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1 Structure and Bonding: Acids and Bases1

1.1 Atomic Structure3

1.2 Electron Configuration of Atoms4

1.3 Development of Chemical Bonding Theory6

1.4 The Nature of Chemical Bonds: Ionic Bonds7

1.5 The Nature of Chemical Bonds: Covalent Bonds8

1.6 Formation of Covalent Bonds11

1.7 Hybridization: sp3 Orbitals and the Structure of Methane12

1.8 The Structure of Ethane14

1.9 Hybridization: sp2 Orbitals and the Structure of Ethylene16

1.10 Hybridization: sp Orbitals and the Structure of Acetylene18

1.11 Bond Polarity and Electronegativity20

1.12 Acids and Bases: The Br?nsted-Lowry Definition23

1.13 Acids and Bases: The Lewis Definition26

Interlude—Chemicals, Toxicity, and Risk29

Summary and Key Words30

Additional Problems31

Working Problems31

2 The Nature of Organic Compounds: Alkanes36

2.1 Functional Groups36

2.2 Alkanes and Alkyl Groups: Isomers41

2.3 Naming Branched-Chain Alkanes47

2.4 Properties of Alkanes50

2.5 Conformations of Ethane51

2.6 Drawing Chemical Structures55

2.7 Cycloalkanes57

2.8 Cis-Trans Isomerism in Cycloalkanes58

2.9 Conformations of Some Common Cycloalkanes60

2.10 Axial and Equatorial Bonds in Cyclohexane63

2.11 Conformational Mobility of Cyclohexane65

Interlude—Petroleum67

Summary and Key Words69

Additional Problems70

3 Alkenes: The Nature of Organic Reactions76

3.1 Naming Alkenes77

3.2 Electronic Structure of Alkenes79

3.3 Cis-Trans Isomers of Alkenes80

3.4 Sequence Rules: The E,Z Designation83

3.5 Kinds of Organic Reactions87

3.6 How Reactions Occur: Mechanisms88

3.7 An Example of a Polar Reaction: Addition of HCI to Ethylene91

3.8 The Mechanism of an Organic Reaction: Addition of HCI to Ethylene92

3.9 Describing a Reaction: Rates and Equilibria93

3.10 Describing a Reaction: Reaction Energy Diagrams and Transition States96

3.11 Describing a Reaction: Intermediates98

Interlude--Carrots, Alkenes, and the Chemistry of Vision100

Summary and Key Words102

Additional Problems103

4 Alkenes and Alkynes108

4.1 Addition of HX to Alkenes: Hydrohalogenation109

4.2 Orientation of Alkene Addition Reactions: Markovnikov s Rule110

4.3 Carbocation Structure and Stability112

4.4 Addition of H2O to Alkenes: Hydration114

4.5 Addition of X2 to Alkenes: Halogenation116

4.6 Addition of H2 to Alkenes: Hydrogenation118

4.7 Oxidation of Alkenes120

4.8 Alkene Polymers122

4.9 Preparation of Alkenes: Elimination Reactions124

4.10 Conjugated Dienes127

4.11 Stability of Allylic Carbocations: Resonance129

4.12 Drawing and Interpreting Resonance Forms131

4.13 Alkynes134

4.14 Reactions of Alkynes: Addition of H2, HX, and X2136

4.15 Addition of H2O to Alkynes137

4.16 Alkyne Acidity: Formation of Acetylide Anions138

Interlude—Natural Rubber140

Summary and Key Words141

Summary of Reactions142

Additional Problems145

5 Aromatic Compounds150

5.1 Structure of Benzene: The Kekule Proposal151

5.2 Stability of Benzene152

5.3 Structure of Benzene: The Resonance Proposal153

5.4 Naming Aromatic Compounds154

5.5 Chemistry of Benzene: Electrophilic Aromatic Substitution Reactions157

5.6 Bromination of Benzene158

5.7 Other Electrophilic Aromatic Substitution Reactions160

5.8 The Friedel-Crafts Alkylation and Acylation Reactions163

5.9 Substituent Effects in Electrophilic Aromatic Substitution164

5.10 An Explanation of Substituent Effects166

5.11 Oxidation and Reduction of Aromatic Compounds170

5.12 Polycyclic Aromatic Hydrocarbons171

5.13 Organic Synthesis172

Interlude—Aspirin and Other Aromatic NSAID s175

Summary and Key Words176

Summary of Reactions177

Additional Problems178

