1.1 The Goal of This book.

1.2 Mechanisms Are Your Keys to Success.

Chapter 2.  INTRO TO IONIC MECHANISMS.

2.1 Curved Arrows.

2.2 The Basic Moves.

2.3 Combining the Basic Moves.

Chapter 3.  ELECTROPHILIC AROMATIC SUBSTITUTION.

3.1 Halogenation and the role of Lewis Acids.

3.2 Nitration.

3.3 Friedel-Crafts Alkylation and Acylation.

3.4 Sulfonation.

3.5 Modifying the Nucleophilicity of the Nucleophile.

3.6 Predicting Directing Effects.

3.7 Identifying Activators and Deactivators.

3.8 Predicting and Exploiting Steric Effects.

3.9 Synthesis Strategies.

Chapter 4.  NUCLEOPHILIC AROMATIC SUBSTITUTION.

4.1 Criteria for Nucleophilic Aromatic Substitution.

4.2 SNAr Mechanism.

4.3 Elimination-Addition.

4.4 Mechanism Strategies.

Chapter 5.  KETONES AND ALDEHYDES.

5.1 Preparation of Ketones and Aldehydes.

5.2 Stability and Reactivity of the Carbonyl.

5.3 H-Nucleophiles.

5.4 O-Nucleophiles.

5.5 S-Nucleophiles.

5.6 N-Nucleophiles.

5.7 C-Nucleophiles.

5.8 Some Important Exceptions to the Rule.

5.9 How to Approach Synthesis Problems.

Chapter 6.  CARBOXYLIC ACID DERIVATIVES.

6.1 General Rules.

6.2 Acyl Halides.

6.3 Anhydrides.

6.4 Esters.

6.5 Amides and Nitriles.

6.6 Synthesis Problems.

Chapter 7.  ENOLS AND ENOLATES.

7.1 Keto-Enol Tautomerism.

7.2 Reactions Involving Enols.

7.3 Making Enolates.

7.4 Haloform Reactions.

7.5 Alkylation of Enolates.

7.6 Aldol Reaction and Aldol Condensation.

7.7 Claisen Condensation.

7.8 Decarboxylation Provides Some Useful Synthetic Techniques.

7.9 Michael Reactions.

Chapter 8.  AMINES.

8.1 Nucleophilicity and Basicity of Amines and Amides.

8.2 Preparation of Amines through SN2 Reactions.

8.3 Preparation of Amines through Reductive Amination.

8.4 Preparation of Amines from Amides.

8.5 Acylation of Amines.

8.6 Reactions of Amines with Nitrous Acid.

8.7 Aromatic Diazonium Salts.

Answer Key.

Index.