دانلود کتاب Organic Chemistry, 07th Edition

فهرست مطالب :

Preface xx

  Acknowledgments xxvii



  Prologue 1

  What Is Organic Chemistry? 1

  Some Representative Molecules 2

  The Marine Environment 4

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1 Structure and Bonding 5

1.1 The Periodic Table 6

1.2   Bonding 8

1.3   Lewis Structures 10

1.4   Isomers 15

1.5   Exceptions to the Octet Rule 16

1.6   Resonance 16

1.7   Determining Molecular Shape 23

1.8   Drawing Organic Structures 27

1.9   Hybridization 33

1.10 Ethane, Ethylene, and Acetylene 36

1.11 Bond Length and Bond Strength 41

1.12 Electronegativity and Bond Polarity 42

1.13 Polarity of Molecules 44

1.14 Oxybenzone—A Representative Organic Molecule 45

   Chapter 1 Review 47

   Key Concepts 47

   Key Skills 48

   Multiple-Choice Self-Test 50

   Problems 51

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2 Acids and Bases 57

2.1 Brønsted–Lowry Acids and Bases 58

2.2 Reactions of Brønsted–Lowry Acids and Bases 59

2.3 Acid Strength and pKa 62

2.4 Predicting the Outcome of Acid–Base Reactions 65

2.5 Factors That Determine Acid Strength 66

2.6 Common Acids and Bases 76

2.7 Aspirin 77

2.8 Lewis Acids and Bases 78

  Chapter 2 Review 81

  Key Concepts 81

  Key Skills 82

  Multiple-Choice Self-Test 84

  Problems 85

Page vi

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3 Introduction to Organic Molecules and Functional Groups 92

3.1 Functional Groups 93

3.2 An Overview of Functional Groups 94

3.3 Intermolecular Forces 101

3.4 Physical Properties 104

3.5 Application: Vitamins 111

3.6 Application of Solubility: Soap 112

3.7 Application: The Cell Membrane 113

3.8 Functional Groups and Reactivity 116

3.9 Biomolecules 118

  Chapter 3 Review 119

  Key Concepts 119

  Key Skills 121

  Multiple-Choice Self-Test 122

  Problems 123

Daniel C. Smith

4 Alkanes 130

4.1 Alkanes—An Introduction 131

4.2 Cycloalkanes 133

4.3 An Introduction to Nomenclature 134

4.4 Naming Alkanes 135

4.5 Naming Cycloalkanes 141

4.6 Natural Occurrence of Alkanes 142

4.7 Properties of Alkanes 144

4.8 Conformations of Acyclic Alkanes—Ethane 145

4.9 Conformations of Butane 148

4.10 An Introduction to Cycloalkanes 152

4.11 Cyclohexane 153

4.12 Substituted Cycloalkanes 156

4.13 Oxidation of Alkanes 162

4.14 Lipids—Part 1 165

   Chapter 4 Review 167

   Key Concepts 167

   Key Skills 169

   Multiple-Choice Self-Test 171

   Problems 172

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5 Stereochemistry 178

5.1 Starch and Cellulose 179

5.2 The Two Major Classes of Isomers 181

5.3 Looking Glass Chemistry—Chiral and Achiral Molecules 181

5.4 Stereogenic Centers 184

5.5 Stereogenic Centers in Cyclic Compounds 188

5.6 Labeling Stereogenic Centers with R or S 190

5.7 Disastereomers 195

5.8 Meso Compounds 197

5.9 R and S Assignments in Compounds with Two or More Stereogenic Centers 199

5.10 Disubstituted Cycloalkanes 199

5.11 Isomers—A Summary 201

5.12 Physical Properties of Stereoisomers 202

5.13 Chemical Properties of Enantiomers 206

    Chapter 5 Review 209

    Key Concepts 209

    Key Skills 210

    Multiple-Choice Self-Test 212

    Problems 213

Page vii

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6 Understanding Organic Reactions 220