6 Stereochemistry183

6.1 Stereochemistry and the Tetrahedral Carbon183

6.2 The Reason for Handedness in Molecules: Chirality185

6.3 Optical Activity190

6.4 Specific Rotation191

6.5 Pasteur s Discovery of Enantiomers192

6.6 Sequence Rules for Specifying Configuration193

6.7 Diastereomers196

6.8 Meso Compounds198

6.9 Molecules with More Than Two Stereocenters200

6.10 Racemic Mixtures and the Resolution of Enantiomers201

6.11 Physical Properties of Stereoisomers204

6.12 A Brief Review of Isomerism205

6.13 Stereochemistry of Reactions: Addition of HBr to Alkenes206

6.14 Chirality in Nature208

Interlude—Chiral Drugs209

Summary and Key Words211

Additional Problems211

7 Alkyl Halides217

7.1 Naming Alkyl Halides218

7.2 Preparation of Alkyl Halides: Radical Chlorination of Alkanes219

7.3 Alkyl Halides from Alcohols222

7.4 Reactions of Alkyl Halides: Grignard Reagents223

7.5 Nucleophilic Substitution Reactions: The Discovery225

7.6 Kinds of Nucleophilic Substitution Reactions226

7.7 The SN2 Reaction228

7.8 The SN1 Reaction232

7.9 Eliminations: The E2 Reaction236

7.10 Eliminations: The E1 Reaction239

7.11 A Summary of Reactivity: SN1, SN2, E1, E2239

7.12 Substitution Reactions in Living Organisms242

Interlude—Naturally Occurring Organohalogen Compounds243

Summary and Key Words244

Summary of Reactions245

Additional Problems246

8 Alcohols,Ethers,and Phenols251

8.1 Naming Alcohols, Phenols, and Ethers252

8.2 Properties of Alcohols, Phenols, and Ethers: Hydrogen Bonding254

8.3 Properties of Alcohols and Phenols: Acidity256

8.4 Synthesis of Alcohols258

8.5 Alcohols from Carbonyl Compounds259

8.6 Ethers from Alcohols: The Williamson Ether Synthesis261

8.7 Reactions of Alcohols263

8.8 Synthesis and Reactions of Phenols265

8.9 Reactions of Ethers: Acidic Cleavage267

8.10 Cyclic Ethers: Epoxides268

8.11 Ring-Opening Reactions of Epoxides269

8.12 Thiols and Sulfides270

Interlude—Ethanol as Chemical, Drug, and Poison272

Summary and Key Words274

Summary of Reactions275

Additional Problems276

9 Aldehydes and Ketones: Nucleophilic Addition Reactions281

9.1 Kinds of Carbonyl Compounds282

9.2 Structure and Properties of Carbonyl Groups283

9.3 Naming Aldehydes and Ketones284

9.4 Synthesis of Aldehydes and Ketones286

9.5 Oxidation of Aldehydes287

9.6 Reactions of Aldehydes and Ketones: Nucleophilic Additions288

9.7 Nucleophilic Addition of Water: Hydration290

9.8 Nucleophilic Addition of Alcohols: Acetal Formation293

9.9 Nucleophilic Addition of Amines: Imine Formation295

9.10 Nucleophilic Addition of Grignard Reagents: Alcohol Formation296

9.11 Some Biological Nucleophilic Addition Reactions299

Interlude—Insect Antifeedants300

Summary and Key Words301

Summary of Reactions302

Additional Problems303

10 Carboxylic Acids and Derivatives308

10.1 Naming Carboxylic Acids and Derivatives309

10.2 Occurrence, Structure, and Properties of Carboxylic Acids313

10.3 Acidity of Carboxylic Acids313

10.4 Synthesis of Carboxylic Acids316

10.5 Nucleophilic Acyl Substitution Reactions318

10.6 Reactions of Carboxylic Acids321

10.7 Chemistry of Acid Halides325

10.8 Chemistry of Acid Anhydrides327

10.9 Chemistry of Esters329

10.10 Chemistry of Amides334

10.11 Chemistry of Nitriles336

10.12 Nylons and Polyesters: Step-Growth Polymers339

Interlude—β-Lactam Antibiotics342

Summary and Key Words343

Summary of Reactions344

Additional Problems346

11 Carbonyl Alpha-Substitution Reactions and Condensation Reactions352

11.1 Keto-Enol Tautomerism353

11.2 Reactivity of Enols: The Mechanism of Alpha-Substitution Reactions356

11.3 Alpha Halogenation of Aldehydes and Ketones356

