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Chapter 1 Chemical Bonding1

1.1 Introduction1

1.2 Atoms,Electrons and Orbitals1

1.3 Ionic Bonds3

1.4 Covalent Bonds4

1.5 Double Bonds and Triple Bonds5

1.6 Polar Covalent Bonds and Electronegativity5

1.7 Formal Charge6

1.8 Structural Formulas of Organic Molecules6

1.9 Constitutional Isomers7

1.10 Resonance7

1.11 The Shapes of Some Simple Molecules8

1.12 Molecular Dipole Moments9

1.13 Electron Waves and Chemical Bonds10

1.14 Bonding in H2:The Valence Bond Model11

1.15 Bonding in H2:Molecular Orbital Method12

1.16 Orbital Hybridization and Bonding of Methane13

1.17 sp3 Hybridization and Bonding of Ethane14

1.18 sp2 Hybridization and Bonding of Ethylene14

1.19 sp Hybridization and Bonding of Acetylene15

1.20 Chapter Summary16

Review Questions18

References20

Chapter 2 Alkanes and Cycloalkanes21

2.1 Introduction21

2.2 Structure of Alkanes22

2.3 Nomenclature of Alkanes22

2.4 Alkyl Groups24

2.5 Conformational Isomerization of Alkanes24

2.6 Physical Properties of Alkanes27

2.7 Chemical Properties of Alkanes28

2.8 Cycloalkanes30

2.9 Chapter Summary35

Review Questions36

References38

Chapter 3 Alkenes and Alkynes39

3.1 Introduction of Alkenes39

3.2 Structure of Alkenes40

3.3 Nomenclature of Alkenes40

3.4 Physical Properties of Alkenes42

3.5 Chemical Properties of Alkenes42

3.6 Dienes50

3.7 Introduction of Alkynes54

3.8 Structure of Alkynes54

3.9 Nomenclature of Alkynes54

3.10 Physical Properties of Alkynes55

3.11 Chemical Properties of Alkynes55

3.12 Chapter Summary60

Review Questions61

References63

Chapter 4 Aromatic Compounds64

4.1 Introduction64

4.2 Benzene65

4.3 Nomenclature of Benzene Derivatives66

4.4 Physical Properties of Aromatic Hydrocarbon69

4.5 Chemistry of Benzene Derivatives70

4.6 Fused-Ring Aronatic Hydrocarbons80

4.7 Aromaticity and the Hückel Rule82

4.8 Chapter Summary84

Review Questions85

References88

Chapter 5 Stereochemistry89

5.1 Introduction89

5.2 Symmetry Elements90

5.3 Chiral Carbons91

5.4 Optical Activity94

5.5 Configuration of Enantiomers95

5.6 Isomers with More than One Asymmetric Centers96

5.7 Chapter Summary98

Review Questions98

References101

Chapter 6 Alkyl Halides102

6.1 Introduction102

6.2 Classification103

6.3 Nomenclature103

6.4 Reactions of Alkyl Halides104

6.5 Chapter Summary111

Review Questions112

References115

Chapter 7 Alcohols and Phenols116

7.1 Introduction116

7.2 Alcohols117

7.3 Phenols124

7.4 Chapter Summary127

Review Questions127

References129

Chapter 8 Ethers,Epoxides,Thiols and Sulfides130

8.1 Introduction130

8.2 Nomenclature of Ethers131

8.3 Structures and Physical Properties of Ethers132

8.4 Preparations of Ethers132

8.5 Reactions of Ethers134

8.6 Crown Ethers137

8.7 Epoxides138

8.8 Thiols and Sulfides142

8.9 Chapter Summary144

Review Questions147

References152

Chapter 9 Aldehydes and Ketones153

9.1 Introduction153

9.2 Classification and Nomenclature of Aldehydes and Ketones154

9.3 Structures of Aldehydes and Ketones155

9.4 Physical Properties of Aldehydes and Ketones156

9.5 Chemical Properties of Aldehydes and Ketones156

9.6 Quinones174

9.7 Chapter Summary177

Review Questions178

References183

Chapter 10 Carboxylic Acids and Substituted Carboxylic Acids184

10.1 Introduction184

10.2 Structure of Carboxylic Acids184

10.3 Classification of Carboxylic Acids185

10.4 Nomenclature of Carboxylic Acids185

10.5 Chemical Properties and Reactions of Carboxylic Acids186

10.6 Substituted Carboxylic Acids192

10.7 Chapter Summary194

Review Questions195

References198

Chapter 11 Carboxylic Acid Derivatives199

11.1 Introduction199

11.2 Acyl Halides200

11.3 Acid Anhydrides202

11.4 Esters203

11.5 Amides206

11.6 Urea207

11.7 The Claisen Condensation208

11.8 Chapter Summary209

Review Questions209

References212

Chapter 12 Amines213

12.1 Introduction213

12.2 Nomenclature of Amines214

12.3 Physical Properties of Amines215

12.4 Synthesis of Amines215

12.5 Reactions of Amines218

12.6 Reactions of Arenediazonium Salts221

12.7 Diazonium Coupling Reaction223

12.8 Chapter Summary223

Review Questions223

References226

Chapter 13 Aromatic Heterocycles227

13.1 Introduction227

13.2 Classification and Nomenclature of Heterocycles228

13.3 Five-Membered Heterocycles229

13.4 Chapter Summary240

Review Questions240

References242

Chapter 14 Carbohydrates243

14.1 Introduction243

14.2 Conformations of Sugars246

14.3 Polyfunctional Chemistry of Sugars251

14.4 Complex Sugars in Nature253

14.5 Chapter Summary256

Review Questions257

References258

Chapter 15 Lipids259

15.1 Introduction259

15.2 Triglycerides259

15.3 Phospholipids262

15.4 Steroids263

15.5 Chapter Summary264

Review Questions265

References268

Index269