6.1 Writing Equations for Organic Reactions 221

6.2 Kinds of Organic Reactions 222

6.3 Bond Breaking and Bond Making 224

6.4 Bond Dissociation Energy 228

6.5 Thermodynamics 231

6.6 Enthalpy and Entropy 233

6.7 Energy Diagrams 235

6.8 Energy Diagram for a Two-Step Reaction Mechanism 237

6.9 Kinetics 239

6.10 Catalysts 242

6.11 Enzymes 243

    Chapter 6 Review 244

    Key Concepts 244

    Key Equations 245

    Key Skills 245

    Multiple-Choice Self-Test 246

    Problems 247

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7 Alkyl Halides and Nucleophilic Substitution 253

7.1   Introduction to Alkyl Halides 254

7.2   Nomenclature 255

7.3   Properties of Alkyl Halides 256

7.4   Interesting Alkyl Halides 256

7.5   The Polar Carbon–Halogen Bond 258

7.6   General Features of Nucleophilic Substitution 259

7.7   The Leaving Group 261

7.8   The Nucleophile 263

7.9   The Mechanisms for Nucleophilic Substitution 266

7.10 The SN2 Mechanism 268

7.11 The SN1 Mechanism 274

7.12 Carbocation Stability 278

7.13 The Hammond Postulate 279

7.14 When Is the Mechanism SN1 or SN2? 282

7.15 Biological Nucleophilic Substitution 288

7.16 Vinyl Halides and Aryl Halides 291

7.17 Organic Synthesis 291

     Chapter 7 Review 293

     Key Concepts 293

     Key Skills 295

     Key Mechanism Concepts 296

     Multiple-Choice Self-Test 297

     Problems 298

Page viii

Forest & Kim Starr

8 Alkyl Halides and Elimination Reactions 305

8.1 General Features of Elimination 306

8.2 Alkenes—The Products of Elimination Reactions 307

8.3 The Mechanisms of Elimination 311

8.4 The E2 Mechanism 311

8.5 The Zaitsev Rule 314

8.6 Stereochemistry of the E2 Reaction 316

8.7 The E1 Mechanism 320

8.8 SN1 and E1 Reactions 323

8.9 When Is the Mechanism E1 or E2? 324

8.10 E2 Reactions and Alkyne Synthesis 324

8.11 When Is the Reaction SN1, SN2, E1, or E2? 326

     Chapter 8 Review 330

     Key Concepts 330

     Key Skills 331

     Key Mechanism Concepts 333

     Multiple-Choice Self-Test 334

     Problems 335

Jill Braaten/McGraw Hill

9 Alcohols, Ethers, and Related Compounds 342

9.1 Introduction 343

9.2 Structure and Bonding 344

9.3 Nomenclature 344

9.4 Properties of Alcohols, Ethers, and Epoxides 348

9.5 Interesting Alcohols, Ethers, and Epoxides 349

9.6 Preparation of Alcohols, Ethers, and Epoxides 350

9.7 General Features—Reactions of Alcohols, Ethers, and Epoxides 353

9.8 Dehydration of Alcohols to Alkenes 354

9.9 Carbocation Rearrangements 357

9.10 Dehydration Using POCl3 and Pyridine 359

9.11 Conversion of Alcohols to Alkyl Halides with HX 361

9.12 Conversion of Alcohols to Alkyl Halides with SOCl2 and PBr3 364

9.13 Tosylate—Another Good Leaving Group 367

9.14 Reaction of Ethers with Strong Acid 370

9.15 Thiols and Sulfides 371

9.16 Reactions of Epoxides 374

9.17 Application: Epoxides, Leukotrienes, and Asthma 378

9.18 Application: Benzo[α]pyrene, Epoxides, and Cancer 380

     Chapter 9 Review 380

     Key Concepts 380

     Key Reactions 381

     Key Skills 382

     Key Mechanism Concepts in Reactions of Alcohols 384

     Multiple-Choice Self-Test 385

     Problems 386

Page ix

McGraw Hill

10 Alkenes and Addition Reactions 393

10.1 Introduction 394

10.2 Calculating Degrees of Unsaturation 395

10.3 Nomenclature 397

10.4 Properties of Alkenes 401

10.5 Interesting Alkenes 402

10.6 Lipids—Part 2 403

10.7 Preparation of Alkenes 405

10.8 Introduction to Addition Reactions 405

10.9 Hydrohalogenation—Electrophilic Addition of HX 407

10.10 Markovnikov’s Rule 408

10.11 Stereochemistry of Electrophilic Addition of HX 410

10.12 Hydration—Electrophilic Addition of Water 412

10.13 Halogenation—Addition of Halogen 413

10.14 Stereochemistry of Halogenation 414

10.15 Halohydrin Formation 416

10.16 Hydroboration–Oxidation 419

10.17 Keeping Track of Reactions 423

10.18 Alkenes in Organic Synthesis 425

    Chapter 10 Review 427

    Key Concepts 427

    Key Reactions 428

    Key Skills 428

    Key Mechanism Concepts 429

    Multiple-Choice Self-Test 430

    Problems 431

McGraw Hill

11 Alkynes and Synthesis 436

11.1 Introduction 437

11.2 Nomenclature 438

11.3 Properties of Alkynes 439

11.4 Interesting Alkynes 439

11.5 Preparation of Alkynes 441

11.6 Introduction to Alkyne Reactions 441

11.7 Addition of Hydrogen Halides 443

11.8 Addition of Halogen 445

11.9 Addition of Water 446

11.10 Hydroboration–Oxidation 448

11.11 Reaction of Acetylide Anions 450

11.12 Synthesis 454

     Chapter 11 Review 457

    Key Reactions 457

    Key Skills 457

    Multiple-Choice Self-Test 459

    Problems 461

Page x

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12 Oxidation and Reduction 466

12.1 Introduction 467

12.2 Reducing Agents 468

12.3 Reduction of Alkenes 469

12.4 Application: Hydrogenation of Oils 472

12.5 Reduction of Alkynes 474

12.6 The Reduction of Polar C─X σ Bonds 477

12.7 Oxidizing Agents 478

12.8 Epoxidation 479

12.9 Dihydroxylation 482

12.10 Oxidative Cleavage of Alkenes 485

12.11 Oxidative Cleavage of Alkynes 487

12.12 Oxidation of Alcohols 488

12.13 Green Chemistry 491

12.14 Biological Oxidation 492

12.15 Sharpless Epoxidation 493

      Chapter 12 Review 496

      Key Concepts 496

      Key Reactions 497

      Key Skills 498

      Multiple-Choice Self-Test 499

      Problems 501

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Spectroscopy A Mass Spectrometry 507

