Chapter 1 Introduction

1.1 The Shape of Molecules

1.2 Atomic and Molecular Orbitals

1.3 Structure＆Bonding

1.4 Chemical Bonding and Valence

1.5 Covalent Bonding

1.6 Valence

1.7 Charge Distribution

1.8 Functional Groups

Chapter 2 Alkanes

2.1 Alkane Nomenclature

2.1.1 IUPAC Rules for Alkane Nomenclature

2.2 Conformational Stereoisomers

2.2.1 Ethane Conformations

2.2.2 Butane Conformations

2.3 Physical Properties of Alkanes

2.4 Chemical Properties of Alkanes

Chapter 3 Alkenes

3.1 Alkene and Cycloalkene Nomenclature

3.1.1 IUPAC Rules

3.1.2 Stereoisomers

3.1.3 Configurational Stereoisomers ofAlkenes

3.1.4 Nomenclature of Alkene Stereoisomers

3.1.5 The Sequence Rule forAssignment of Alkene Configurations

3.2 Physical Properties of Alkenes

3.3 Reactions of Alkenes

3.3.1 Addition Reactions of Alkenes

a．Addition of Strong Br？nsted Acids

b．Regioselectivity and the Markovnikov Rule

c．Rearrangement of Carbocations

d．Addition of Lewis Acids（Electrophilic Reagents）

e．Stereoselectivity in Addition Reactions to Double Bonds

f．Br？nsted Acid Additions

g．Addition Reactions Initiated by Electrophilic Halogen

h．Addition Reactions Involving Other Cyclic Onium Intermediates

3.3.2 Hydrogenation

3.3.3 Oxidations

（i）Hydroxylation

（ii）Epoxidation

（iii）Oxidative Cleavage of Double Bonds

3.3.4 Free Radical Reactions of Alkenes

a．Addition of Radicals to Alkenes

b．Allylic Substitution

Chapter 4 Alkynes

4.1 IUPAC Rules for Alkyne Nomenclature

4.2 Reactions of Alkynes

4.2.1 Adclition Reactions of Alkynes

a．Catalytic Hydrogenation

b．Addition by Electrophilic Reagents

c．Hydration of Alkynes and Tautomerism

d．Hydroboration Reactions

e．Oxidations

4.2.2 Nucleophilic Addition Reactions＆Reduction

4.2.3 Acidity of Terminal Alkynes

4.3 Physical Properties of Alkynes

Chapter 5 Dienes

5.1 Properties of Dienes

5.1.1 Addition Reactions of Dienes

5.1.2 Diels-Alder Cycloaddition

5.1.3 Stereospecificity

5.2 Properties of Cumulated Dienes

5.2.1 Addition Reactions of Allenes

Chapter 6 Cycloalkanes

6.1 IUPAC Rules for Cycloalkane Nomenclature

6.2 Ring Conformations

6.2.1 Substituted Cyclohexane Compounds

6.2.2 Conformational Structures of Disubstituted Cyclohexanes

6.2.3 Configurational Stereoisomers of Cycloalkanes

6.3 Cycloalkanes reactions

Chapter 7 Alkyl Halide

7.1 Naming

7.2 Alkyl Halide Reactions

7.3 Mechanisms of Nucleophilic Substitution Reactions

7.3.1 The SN2 Mechanism

7.3.2 The SN1 Mechanism

7.3.3 Activation by Electrophilic Cations

7.3.4 The E2 Reaction

7.3.5 Stereochemistry of the E2 Reaction

7.3.6 The E1 Reaction

7.3.7 Summary of Factors Influencing Alkyl Halide Reactions

7.4 Organometallic Compounds

7.4.1 Reactions of Alkyl Halides with Reducing Metals

7.5 Reactions of Dihalides

7.5.1 Preparation ofAlkynes by Dehydrohalogenation

Chapter 8 Aromatic compounds

8.1 Benzene Derivatives

8.2 Aromaticity

8.3 Aromatic Substitution Reactions

8.3.1 Substitution Reactions of Benzene and Other Aromatic Compounds

8.3.2 A Mechanism for Electrophilic Substitution Reactions of Benzene

8.3.3 Substitution Reactions of Benzene Derivatives

8.3.4 Characteristics of Specific Substitution Reactions

8.3.5 Electrophilic Substitution of Disubstituted Benzene Rings

8.4 Reactions of Substituent Groups

8.5 Reactions of Fused Benzene Rings

8.6 Nucleophilic Substitution,Elimination＆Addition Reactions of Benzene Derivatives

