mechanisms.
NEW TO THIS EDITION
( Illustrated with hundreds of chemical structures, all redrawn from the first edition, with added
emphasis on three-dimensional structures and stereochemical aspects of reaction mechanisms
( Extensively rewritten and reorganized to make the presentation and format more accessible to first-year organic chemistry students, as well as advanced undergraduate and graduate students
( Chapter 6 is completely revised to streamline the treatment of pericyclic reactions, while introducing the principles underlying the symmetry operations and orbital correlation diagrams
( New appendixes in this edition contain easily referenced information on Lewis structures, chemical symbols and notation, and relative acidities of common functional groups
NEW TO THIS EDITION
( Illustrated with hundreds of chemical structures, all redrawn from the first edition, with added
emphasis on three-dimensional structures and stereochemical aspects of reaction mechanisms
( Extensively rewritten and reorganized to make the presentation and format more accessible to first-year organic chemistry students, as well as advanced undergraduate and graduate students
( Chapter 6 is completely revised to streamline the treatment of pericyclic reactions, while introducing the principles underlying the symmetry operations and orbital correlation diagrams
( New appendixes in this edition contain easily referenced information on Lewis structures, chemical symbols and notation, and relative acidities of common functional groups