A.1 Mass Spectrometry and the Molecular Ion 508

A.2 Alkyl Halides and the M + 2 Peak 513

A.3 Fragmentation 515

A.4 Fragmentation Patterns of Some Common Functional Groups 518

A.5 Other Types of Mass Spectrometry 520

    Chapter Review 523

    Key Concepts 523

    Key Skills 523

    Multiple-Choice Self-Test 524

    Problems 524

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Page xi

Spectroscopy B Infrared Spectroscopy 529

B.1 Electromagnetic Radiation 530

B.2 The General Features of Infrared Spectroscopy 532

B.3 IR Absorptions 534

B.4 Infrared Spectra of Common Functional Groups 540

B.5 IR and Structure Determination 547

    Chapter Review 549

    Key Concepts 549

    Key Skills 550

    Multiple-Choice Self-Test 551

    Problems 552

Daniel C. Smith

Spectroscopy C Nuclear Magnetic Resonance Spectroscopy 557

C.1 An Introduction to NMR Spectroscopy 558

C.2 1H NMR: Number of Signals 561

C.3 1H NMR: Position of Signals 566

C.4 The Chemical Shifts of Protons on sp2 and sp Hybridized Carbons 570

C.5 1H NMR: Intensity of Signals 572

C.6 1H NMR: Spin–Spin Splitting 573

C.7 More-Complex Examples of Splitting 577

C.8 Spin–Spin Splitting in Alkenes 580

C.9 Other Facts About 1H NMR Spectroscopy 582

C.10 Using 1H NMR to Identify an Unknown 585

C.11 13C NMR Spectroscopy 588

C.12 Magnetic Resonance Imaging (MRI) 591

    Chapter Review 592

    Key Concepts 592

    Key Skills 593

    Multiple-Choice Self-Test 596

    Problems 597

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13 Radical Reactions 606

13.1 Introduction 607

13.2 General Features of Radical Reactions 608

13.3 Halogenation of Alkanes 610

13.4 The Mechanism of Halogenation 611

13.5 Chlorination of Other Alkanes 614

13.6 Chlorination Versus Bromination 614

13.7 Halogenation as a Tool in Organic Synthesis 617

13.8 The Stereochemistry of Halogenation Reactions 618

13.9 Application: The Ozone Layer and CFCs 620

13.10 Radical Halogenation at an Allylic Carbon 622

13.11 Application: Oxidation of Unsaturated Lipids 625

13.12 Application: Antioxidants 626

13.13 Radical Addition Reactions to Double Bonds 627

13.14 Polymers and Polymerization 630

   Chapter 13 Review 633

   Key Concepts 633

   Key Reactions 633

   Key Skills 634

   Multiple-Choice Self-Test 636

   Problems 637

Page xii

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14 Conjugation, Resonance, and Dienes 645

14.1 Conjugation 646

14.2 Resonance and Allylic Carbocations 648

14.3 Common Examples of Resonance 649

14.4 The Resonance Hybrid 651

14.5 Electron Delocalization, Hybridization, and Geometry 653

14.6 Conjugated Dienes 654

14.7 Interesting Dienes and Polyenes 655

14.8 The Carbon–Carbon σ Bond Length in Buta-1,3-diene 656

14.9 Stability of Conjugated Dienes 657

14.10 Electrophilic Addition: 1,2- Versus 1,4-Addition 658

14.11 Kinetic Versus Thermodynamic Products 660

14.12 The Diels–Alder Reaction 663

14.13 Specific Rules Governing the Diels–Alder Reaction 664

14.14 Other Facts About the Diels–Alder Reaction 669

