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Chapter 1 Introduction1

1.1 The Shape of Molecules2

1.2 Atomic and Molecular Orbitals5

1.3 Structure＆Bonding10

1.4 Chemical Bonding and Valence13

1.5 Covalent Bonding14

1.6 Valence17

1.7 Charge Distribution17

1.8 Functional Groups21

Chapter 2 Alkanes25

2.1 Alkane Nomenclature25

2.1.1 IUPAC Rules for Alkane Nomenclature27

2.2 Conformational Stereoisomers28

2.2.1 Ethane Conformations29

2.2.2 Butane Conformations31

2.3 Physical Properties of Alkanes33

2.4 Chemical Properties of Alkanes36

Chapter 3 Alkenes40

3.1 Alkene and Cycloalkene Nomenclature40

3.1.1 IUPAC Rules40

3.1.2 Stereoisomers41

3.1.3 Configurational Stereoisomers ofAlkenes42

3.1.4 Nomenclature of Alkene Stereoisomers44

3.1.5 The Sequence Rule forAssignment of Alkene Configurations45

3.2 Physical Properties of Alkenes46

3.3 Reactions of Alkenes47

3.3.1 Addition Reactions of Alkenes47

a．Addition of Strong Br？nsted Acids47

b．Regioselectivity and the Markovnikov Rule49

c．Rearrangement of Carbocations54

d．Addition of Lewis Acids（Electrophilic Reagents）55

e．Stereoselectivity in Addition Reactions to Double Bonds60

f．Br？nsted Acid Additions61

g．Addition Reactions Initiated by Electrophilic Halogen61

h．Addition Reactions Involving Other Cyclic Onium Intermediates63

3.3.2 Hydrogenation66

3.3.3 Oxidations68

（i）Hydroxylation68

（ii）Epoxidation69

（iii）Oxidative Cleavage of Double Bonds71

3.3.4 Free Radical Reactions of Alkenes74

a．Addition of Radicals to Alkenes74

b．Allylic Substitution75

Chapter 4 Alkynes79

4.1 IUPAC Rules for Alkyne Nomenclature79

4.2 Reactions of Alkynes80

4.2.1 Adclition Reactions of Alkynes80

a．Catalytic Hydrogenation80

b．Addition by Electrophilic Reagents82

c．Hydration of Alkynes and Tautomerism86

d．Hydroboration Reactions88

e．Oxidations89

4.2.2 Nucleophilic Addition Reactions＆Reduction90

4.2.3 Acidity of Terminal Alkynes91

4.3 Physical Properties of Alkynes93

Chapter 5 Dienes96

5.1 Properties of Dienes96

5.1.1 Addition Reactions of Dienes98

5.1.2 Diels-Alder Cycloaddition101

5.1.3 Stereospecificity103

5.2 Properties of Cumulated Dienes107

5.2.1 Addition Reactions of Allenes109

Chapter 6 Cycloalkanes115

6.1 IUPAC Rules for Cycloalkane Nomenclature116

6.2 Ring Conformations118

6.2.1 Substituted Cyclohexane Compounds122

6.2.2 Conformational Structures of Disubstituted Cyclohexanes123

6.2.3 Configurational Stereoisomers of Cycloalkanes125

6.3 Cycloalkanes reactions126

Chapter 7 Alkyl Halide130

7.1 Naming130

7.2 Alkyl Halide Reactions131

7.3 Mechanisms of Nucleophilic Substitution Reactions143

7.3.1 The SN2 Mechanism143

7.3.2 The SN1 Mechanism144

7.3.3 Activation by Electrophilic Cations147

7.3.4 The E2 Reaction148

7.3.5 Stereochemistry of the E2 Reaction154

7.3.6 The E1 Reaction157

7.3.7 Summary of Factors Influencing Alkyl Halide Reactions159

7.4 Organometallic Compounds161

7.4.1 Reactions of Alkyl Halides with Reducing Metals161

7.5 Reactions of Dihalides164

7.5.1 Preparation ofAlkynes by Dehydrohalogenation167

Chapter 8 Aromatic compounds171

8.1 Benzene Derivatives171

8.2 Aromaticity174

8.3 Aromatic Substitution Reactions179

8.3.1 Substitution Reactions of Benzene and Other Aromatic Compounds179

8.3.2 A Mechanism for Electrophilic Substitution Reactions of Benzene181

8.3.3 Substitution Reactions of Benzene Derivatives183

8.3.4 Characteristics of Specific Substitution Reactions191

8.3.5 Electrophilic Substitution of Disubstituted Benzene Rings195

8.4 Reactions of Substituent Groups198

8.5 Reactions of Fused Benzene Rings204

8.6 Nucleophilic Substitution,Elimination＆Addition Reactions of Benzene Derivatives206

