reface to the Student
reface to the Instructor
1 The Basics
1.1 Structure and Stability of Organic Comounds
1.1.1 Conventions of Drawing Structures;Grossman’S Rule
1.1.2 Lewis Structures;Resonance Structures
1.1.3 Molecular Shae;Hybridization
1.1.4 Aromaticity
1.2 BrCnsted Acidity and Basicity
1.2.1 K 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 olar Mechanisms
1.6.2 Free.Radical Mechanisms
1.6.3 ericyclic Mechanisms
1.6.4 Transition-Metal-Catalyzed and-Mediated Mechanisms
1.7 Summary
roblems
2 olar Reactions under Basic Conditions
2.1 Substitution and Elimination at C(s3)一X Bonds.art I
2.1.1 Substitution by the SN2 Mechanism
2.1.2 Elimination by the E2 and Elcb Mechanisms
2.1.3 redicting Substitution VS.Elimination
2.2 Addition of Nucleohiles to Electrohilic仃Bonds
2.2.1 Addition to Carbonyl Comounds
2.2.2 Conjugate Addition;The Michael Reaction
2.3 Substitution at C(s2)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(s3)-X Bonds,art 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-romoted 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 Multiste Reactions
2.6.1 The Swem Oxidation
2.6.2 The Mitsunobu Reaction
2.7 Summary
roblems
3 olar Reactions Under Acidic Conditions
3.1 Carbocations
3.1.1 CarbOCation Stability
3.1.2 Carbocation Generation;The Role of rotonation
3.1.3 Tyical Reactions of Carbocations;Rearrangements
3.2 Substitution and 一Elimination Reactions at C(s3)一X
3.2.1 Substitution by the SNl and SN2 Mechanisms
3.2.2 Elimination by the E1 Mechanism
3.2.3 redicting Substitution VS.Elimination
3.3 Electrohilic Addition to Nucleohilic C=C Bonds
3.4 Substitution atNucleohilic C=C Bonds
3.4.1 Electrohilic Aromatic Substitution
3.4.2 Aromatic Substitution of Anilines via Diazonium Salts
3.4.3 Electrohilic Alihatic Substitution
3.5 Nucleohilic Addition to and Substitution at ElectrohilicBonds
3.5.1 Heteroatom Nucleohiles
3.5.2 Carbon Nucleohiles
3.6 Summary
roblems
4 ericyclic Reactions
4.1 Introduction
4.1.1 Classes of ericyclic Reactions
4.1.2 olyene MOs
……
5 Free.Radical Reactions
6 Transition-Metal-Mediated and-Cata!vzed Reactions
7 Mixed.Mechanism robiems
A F.nal Word
Index