14.15 Conjugated Dienes and Ultraviolet Light 672

   Chapter 14 Review 674

   Key Concepts 674

   Key Reactions 675

   Key Skills 676

   Multiple-Choice Self-Test 678

   Problems 679

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15 Benzene and Aromatic Compounds 686

15.1 Background 687

15.2 The Structure of Benzene 688

15.3 Nomenclature of Benzene Derivatives 690

15.4 Spectroscopic Properties 692

15.5 Interesting Aromatic Compounds 693

15.6 Benzene’s Unusual Stability 694

15.7 The Criteria for Aromaticity—Hückel’s Rule 696

15.8 Examples of Aromatic Compounds 698

15.9 Aromatic Heterocycles 701

15.10 What Is the Basis of Hückel’s Rule? 706

15.11 The Inscribed Polygon Method for Predicting Aromaticity 708

   Chapter 15 Review 711

   Key Concepts 711

   Key Skills 712

   Multiple-Choice Self-Test 713

   Problems 714

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Page xiii

16 Reactions of Aromatic Compounds 722

16.1 Electrophilic Aromatic Substitution 723

16.2 The General Mechanism 724

16.3 Halogenation 725

16.4 Nitration and Sulfonation 727

16.5 Friedel–Crafts Alkylation and Friedel–Crafts Acylation 729

16.6 Substituted Benzenes 736

16.7 Electrophilic Aromatic Substitution of Substituted Benzenes 739

16.8 Why Substituents Activate or Deactivate a Benzene Ring 743

16.9 Orientation Effects in Substituted Benzenes 744

16.10 Limitations on Electrophilic Substitution Reactions with Substituted Benzenes 748

16.11 Disubstituted Benzenes 750

16.12 Synthesis of Benzene Derivatives 752

16.13 Nucleophilic Aromatic Substitution 753

16.14 Reactions of Substituted Benzenes 757

16.15 Multistep Synthesis 762

   Chapter 16 Review 764

   Key Concepts 764

   Key Reactions 765

   Key Skills 766

   Key Mechanism Concepts 767

   Multiple-Choice Self-Test 768

   Problems 769

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17 Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction 777

17.1 Introduction 778

17.2 General Reactions of Carbonyl Compounds 779

17.3 A Preview of Oxidation and Reduction 782

17.4 Reduction of Aldehydes and Ketones 784

17.5 The Stereochemistry of Carbonyl Reduction 786

17.6 Enantioselective Carbonyl Reductions 787

17.7 Reduction of Carboxylic Acids and Their Derivatives 790

17.8 Oxidation of Aldehydes 795

17.9 Organometallic Reagents 796

17.10 Reaction of Organometallic Reagents with Aldehydes and Ketones 799

17.11 Retrosynthetic Analysis of Grignard Products 803

17.12 Protecting Groups 805

17.13 Reaction of Organometallic Reagents with Carboxylic Acid Derivatives 807

17.14 Reaction of Organometallic Reagents with Other Compounds 811

17.15 α,β-Unsaturated Carbonyl Compounds 812

17.16 Summary—The Reactions of Organometallic Reagents 815

17.17 Synthesis 815

   Chapter 17 Review 818

   Key Reactions 818

   Key Skills 821

   Key Mechanism Concepts 822

   Multiple-Choice Self-Test 823

   Problems 824

Page xiv

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18 Aldehydes and Ketones—Nucleophilic Addition 832