8.6.1 Substitution

8.6.2 Elimination

8.6.3 Addition

8.7 Fused Benzene Ring Compounds

8.8 Other Aromatic Systems

Chapter 9 Alcohol Phenol and Ethers

9.1 Alcohol

9.1.1 Alcohol Nomenclature

9.1.2 Alcohol Reactions

a．Electrophilic Substitution at Oxygen

b．Nucleophilic Substitution of the Hydroxyl Group

c．Elimination Reactions of Alcohols

d．Oxidation Reactions of Alcohols

9.2 Phenols

9.2.1 Phenols Nomenclature

9.2.2 Reactions of Phenols

a．Acidity of Phenols

b．Substitution of the Hydroxyl Hydrogen

c．Electrophilic Substitution of the Phenol Aromatic Ring

d．Oxidation of Phenols

9.3 Ethers

9.3.1 Ether Nomenclature

9.3.2 Preparation of Ethers

9.3.3 Reactions of Ethers

9.3.4 Reactions of Epoxides

9.4 Sulfur and Phosphorus Compounds

9.4.1 Nucleophilicity of Sulfur Compounds

9.4.2 Oxidation States of Sulfur Compounds

9.4.3 Oxidation of Alcohols by DMSO

9.4.4 Nucleophilicity of Phosphorus Compounds

9.4.5 Oxidation States of Phosphorus Compounds

9.4.6 Phosphorus Compounds as Reducing Agents

Chapter 10 Aldehydes and Ketones

10.1 Nomenclature of Aldehydes and Ketones

10.2 Synthetic Preparation of Aldehydes and Ketones

10.3 Properties of Aldehydes and Ketones

10.3.1 Reactions of Aldehydes and Ketones

a．Reversible Addition Reactions

b．Irreversible Addition Reactions

10.3.2 Other Carbonyl Group Reactions

a．Reduction

b．Oxidation

10.3.3 Reactions at the α-Carbon

a．Mechanism of Electrophilic α-Substitution

b．The Aldol Reaction

c．Dehydration of Aldol Products

d．Mixed A1dol Condensations

10.3.4 Irreversible Substitution Reactions

a．The Ambident Character of Enolate Anions

b．Alkylation Reactions of Enolate Anions

Chapter 11 Carboxylic Acids

11.1 Nomenclature of Carboxylic Acids

11.2 Carboxylic Acid Natural Products

11.3 Related Carbonyl Derivatives

11.4 Properties of Carboxylic Acids

11.4.1 Physical Properties ofCarboxylic Acids

11.4.2 Acidity of Carboxylic Acids

11.5 Preparation of Carboxylic Acids

11.6 Reactions of Carboxylic Acids

11.6.1 Salt Formation

11.6.2 Substitution of the Hydroxyl Hydrogen

11.6.3 Substitution of the Hydroxyl Group

11.7 Reductions＆Oxidations of Carboxylic Acids

11.7.1 Reduction

11.7.2 Oxidation

Chapter 12 Derivatives of Carboxylic Acids

12.1 Background and Properties

12.2 Nomenclature

12.3 Reactions ofCarboxylic Acid Derivatives

12.3.1 Acyl Group Substitution

12.3.2 Reduction

12.3.3 Reactions with Organometallic Reagents

12.3.4 Other Reactions

12.3.5 Reactions at the α-Carbon

a．Enolate Intermediates

b．Claisen Condensation

12.4 Condensation Reactions in Synthesis

a．Carbon-Carbon Bond Formation

b．Modification of Condensation Products

12.5 Fatty Acid Derivatives

12.5.1 Fatty Acids

12.5.2 Fats and Oils

12.5.3 Waxes

12.5.4 Terpenes

12.6 Biosynthetic Pathways

Chapter 13 Chemistry of Amines

13.1 Nomenclature and Structure ofAmines

13.2 A Structure Formula Relationship

13.3 Properties of Amines

13.3.1 Boiling Point and Water Solubility

13.3.2 Basicity of Amines

13.3.3 Acidity of Amines

13.3.4 Important Reagent Bases

13.4 Amine Reactions

13.4.1 Electrophilic Substitution at Nitrogen

13.4.2 Preparation of 1°-Amines

13.4.3 Preparation of 2°＆3°-Amines

13.4.4 Reaction of Amines with Nitrous Acid

13.4.5 Reactions of Aryl Diazonium Salts

13.4.6 Substitution and Elimination Reactions of Amines

13.4.7 Oxidation States of Nitrogen