Contents
Chapter 1: Localized Chemical Bonding
1.E. Photoelectron Spectroscopy
1.F. Electronic Structures of Molecules
1.I. Inductive and Field Effects
Chapter 2: Delocalized Chemical Bonding
2.B. Bond Energies and Distances in Compounds Containing Delocalized Bonds
2.C. Molecules that have Delocalized Bonds
2.G. Steric Inhibition of Resonance and the Influences of Strain
2.J. Alternant and Nonalternant Hydrocarbons208
2.K. Aromatic Systems with Electron Numbers Other than Six
Chapter 3: Bonding Weaker Than Covalent
3.D. Catenanes and Rotaxanes190
3.E. Cucurbit[n]uril-Based Gyroscane
Chapter 4: Stereochemistry and Conformation
4.A. Optical Activity and Chirality3
4.B. What Kinds of Molecules Display Optical Activity?
4.E. The Cause of Optical Activity
4.F. Molecules with more than One Stereogenic Center
4.L. Enantiotopic and Diastereotopic Atoms, Groups, and Faces259
4.M. Stereospecific and Stereoselective Syntheses
Chapter 5: Carbocations, Carbanions, Free Radicals, Carbenes, and Nitrenes
Chapter 6: Mechanisms and Methods of Determining Them
6.C. Thermodynamic Requirements For Reaction
6.D. Kinetic Requirements For Reaction
6.E. The Baldwin Rules For Ring Closure17
6.F. Kinetic and Thermodynamic Control
6.H. Microscopic Reversibility
6.J. Methods of Determining Mechanisms33
Chapter 7: Irradiation Processes in Organic Chemistry
8.B. The Mechanism of Proton-Transfer Reactions
8.C. Measurements of Solvent Acidity124
8.D. Acid and Base Catalysis148
8.F. The Effects of Structure on the Strengths of Acids and Bases175
8.G. The Effects of the Medium on Acid and Base Strength
Chapter 9: Effects of Structure and Medium on Reactivity
9.A. Resonance and Field Effects
9.C. Quantitative Treatments of the Effect of Structure on Reactivity16
9.D. Effect of Medium on Reactivity and Rate
Chapter 10: Aliphatic Substitution, Nucleophilic and Organometallic
10.C. The Neighboring-Group Mechanism113
10.E. Nucleophilic Substitution at an Allylic Carbon: Allylic Rearrangements
10.F. Nucleophilic Substitution at an Aliphatic Trigonal Carbon: The Tetrahedral Mechanism
Chapter 11: Aromatic Substitution, Electrophilic
11.B. Orientation and Reactivity
11.C. Quantitative Treatments of Reactivity in the Substrate
11.D. A Quantitative Treatment of Reactivity of the Electrophile: The Selectivity Relationship
11.E. The Effect of the Leaving Group
Chapter 12: Aliphatic, Alkenyl, and Alkynyl Substitution, Electrophilic and Organometallic
Chapter 13: Aromatic Substitution: Nucleophilic and Organometallic
Chapter 14: Substitution Reactions: Radical
Chapter 15: Addition to Carbon–Carbon Multiple Bonds
15.B. Orientation and Reactivity
Chapter 16: Addition to Carbon–Hetero Multiple Bonds
16.A. Mechanism and Reactivity
17.A. Mechanisms And Orientation
17.B. Regiochemistry of the Double Bond
17.C. Stereochemistry of the Double Bond
17.E. Mechanisms and Orientation in Pyrolytic Eliminations
18.B. Longer Nucleophilic Rearrangements
18.C. Free Radical Rearrangements54
18.D. Carbene Rearrangements86
18.E. Electrophilic Rearrangements94
Chapter 19: Oxidations and Reductions
Appendix A: The Literature of Organic Chemistry
Appendix B: Classification of Reactions by Type of Compounds Synthesized