March's Advanced Organic Chemistry by Smith, Michael B. -- Read -- Imperial Library of Trantor

Index

Cover Title Page Copyright Preface Common Abbreviations Biographical Statement Part I: Introduction

Chapter 1: Localized Chemical Bonding

1.A. Covalent Bonding2 1.B. Multiple Valence 1.C. Hybridization 1.D. Multiple Bonds 1.E. Photoelectron Spectroscopy 1.F. Electronic Structures of Molecules 1.G. Electronegativity 1.H. Dipole Moment 1.I. Inductive and Field Effects 1.J. Bond Distances55 1.K. Bond Angles 1.L Bond Energies95

Chapter 2: Delocalized Chemical Bonding

2.A. Molecular Orbitals 2.B. Bond Energies and Distances in Compounds Containing Delocalized Bonds 2.C. Molecules that have Delocalized Bonds 2.D. Cross-Conjugation51 2.E. The Rules of Resonance 2.F. The Resonance Effect 2.G. Steric Inhibition of Resonance and the Influences of Strain 2.H. Pπ–dπ Bonding. Ylids 2.I. Aromaticity98 2.J. Alternant and Nonalternant Hydrocarbons208 2.K. Aromatic Systems with Electron Numbers Other than Six 2.L. Other Aromatic Compounds 2.M. Hyperconjugation 2.N. Tautomerism431

Chapter 3: Bonding Weaker Than Covalent

3.A. Hydrogen Bonding2 3.B. π–π Interactions 3.C. Addition Compounds 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.C. The Fischer Projection 4.D. Absolute Configuration 4.E. The Cause of Optical Activity 4.F. Molecules with more than One Stereogenic Center 4.G. Asymmetric Synthesis 4.H. Methods of Resolution160 4.I. Optical Purity207 4.J. cis–trans Isomerism 4.K. Out–In Isomerism 4.L. Enantiotopic and Diastereotopic Atoms, Groups, and Faces259 4.M. Stereospecific and Stereoselective Syntheses 4.N. Conformational Analysis 4.O. Molecular Mechanics412 4.P. Strain

Chapter 5: Carbocations, Carbanions, Free Radicals, Carbenes, and Nitrenes

5.A. Carbocations2 5.B. Carbanions 5.C. Free Radicals 5.D. Carbenes 5.E. Nitrenes

Chapter 6: Mechanisms and Methods of Determining Them

6.A. Types of Mechanism 6.B. Types of Reaction 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.G. The Hammond Postulate 6.H. Microscopic Reversibility 6.I. Marcus Theory 6.J. Methods of Determining Mechanisms33

Chapter 7: Irradiation Processes in Organic Chemistry

7.A. Photochemistry3 7.B. Sonochemistry 7.C. Microwave Chemistry

Chapter 8: Acids and Bases

8.A. Brønsted Theory 8.B. The Mechanism of Proton-Transfer Reactions 8.C. Measurements of Solvent Acidity124 8.D. Acid and Base Catalysis148 8.E. Lewis Acids and Bases 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.B. Steric Effects 9.C. Quantitative Treatments of the Effect of Structure on Reactivity16 9.D. Effect of Medium on Reactivity and Rate

Part II: Introduction

Chapter 10: Aliphatic Substitution, Nucleophilic and Organometallic

10.A. Mechanisms 10.B. SET Mechanisms 10.C. The Neighboring-Group Mechanism113 10.D. The SNI Mechanism 10.E. Nucleophilic Substitution at an Allylic Carbon: Allylic Rearrangements 10.F. Nucleophilic Substitution at an Aliphatic Trigonal Carbon: The Tetrahedral Mechanism 10.G. Reactivity 10.H. Reactions

Chapter 11: Aromatic Substitution, Electrophilic

11.A. Mechanisms 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 11.F. Reactions

12.A. Mechanisms 12.B. Reactivity 12.C. Reactions

Chapter 13: Aromatic Substitution: Nucleophilic and Organometallic

13.A. Mechanisms 13.B. Reactivity 13.C. Reactions

Chapter 14: Substitution Reactions: Radical

14.A. Mechanisms 14.B. Reactivity 14.C. Reactions

Chapter 15: Addition to Carbon–Carbon Multiple Bonds

15.A. Mechanisms 15.B. Orientation and Reactivity 15.C. Reactions

Chapter 16: Addition to Carbon–Hetero Multiple Bonds

16.A. Mechanism and Reactivity 16.B. Reactions

Chapter 17: Eliminations

17.A. Mechanisms And Orientation 17.B. Regiochemistry of the Double Bond 17.C. Stereochemistry of the Double Bond 17.D. Reactivity 17.E. Mechanisms and Orientation in Pyrolytic Eliminations 17.F. Reactions

Chapter 18: Rearrangements

18.A. Mechanisms 18.B. Longer Nucleophilic Rearrangements 18.C. Free Radical Rearrangements54 18.D. Carbene Rearrangements86 18.E. Electrophilic Rearrangements94 18.F. Reactions

Chapter 19: Oxidations and Reductions

19.A. Mechanisms 19.B. Reactions

Appendix A: The Literature of Organic Chemistry Appendix B: Classification of Reactions by Type of Compounds Synthesized Indexes

Author Index Subject Index