有机化学 第6版 改编版2025|PDF|Epub|mobi|kindle电子书版本百度云盘下载

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Chapter 1 Introduction and Review1

1-1 The Origins of Organic Chemistry1

1-2 Principles of Atomic Structure2

1-3 Bond Formation:The Octet Rule5

1-4 Lewis Structures6

1-5 Multiple Bonding7

1-6 Electronegativity and Bond Polarity8

1-7 Formal Charges9

1-8 Ionic Structures11

1-9 Resonance12

1-10 Structural Formulas15

1-11 Molecular Formulas and Empirical Formulas18

1-12 Arrhenius Acids and Bases19

1-13 Br？nsted-Lowry Acids and Bases21

1-14 Lewis Acids and Bases26

Summary in Chinese28

Study Problems30

Chapter 2 Structure and Properties of Organic Molecules34

2-1 Wave Properties of Electrons in Orbitals34

2-2 Molecular Orbitals36

2-3 Pi Bonding39

2-4 Hybridization and Molecular Shapes41

2-5 Drawing Three-Dimensional Molecules44

2-6 General Rules of Hybridization and Geometry45

2-7 Bond Rotation48

2-8 Isomerism50

2-9 Polarity of Bonds and Molecules53

2-10 Intermolecular Forces56

2-11 Polarity Effects on Solubilities59

Summary in Chinese61

Study Problems63

Chapter 3 Brief Introduction and Nomenclature of Organic Compounds66

3-1 Hydrocarbons66

3-2 Organic Compounds Containing Oxygen69

3-3 Organic Compounds Containing Nitrogen71

3-4 Nomenclature of Alkanes72

3-5 Nomenclature of Alkenes79

3-6 Nomenclature of Alkynes84

3-7 Nomenclature of Cycloalkanes85

3-8 Nomenclature of Benzene Derivatives88

3-9 Nomenclature of Alkyl Halides90

3-10 Nomenclature of Alcohols and Thiols92

3-11 Nomenclature of Ethers and Sulfides95

3-12 Nomenclature of Amines98

3-13 Nomenclature of Ketones and Aldehydes101

3-14 Nomenclature of Carboxylic Acids103

3-15 Structure and Nomenclature of Acid Derivatives107

Summary in Chinese113

Study Problems116

Chapter 4 Structure and Stereochemistry of Alkanes120

4-1 Physical Properties of Alkanes120

4-2 Uses and Sources of Alkanes122

4-3 Reactions of Alkanes125

4-4 Structure and Conformations of Alkanes126

4-5 Cycloalkanes131

4-6 Cyclohexane Conformations135

4-7 Conformations of Monosubstituted Cyclohexanes138

4-8 Conformations of Disubstituted Cyclohexanes141

Summary in Chinese144

Study Problems146

Chapter 5 The Study of Chemical Reactions148

5-1 Introduction148

5-2 Chlorination of Methane148

5-3 The Free-Radical Chain Reaction149

5-4 Equilibrium Constants and Free Energy152

5-5 Enthalpy and Entropy154

5-6 Bond-Dissociation Enthalpies156

5-7 Enthalpy Changes in Chlorination158

5-8 Kinetics and the Rate Equation159

5-9 Activation Energy and the Temperature Dependence of Rates160

5-10 Transition States162

5-11 Rates of Multistep Reactions163

5-12 Temperature Dependence of Halogenation164

5-13 Selectivity in Halogenation165

5-14 The Hammond Postulate170

5-15 Radical Inhibitors172

5-16 Reactive Intermediates173

Summary in Chinese179

Study Problems181

Chapter 6 Stereochemistry184

6-1 Introduction184

6-2 Chirality185

6-3 (R)and(S)Nomenclature of Asymmetric Carbon Atoms190

6-4 Optical Activity193

6-5 Racemic Mixtures196

6-6 Enantiomeric Excess and Optical Purity197

6-7 Chirality of Conformationally Mobile Systems198

6-8 Chiral Compounds without Asymmetric Atoms200

6-9 Fischer Projections202

6-10 Diastereomers206