18.1 Introduction 833

18.2 Nomenclature 834

18.3 Properties of Aldehydes and Ketones 838

18.4 Interesting Aldehydes and Ketones 840

18.5 Preparation of Aldehydes and Ketones 840

18.6 Reactions of Aldehydes and Ketones—General Considerations 842

18.7 Nucleophilic Addition of H– and R–—A Review 845

18.8 Nucleophilic Addition of –CN 846

18.9 The Wittig Reaction 848

18.10 Addition of 1° Amines 854

18.11 Addition of 2° Amines 856

18.12 Addition of H2O—Hydration 860

18.13 Addition of Alcohols—Acetal Formation 862

18.14 Acetals as Protecting Groups 867

18.15 Cyclic Hemiacetals 868

18.16 An Introduction to Carbohydrates 871

   Chapter 18 Review 873

   Key Concepts 873

   Key Reactions 873

   Key Skills 874

   Multiple-Choice Self-Test 876

   Problems 877

Daniel C. Smith

19 Carboxylic Acids and Nitriles 888

19.1 Structure and Bonding 889

19.2 Nomenclature 890

19.3 Physical and Spectroscopic Properties 893

19.4 Interesting Carboxylic Acids and Nitriles 894

19.5 Aspirin, Arachidonic Acid, and Prostaglandins 895

19.6 Preparation of Carboxylic Acids 897

19.7 Carboxylic Acids—Strong Organic Brønsted–Lowry Acids 898

19.8 Inductive Effects in Aliphatic Carboxylic Acids 901

19.9 Substituted Benzoic Acids 903

19.10 Extraction 905

19.11 Amino Acids 908

19.12 Nitriles 911

   Chapter 19 Review 916

   Key Concepts 916

   Key Reactions 917

   Key Skills 917

   Multiple-Choice Self-Test 918

   Problems 920

Page xv

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20 Carboxylic Acids and Their Derivatives—Nucleophilic Acyl Substitution 928

20.1 Introduction 929

20.2 Structure and Bonding 931

20.3 Nomenclature 932

20.4 Physical and Spectroscopic Properties 936

20.5 Interesting Esters and Amides 938

20.6 Introduction to Nucleophilic Acyl Substitution 939

20.7 Reactions of Acid Chlorides 943

20.8 Reactions of Anhydrides 945

20.9 Reactions of Carboxylic Acids 946

20.10 Reactions of Esters 952

20.11 Application: Lipid Hydrolysis 954

20.12 Reactions of Amides 956

20.13 Application: The Mechanism of Action of β-Lactam Antibiotics 957

20.14 Summary of Nucleophilic Acyl Substitution Reactions 958

20.15 Natural and Synthetic Fibers 959

20.16 Biological Acylation Reactions 961

   Chapter 20 Review 963

   Key Concepts 963

   Key Reactions 963

   Key Skills 965

   Multiple-Choice Self-Test 966

   Problems 967

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21 Substitution Reactions of Carbonyl Compounds at the α Carbon 976

21.1 Introduction 977

21.2 Enols 977

21.3 Enolates 981

21.4 Enolates of Unsymmmetrical Carbonyl Compounds 985

21.5 Racemization at the α Carbon 987

21.6 A Preview of Reactions at the α Carbon 988

21.7 Halogenation at the α Carbon 989

21.8 Direct Enolate Alkylation 993

21.9 Malonic Ester Synthesis 996

21.10 Acetoacetic Ester Synthesis 1001

   Chapter 21 Review 1004

   Key Reactions 1004

   Key Skills 1005

   Multiple-Choice Self-Test 1006

   Problems 1008

Page xvi

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22 Carbonyl Condensation Reactions 1015