8.6.1 Substitution206

8.6.2 Elimination207

8.6.3 Addition209

8.7 Fused Benzene Ring Compounds210

8.8 Other Aromatic Systems213

Chapter 9 Alcohol Phenol and Ethers220

9.1 Alcohol220

9.1.1 Alcohol Nomenclature220

9.1.2 Alcohol Reactions222

a．Electrophilic Substitution at Oxygen223

b．Nucleophilic Substitution of the Hydroxyl Group226

c．Elimination Reactions of Alcohols232

d．Oxidation Reactions of Alcohols235

9.2 Phenols239

9.2.1 Phenols Nomenclature239

9.2.2 Reactions of Phenols240

a．Acidity of Phenols241

b．Substitution of the Hydroxyl Hydrogen243

c．Electrophilic Substitution of the Phenol Aromatic Ring243

d．Oxidation of Phenols244

9.3 Ethers246

9.3.1 Ether Nomenclature246

9.3.2 Preparation of Ethers247

9.3.3 Reactions of Ethers249

9.3.4 Reactions of Epoxides251

9.4 Sulfur and Phosphorus Compounds252

9.4.1 Nucleophilicity of Sulfur Compounds252

9.4.2 Oxidation States of Sulfur Compounds253

9.4.3 Oxidation of Alcohols by DMSO255

9.4.4 Nucleophilicity of Phosphorus Compounds257

9.4.5 Oxidation States of Phosphorus Compounds258

9.4.6 Phosphorus Compounds as Reducing Agents259

Chapter 10 Aldehydes and Ketones265

10.1 Nomenclature of Aldehydes and Ketones265

10.2 Synthetic Preparation of Aldehydes and Ketones270

10.3 Properties of Aldehydes and Ketones272

10.3.1 Reactions of Aldehydes and Ketones274

a．Reversible Addition Reactions274

b．Irreversible Addition Reactions281

10.3.2 Other Carbonyl Group Reactions288

a．Reduction288

b．Oxidation291

10.3.3 Reactions at the α-Carbon292

a．Mechanism of Electrophilic α-Substitution293

b．The Aldol Reaction296

c．Dehydration of Aldol Products297

d．Mixed A1dol Condensations300

10.3.4 Irreversible Substitution Reactions302

a．The Ambident Character of Enolate Anions302

b．Alkylation Reactions of Enolate Anions305

Chapter 11 Carboxylic Acids312

11.1 Nomenclature of Carboxylic Acids312

11.2 Carboxylic Acid Natural Products314

11.3 Related Carbonyl Derivatives316

11.4 Properties of Carboxylic Acids318

11.4.1 Physical Properties ofCarboxylic Acids318

11.4.2 Acidity of Carboxylic Acids320

11.5 Preparation of Carboxylic Acids324

11.6 Reactions of Carboxylic Acids326

11.6.1 Salt Formation326

11.6.2 Substitution of the Hydroxyl Hydrogen326

11.6.3 Substitution of the Hydroxyl Group328

11.7 Reductions＆Oxidations of Carboxylic Acids331

11.7.1 Reduction331

11.7.2 Oxidation332

Chapter 12 Derivatives of Carboxylic Acids336

12.1 Background and Properties336

12.2 Nomenclature337

12.3 Reactions ofCarboxylic Acid Derivatives339

12.3.1 Acyl Group Substitution339

12.3.2 Reduction345

12.3.3 Reactions with Organometallic Reagents354

12.3.4 Other Reactions356

12.3.5 Reactions at the α-Carbon357

a．Enolate Intermediates359

b．Claisen Condensation361

12.4 Condensation Reactions in Synthesis365

a．Carbon-Carbon Bond Formation366

b．Modification of Condensation Products367

12.5 Fatty Acid Derivatives372

12.5.1 Fatty Acids372

12.5.2 Fats and Oils374

12.5.3 Waxes377

12.5.4 Terpenes377

12.6 Biosynthetic Pathways380

Chapter 13 Chemistry of Amines389

13.1 Nomenclature and Structure ofAmines389

13.2 A Structure Formula Relationship393

13.3 Properties of Amines394

13.3.1 Boiling Point and Water Solubility394

13.3.2 Basicity of Amines395

13.3.3 Acidity of Amines398

13.3.4 Important Reagent Bases399

13.4 Amine Reactions400

13.4.1 Electrophilic Substitution at Nitrogen400

13.4.2 Preparation of 1°-Amines403

13.4.3 Preparation of 2°＆3°-Amines407

13.4.4 Reaction of Amines with Nitrous Acid409

13.4.5 Reactions of Aryl Diazonium Salts413

13.4.6 Substitution and Elimination Reactions of Amines417

13.4.7 Oxidation States of Nitrogen423