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Preface to the Student

Preface to the Instructor

1 The Basics

1.1 Structure and Stability of Organic Compounds

1.1.1 Conventions of Drawing Structures；Grossman’S Rule

1.1.2 Lewis Structures；Resonance Structures

1.1.3 Molecular Shape；Hybridization

1.1.4 Aromaticity

1.2 BrCnsted Acidity and Basicity

1.2.1 PK Values

1.2.2 Tautomerism

1.3 Kinetics and Thermodynamics

1.4 Getting Started in Drawing a Mechanism

1.5 Classes of Overall Transformations

1.6 Classes of Mechanisms

1.6.1 Polar Mechanisms

1.6.2 Free.Radical Mechanisms

1.6.3 Pericyclic Mechanisms

1.6.4 Transition-Metal-Catalyzed and-Mediated Mechanisms

1.7 Summary

Problems

2 Polar Reactions under Basic Conditions

2.1 Substitution and Elimination at C(sp3)一X Bonds.Part I

2.1.1 Substitution by the SN2 Mechanism

2.1.2 Elimination by the E2 and Elcb Mechanisms

2.1.3 Predicting Substitution VS.Elimination

2.2 Addition of Nucleophiles to Electrophilic仃Bonds

2.2.1 Addition to Carbonyl Compounds

2.2.2 Conjugate Addition；The Michael Reaction

2.3 Substitution at C(sp2)一X Bouds

2.3.1 Substitution at Carbonyl C

2.3.2 Substitution at Alkenyl and Aryl C

2.3.3 Metal Insertion；Halogen-Metal Exchange

2.4 Substitution and Elimination at C(sp3)-X Bonds，Part II

2.4.1 Substitution by the SRNl Mechanism

2.4.2 Substitution by the Elimination-Addition Mechanism

2.4.3 Substitution by the One-Electron Transfer Mechanism

2.4.4 Metal Insertion；Halogen一Metal Exchange

2.4.5 Ol-Elimination；Generation and Reactions of Carbenes

2.5 Base-Promoted Rearrangements

2.5.1 Migration from C to C

2.5.2 Migration from C to O or N

2.5.3 Migration from B to C or O

2.6 Two Multistep Reactions

2.6.1 The Swem Oxidation

2.6.2 The Mitsunobu Reaction

2.7 Summary

Problems

3 Polar Reactions Under Acidic Conditions

3.1 Carbocations

3.1.1 CarbOCation Stability

3.1.2 Carbocation Generation；The Role of Protonation

3.1.3 Typical Reactions of Carbocations；Rearrangements

3.2 Substitution and 一Elimination Reactions at C(sp3)一X

3.2.1 Substitution by the SNl and SN2 Mechanisms

3.2.2 Elimination by the E1 Mechanism

3.2.3 Predicting Substitution VS.Elimination

3.3 Electrophilic Addition to Nucleophilic C=C Bonds

3.4 Substitution atNucleophilic C=C Bonds

3.4.1 Electrophilic Aromatic Substitution

3.4.2 Aromatic Substitution of Anilines via Diazonium Salts

3.4.3 Electrophilic Aliphatic Substitution

3.5 Nucleophilic Addition to and Substitution at Electrophilic Bonds

3.5.1 Heteroatom Nucleophiles

3.5.2 Carbon Nucleophiles

3.6 Summary

Problems

4 Pericyclic Reactions

4.1 Introduction

4.1.1 Classes of Pericyclic Reactions

4.1.2 Polyene MOs

……

5 Free.Radical Reactions

6 Transition-Metal-Mediated and-Cata！vzed Reactions

7 Mixed.Mechanism Probiems

A F.nal Word

Index