11.4 Acidity of Alpha Hydrogen Atoms: Enolate Ion Formation358

11.5 Reactivity of Enolate Ions362

11.6 Alkylation of Enolate Ions362

11.7 Carbonyl Condensation Reactions365

11.8 Condensations of Aldehydes and Ketones: The Aldol Reaction366

11.9 Dehydration of Aldol Products: Synthesis of Enones368

11.10 Condensations of Esters: The Claisen Condensation Reaction369

Interlude—Carbonyl Compounds in Metabolism372

Summary and Key Words373

Summary of Reactions374

Additional Problems375

12 Amines380

12.1 Naming Amines381

12.2 Structure and Properties of Amines383

12.3 Amine Basicity384

12.4 Synthesis of Amines387

12.5 Reactions of Amines390

12.6 Heterocyclic Amines394

Interlude—Naturally Occurring Amines: Morphine Alkaloids398

Summary and Key Words400

Summary of Reactions401

Additional Problems402

13 Structure Determination406

13.1 Infrared Spectroscopy and the Electromagnetic Spectrum407

13.2 Infrared Spectroscopy of Organic Molecules410

13.3 Ultraviolet Spectroscopy415

13.4 Interpreting Ultraviolet Spectra: The Effect of Conjugation416

13.5 Nuclear Magnetic Resonance Spectroscopy418

13.6 The Nature of NMR Absorptions419

13.7 Chemical Shifts421

13.8 Chemical Shifts in 1H NMR Spectra423

13.9 Integration of 1H NMR Spectra: Proton Counting424

13.10 Spin-Spin Splitting in 1H NMR Spectra425

13.11 Uses of 1H NMR Spectra429

13.12 13C NMR Spectroscopy430

Interlude—Magnetic Resonance Imaging (MRI)432

Summary and Key Words433

Additional Problems434

14 Biomolecules: Carbohydrates440

14.1 Classification of Carbohydrates441

14.2 Configurations of Monosaccharides: Fischer Projections443

14.3 D,L Sugars445

14.4 Configurations of Aldoses447

14.5 Cyclic Structures of Monosaccharides: Hemiacetal Formation448

14.6 Monosaccharide Anomers: Mutarotation452

14.8 Reactions of Monosaccharides454

14.7 Conformations of Monosaccharides454

14.9 Disaccharides460

14.10 Polysaccharides462

14.11 Other Important Carbohydrates465

14.12 Cell-Surface Carbohydrates466

Interlude—Sweetness468

Summary and Key Words469

Additional Problems470

15 Biomolecules: Amino Acids,Peptides, and Proteins474

15.1 Structures of Amino Acids475

15.2 Dipolar Structure of Amino Acids478

15.3 Isoelectric Points480

15.4 Peptides and Proteins481

15.5 Covalent Bonding in Peptides484

15.6 Peptide Structure Determination: Amino Acid Analysis484

15.7 Peptide Sequencing: The Edman Degradation486

15.8 Peptide Synthesis488

15.9 Classification of Proteins491

15.10 Protein Structure493

15.11 Enzymes497

15.12 Structure and Classification of Enzymes497

Interlude—Protein and Nutrition500

Summary and Key Words501

Additional Problems502

16.1 Lipids507

16 Biomolecules: Lipids and Nucleic Acids507

16.2 Fats and Oils508

16.3 Soaps511

16.4 Phospholipids513

16.5 Steroids515

16.6 Nucleic Acids and Nucleotides517

16.7 Structure of DNA519

16.8 Base Pairing in DNA: The Watson-Crick Model522

16.10 Replication of DNA525

16.9 Nucleic Acids and Heredity525

16.11 Structure and Synthesis of RNA: Transcription527

16.12 RNA and Protein Biosynthesis: Translation528

16.13 Sequencing DNA532

16.14 The Polymerase Chain Reaction536

Interlude—Cholesterol and Heart Disease538

Summary and Key Words539

Additional Problems540

17 The Organic Chemistry of Metabolic Pathways543

17.1 An Overview of Metabolism and Biochemical Energy543

17.2 Catabolism of Fats: β-Οxidation Pathway547

17.3 Catabolism of Carbohydretes: Glycolysis552

17.4 The Citric Acid Cycle557

17.5 Catabolism of Proteins: Transamination560

Interlude—Basal Metabolism562

Summary and Key Words563

Additional Problems564