Writing Reaction Mechanisms in Organic Chemistry, Third Edition, is a guide to understanding the movements of atoms and electrons in the reactions of organic molecules. Expanding on the successful book by Miller and Solomon, this new edition further enhances your understanding of reaction mechanisms in organic chemistry and shows that writing mechanisms is a practical method of applying knowledge of previously encountered reactions and reaction conditions to new reactions.
The book has been extensively revised with new material including a completely new chapter on oxidation and reduction reactions including stereochemical reactions. It is also now illustrated with hundreds of colorful chemical structures to help you understand reaction processes more easily. The book also features new and extended problem sets and answers to help you understand the general principles and how to apply these to real applications. In addition, there are new information boxes throughout the text to provide useful background to reactions and the people behind the discovery of a reaction.
This new edition will be of interest to students and research chemists who want to learn how to organize what may seem an overwhelming quantity of information into a set of simple general principles and guidelines for determining and describing organic reaction mechanisms.
Key Features
- Extensively rewritten and reorganized with a completely new chapter on oxidation and reduction reactions including stereochemical reactions
- Essential for those who need to have mechanisms explained in greater detail than most organic chemistry textbooks provide
- Now illustrated with hundreds of colorful chemical structures to help you understand reaction processes more easily
- New and extended problem sets and answers to help you understand the general principles and how to apply this to real applications
- New information boxes throughout the text to provide useful background to reactions and the people behind the discovery of a reaction
- Acknowledgments for the Third 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
- Answers to Problems
- Chapter 2. General Principles for Writing Reaction Mechanisms
- 1. Balancing Equations
- 2. 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
- Answers to Problems
- 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
- Answers to Problems
- Chapter 4. Reactions Involving Acids and Other Electrophiles
- 1. 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
- Answers to Problems
- Chapter 5. Radicals and Radical Anions
- I. 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 Radicals
- 9. The SRN1 Reaction
- 10. The Birch Reduction
- 11. A Radical Mechanism for the Rearrangement of Some Anions
- Answers to Problems
- 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
- Answers to Problems
- Chapter 7. Oxidations and Reductions
- 1. Definition of Oxidation and Reduction
- 2. Oxidations
- 3. Reductions
- Answers to Problems
- Chapter 8. Additional Problems
- Answers to 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
- Kurti & Czako, Strategic Applications of Named Reactions in Organic Synthesis, 9780124297852, Mar. 2005, $114.00
- Smith, Organic Synthesis, 9781890661403, Jul. 2011, $130.00
- Grimshaw, Electrochemical Reactions and Mechanisms in Organic Chemistry, 9780444720078, $415.00, Dec. 2000
- van Eldik & Ivanovic-Burmacovic, Advances in Inorganic Chemistry Vol. 64: Inorganic/Bioinorganic Reaction Mechanisms, 9780123964625, Mar. 2012, $274.00
Upper-division undergraduate and graduate students in organic chemistry, synthetic organic chemistry, advanced organic chemistry, and organic chemistry reactions