6-11 Stereochemistry of Molecules with Two or More Asymmetric Carbons208

6-12 Meso Compounds209

6-13 Absolute and Relative Configuration211

6-14 Physical Properties of Diastereomers212

6-15 Resolution of Enantiomers214

Summary in Chinese216

Study Problems218

Chapter 7 Alkyl Halides:Nucleophilic Substitution and Elimination221

7-1 Introduction221

7-2 Common Uses of Alkyl Halides222

7-3 Structure of Alkyl Halides224

7-4 Physical Properties of Alkyl Halides225

7-5 Preparation of Alkyl Halides226

7-6 Reactions of Alkyl Halides:Substitution and Elimination230

7-7 Second-Order Nucleophilic Substitution:The SN2 Reaction231

7-8 Generality of the SN2 Reaction233

7-9 Factors Affecting SN2 Reactions:Strength of the Nucleophile234

7-10 Reactivity of the Substrate in SN2 Reactions239

7-11 Stereochemistry of the SN2 Reaction242

7-12 First-Order Nucleophilic Substitution:The SN1 Reaction244

7-13 Stereochemistry of the SN1 Reaction248

7-14 Rearrangements in SN1 Reactions250

7-15 Comparison of SN1 and SN2 Reactions253

7-16 First-Order Elimination:The E1 Reaction254

7-17 Positional Orientation of Elimination:Zaitsev's Rule259

7-18 Second-Order Elimination:The E2 Reaction261

7-19 Stereochemistry of the E2 Reaction263

7-20 Comparison of E1 and E2 Elimination Mechanisms265

Summary in Chinese267

Study Problems272

Chapter 8 Structure and Synthesis of Alkenes276

8-1 Introduction276

8-2 The Orbital Description of the Alkene Double Bond277

8-3 Elements of Unsaturation278

8-4 Commercial Importance of Alkenes281

8-5 Stability of Alkenes282

8-6 Physical Properties of Alkenes287

8-7 Alkene Synthesis by Elimination of Alkyl Halides289

8-8 Alkene Synthesis by Dehydration of Alcohols296

8-9 Alkene Synthesis by High-Temperature Industrial Methods297

Summary in Chinese299

Study Problems301

Chapter 9 Reactions of Alkenes304

9-1 Reactivity of the Carbon-Carbon Double Bond304

9-2 Electrophilic Addition to Alkenes305

9-3 Addition of Hydrogen Halides to Alkenes306

9-4 Addition of Water:Hydration of Alkenes311

9-5 Hydration by Oxymercuration-Demercuration313

9-6 Alkoxymercuration-Demercuration315

9-7 Hydroboration of Alkenes316

9-8 Addition of Halogens to Alkenes321

9-9 Formation of Halohydrins324

9-10 Catalytic Hydrogenation of Alkenes326

9-11 Addition of Carbenes to Alkenes329

9-12 Epoxidation of Alkenes331

9-13 Acid-Catalyzed Opening of Epoxides332

9-14 Syn Hydroxylation of Alkenes334

9-15 Oxidative Cleavage of Alkenes336

9-16 Polymerization of Alkenes339

Summary in Chinese342

Study Problems345

Chapter 10 Alkynes349

10-1 Introduction349

10-2 Physical Properties of Alkynes350

10-3 Commercial Importance of Alkynes350

10-4 Electronic Structure of Alkynes352

10-5 Acidity of Alkynes;Formation of Acetylide Ions353

10-6 Synthesis of Alkynes from Acetylides355

10-7 Synthesis of Alkynes by Elimination Reactions358

10-8 Addition Reactions of Alkynes360

10-9 Oxidation of Alkynes369

Summary in Chinese371

Study Problems374

Chapter 11 Conjugated Systems and Orbital Symmetry377

11-1 Introduction377

11-2 Stabilities of Dienes377

11-3 Molecular Orbitals of a Conjugated System379

11-4 Allylic Cations383

11-5 1,2-and 1,4-Addition to Conjugated Dienes384

11-6 Kinetic versus Thermodynamic Control in the Addition of HBr to 1,3-Butadiene385

11-7 Allylic Radicals388

11-8 Molecular Orbitals of the Allylic System390

11-9 Electronic Configurations of the Allyl Radical,Cation,and Anion391

11-10 SN2 Displacement Reactions of Allylic Halides and Tosylates392

11-11 The Diels-Alder Reaction393

11-12 The Diels-Alder as an Example of a Pericyclic Reaction400

Summary in Chinese404

Study Problems406

Chapter 12 Infrared and Ultraviolet Spectros-copy409

12-1 Introduction409

12-2 The Electromagnetic Spectrum410

12-3 The Infrared Region411

12-4 Molecular Vibrations412

12-5 IR-Active and IR-Inactive Vibrations413

12-6 Measurement of the IR Spectrum414

12-7 Infrared Spectroscopy of Hydrocarbons416

12-8 Characteristic Absorptions of Alcohols and Amines417

12-9 Characteristic Absorptions of Carbonyl Compounds417

12-10 Characteristic Absorptions of C—N Bonds418

12-11 Simplified Summary of IR Stretching Frequencies419

12-12 Reading and Interpreting IR Spectra420

12-13 Ultraviolet Absorption Spectroscopy422

12-14 Ultraviolet Light and Electronic Transitions423

12-15 Measurement of the UV-Visible Spectrum424

12-16 Interpreting UV-Visible Spectra426

Summary in Chinese429

Study Problems431

Chapter 13 Nuclear Magnetic Resonance Spectroscopy and Mass Spectrometry434

13-1 Introduction to Nuclear Magnetic Resonance Spectroscopy434

13-2 Theory of Nuclear Magnetic Resonance434

13-3 Magnetic Shielding by Electrons436

13-4 The NMR Spectrometer437

13-5 The Chemical Shift437

13-6 The Number of Signals441

13-7 Areas of the Peaks442

13-8 Spin-Spin Splitting443

13-9 Carbon-13 NMR Spectroscopy448

13-10 Interpreting Carbon NMR Spectra451

13-11 Introduction to Mass Spectrometry452

13-12 Determination of the Molecular Formula by Mass Spectrometry454

13-13 Fragmentation Patterns in Mass Spectrometry456

Summary in Chinese460

Study Problems462

Chapter 14 Structure and Synthesis of Alcohols466

14-1 Introduction466

14-2 Structure and Classification of Alcohols466

14-3 Physical Properties of Alcohols467

14-4 Commercially Important Alcohols470

14-5 Acidity of Alcohols and Phenols471

14-6 Organometallic Reagents for Alcohol Synthesis475

14-7 Synthesis of Alcohols:Addition of Organometallic Reagents to Carbonyl Compounds477

14-8 Side Reactions of Organometallic Reagents:Reduction of Alkyl Halides484

14-9 Synthesis of 1°and 2°Alcohols:Reduction of the Carbonyl Group486

14-10 Thiols(Mercaptans)489

Summary in Chinese491

Study Problems494

Chapter 15 Reactions of Alcohols498

15-1 Oxidation States of Alcohols and Related Functional Groups498

15-2 Oxidation of Alcohols499

15-3 Additional Methods for Oxidizing Alcohols501

15-4 Alcohols as Nucleophiles and Electrophiles;Formation of Tosylates503

15-5 Reduction of Alcohols506

15-6 Reactions of Alcohols with Hydrohalic Acids507

15-7 Reactions of Alcohols with Phosphorus Halides511

15-8 Reactions of Alcohols with Thionyl Chloride512

15-9 Dehydration Reactions of Alcohols514

15-10 Unique Reactions of Diols517

15-11 Esterification of Alcohols520

15-12 Reactions of Alkoxides520

Summary in Chinese522

Study Problems525

Chapter 16 Ethers,Epoxides,and Sulfides529

16-1 Introduction529

16-2 Physical Properties of Ethers529

16-3 Spectroscopy of Ethers534

16-4 Synthesis of Ethers534

16-5 Cleavage of Ethers by HBr and HI536

16-6 Autoxidation of Ethers538

16-7 Synthesis of Epoxides539

16-8 Acid-Catalyzed Ring Opening of Epoxides541

16-9 Base-Catalyzed Ring Opening of Epoxides543

16-10 Orientation of Epoxide Ring Opening544

16-11 Reactions of Epoxides with Grignard and Organolithium Reagents546

16-12 Epoxy Resins:The Advent of Modern Glues547

16-13 Sulfides(Thioethers)548

Summary in Chinese550

Study Problems553

Chapter 17 Aromatic Compounds556

17-1 Introduction:The Discovery of Benzene556

17-2 The Structure and Properties of Benzene556

17-3 The Molecular Orbitals of Benzene560

17-4 Aromatic,Antiaromatic,and Nonaromatic Compounds562

17-5 Hückel's Rule563

17-6 Molecular Orbital Derivation of Hückel's Rule565

17-7 Aromatic Ions566

17-8 Heterocyclic Aromatic Compounds570

17-9 Polynuclear Aromatic Hydrocarbons573

17-10 Aromatic Allotropes of Carbon574

17-11 Fused Heterocyclic Compounds576

17-12 Physical Properties of Benzene and Its Derivatives576

17-13 Spectroscopy of Aromatic Compounds578

Summary in Chinese578

Study Problems579

Chapter 18 Reactions of Aromatic Compounds584

18-1 Electrophilic Aromatic Substitution584

18-2 Halogenation of Benzene585

18-3 Nitration of Benzene587

18-4 Sulfonation of Benzene588

18-5 Nitration of Toluene:The Effect of Alkyl Substitution591

18-6 Activating,Ortho,Para-Directing Substituents593

18-7 Deactivating,Meta-Directing Substituents595

18-8 Halogen Substituents:Deactivating,but Ortho,Para-Directing598

18-9 Effects of Multiple Substituents on Electrophilic Aromatic Substitution600

18-10 The Friedel-Crafts Alkylation602

18-11 The Friedel-Crafts Acylation605

18-12 Nucleophilic Aromatic Substitution609

18-13 Addition Reactions of Benzene Derivatives613

18-14 Side-Chain Reactions of Benzene Derivatives615

18-15 Reactions of Phenols618

Summary in Chinese621

Study Problems624

Chapter 19 Ketones and Aldehydes629

19-1 Carbonyl Compounds629

19-2 Structure of the Carbonyl Group630

19-3 Physical Properties of Ketones and Aldehydes630

19-4 Spectroscopy of Ketones and Aldehydes633

19-5 Industrial Importance of Ketones and Aldehydes633

19-6 Syntheses of Ketones and Aldehydes634

19-7 Reactions of Ketones and Aldehydes:Nucleophilic Addition639

19-8 Hydration of Ketones and Aldehydes642

19-9 Formation of Acetals644

19-10 Formation of Cyanohydrins648

19-11 Formation of Imines650

19-12 Condensations with Hydroxylamine and Hydrazines653

19-13 The Wittig Reaction654

19-14 Oxidation of Aldehydes657

19-15 Reductions of Ketones and Aldehydes658

Summary in Chinese660

Study Problems664

Chapter 20 Amines668

20-1 Introduction668

20-2 Structure of Amines669

20-3 Physical Properties of Amines670

20-4 Basicity of Amines672

20-5 Effects on Amine Basicity674

20-6 Salts of Amines677

20-7 Amine Salts as Phase-Transfer Catalysts678

20-8 Spectroscopy of Amines679

20-9 Aromatic Substitution of Arylamines and Pyridine680

20-10 Alkylation of Amines by Alkyl Halides683

20-11 Acylation of Amines by Acid Chlorides684

20-12 Formation of Sulfonamides685

20-13 Amines as Leaving Groups:The Hofmann Elimination686

20-14 Oxidation of Amines;The Cope Elimination689

20-15 Reactions of Amines with Nitrous Acid690

20-16 Reactions of Arenediazonium Salts691

20-17 Synthesis of Amines by Reductive Amination695

20-18 Synthesis of Amines by Acylation-Reduction697

20-19 Syntheses Limited to Primary Amines698

Summary in Chinese703

Study Problems707

Chapter 21 Carboxylic Acids712

21-1 Introduction712

21-2 Structure and Physical Properties of Carboxylic Acids712

21-3 Acidity of Carboxylic Acids715

21-4 Salts of Carboxylic Acids718

21-5 Commercial Sources of Carboxylic Acids720

21-6 Spectroscopy of Carboxylic Acids721

21-7 Synthesis of Carboxylic Acids722

21-8 Condensation of Acids with Alcohols:The Fischer Esterification723

21-9 Esterification Using Diazomethane726

21-10 Condensation of Acids with Amines:Direct Synthesis of Amides726

21-11 Formation of Acid Chlorides727

21-12 Reduction of Carboxylic Acids727

21-13 Alkylation of Carboxylic Acids to Form Ketones728

Summary in Chinese729

Study Problems731

Chapter 22 Carboxylic Acid Derivatives736

22-1 Introduction736

22-2 Physical Properties of Carboxylic Acid Derivatives737

22-3 Spectroscopy of Carboxylic Acid Derivatives739

22-4 Interconversion of Acid Derivatives by Nucleophilic Acyl Substitution741

22-5 Transesterification748

22-6 Hydrolysis of Carboxylic Acid Derivatives750

22-7 Reduction of Acid Derivatives753

22-8 Reactions of Acid Derivatives with Organometallic Reagents755

22-9 Esters and Amides of Carbonic Acid756

Summary in Chinese758

Study Problems761

Chapter 23 Condensations and Alpha Substitutions of Carbonyl Compounds767

23-1 Introduction767

23-2 Enols and Enolate Ions768

23-3 Alpha Halogenation of Ketones771

23-4 α Bromination of Acids:The HVZ Reaction775

23-5 Alkylation of Enolate Ions776

23-6 Formation and Alkylation of Enamines778

23-7 The Aldol Condensation of Ketones and Aldehydes779

23-8 Dehydration of Aldol Products782

23-9 Crossed Aldol Condensations783

23-10 Aldol Cyclizations784

23-11 The Claisen Ester Condensation785

23-12 The Dieckmann Condensation:A Claisen Cyclization787

23-13 Crossed Claisen Condensations788

23-14 Syntheses Using β-Dicarbonyl Compounds791

23-15 The Malonic Ester Synthesis792

23-16 The Acetoacetic Ester Synthesis795

23-17 Conjugate Additions:The Michael Reaction797

23-18 The Robinson Annulation800

Summary in Chinese802

Study Problems805

Chapter 24 Carbohydrates and Nucleic Acids810

24-1 Introduction810

24-2 Classification of Carbohydrates811

24-3 Monosaccharides812

24-4 Erythro and Threo Diastereomers815

24-5 Epimers816

24-6 Cyclic Structures of Monosaccharides816

24-7 Anomers of Monosaccharides;Mutarotation818

24-8 Reactions of Monosaccharides:Side Reactions in Base820

24-9 Reduction of Monosaccharides822

24-10 Oxidation of Monosaccharides;Reducing Sugars823

24-11 Nonreducing Sugars:Formation of Glycosides824

24-12 Ether and Ester Formation825

24-13 Reactions with Phenylhydrazine:Osazone Formation827

24-14 Chain Shortening:The Ruff Degradation827

24-15 Chain Lengthening:The Kiliani-Fischer Synthesis828

24-16 Fischer's Proof of the Configuration of Glucose829

24-17 Determination of Ring Size;Periodic Acid Cleavage of Sugars832

24-18 Disaccharides833

24-19 Polysaccharides836

24-20 Nucleic Acids:Introduction839

24-21 Ribonucleosides and Ribonucleotides840

24-22 The Structure of Ribonucleic Acid842

24-23 Deoxyribose and the Structure of Deoxyribonucleic Acid843

24-24 Additional Functions of Nucleotides845

Summary in Chinese847

Study Problems851

Chapter 25 Amino Acids,Peptides,and Proteins855

25-1 Introduction855

25-2 Structure and Stereochemistry of the α-Amino Acids856

25-3 Acid-Base Properties of Amino Acids860

25-4 Isoelectric Points861

25-5 Synthesis of Amino Acids862

25-6 Resolution of Amino Acids865

25-7 Reactions of Amino Acids865

25-8 Structure and Nomenclature of Peptides and Proteins868

25-9 Peptide Structure Determination871

25-10 Solution-Phase Peptide Synthesis875

25-11 Solid-Phase Peptide Synthesis878

25-12 Classification of Proteins882

25-13 Levels of Protein Structure882

25-14 Protein Denaturation885

Summary in Chinese885

Study Problems889

Chapter 26 Lipids893

26-1 Introduction893

26-2 Waxes893

26-3 Triglycerides894

26-4 Saponification of Fats and Oils;Soaps and Detergents897

26-5 Phospholipids899

26-6 Steroids900

26-7 Terpenes902

Summary in Chinese905

Study Problems906

Answers to Selected Problems909

Index919

Vocabulary925