22.1 The Aldol Reaction 1016

22.2 Crossed Aldol Reactions 1021

22.3 Directed Aldol Reactions 1025

22.4 Intramolecular Aldol Reactions 1027

22.5 The Claisen Reaction 1030

22.6 The Crossed Claisen and Related Reactions 1032

22.7 The Dieckmann Reaction 1034

22.8 The Michael Reaction 1035

22.9 The Robinson Annulation 1037

   Chapter 22 Review 1041

   Key Reactions 1041

   Key Skills 1042

   Multiple-Choice Self-Test 1043

   Problems 1045

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23 Amines 1053

23.1 Introduction 1054

23.2 Structure and Bonding 1054

23.3 Nomenclature 1055

23.4 Physical and Spectroscopic Properties 1058

23.5 Interesting and Useful Amines 1059

23.6 Preparation of Amines 1062

23.7 Reactions of Amines—General Features 1068

23.8 Amines as Bases 1069

23.9 Relative Basicity of Amines and Other Compounds 1071

23.10 Amines as Nucleophiles 1077

23.11 Hofmann Elimination 1079

23.12 Reactions of Amines with Nitrous Acid 1082

23.13 Substitution Reactions of Aryl Diazonium Salts 1083

23.14 Coupling Reactions of Aryl Diazonium Salts 1088

23.15 Application: Synthetic Dyes and Sulfa Drugs 1090

   Chapter 23 Review 1093

   Key Concepts 1093

   Key Reactions 1093

   Key Skills 1095

   Multiple-Choice Self-Test 1096

   Problems 1098

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24 Carbon–Carbon Bond-Forming Reactions in Organic Synthesis 1106

24.1 Coupling Reactions of Organocuprate Reagents 1107

24.2 Suzuki Reaction 1109

24.3 Heck Reaction 1114

24.4 Stille Coupling 1116

24.5 Carbenes and Cyclopropane Synthesis 1119

24.6 Simmons–Smith Reaction 1122

24.7 Metathesis 1123

    Chapter 24 Review 1128

    Key Reactions 1128

    Key Skills 1129

    Multiple-Choice Self-Test 1131

    Problems 1132

Page xvii

Ron Nichols/USDA Natural Resources Conservation Service

25 Pericyclic Reactions 1141

25.1 Types of Pericyclic Reactions 1142

25.2 Molecular Orbitals 1143

25.3 Electrocyclic Reactions 1146

25.4 Cycloaddition Reactions 1152

25.5 Sigmatropic Rearrangements 1156

25.6 Summary of Rules for Pericyclic Reactions 1162

    Chapter 25 Review 1163

    Key Concepts 1163

    Key Reactions 1163

    Key Skills 1164

    Multiple-Choice Self-Test 1165

    Problems 1166

Daniel C. Smith

26 Carbohydrates 1174

26.1 Introduction 1175

26.2 Monosaccharides 1176

26.3 The Family of d-Aldoses 1182

26.4 The Family of d-Ketoses 1183

26.5 The Cyclic Forms of Monosaccharides 1184

26.6 Glycosides 1192

26.7 Reactions of Monosaccharides at the OH Groups 1195

26.8 Reactions at the Carbonyl Group—Oxidation and Reduction 1196

26.9 Reactions at the Carbonyl Group—Adding or Removing One Carbon Atom 1199

26.10 Disaccharides 1202

26.11 Polysaccharides 1205

26.12 Other Important Sugars and Their Derivatives 1208

   Chapter 26 Review 1210

   Key Reactions 1210

   Key Skills 1211

   Multiple-Choice Self-Test 1214

   Problems 1216

Daniel C. Smith

27 Amino Acids and Proteins 1222

27.1 Amino Acids 1223

27.2 Separation of Amino Acids 1227

27.3 Enantioselective Synthesis of Amino Acids 1230

27.4 Peptides 1232

27.5 Peptide Sequencing 1236

27.6 Peptide Synthesis 1240

27.7 Automated Peptide Synthesis 1245

27.8 Protein Structure 1247

27.9 Important Proteins 1253

27.10 Enzymes 1255

   Chapter 27 Review 1258

   Key Reactions 1258

   Key Skills 1259

   Multiple-Choice Self-Test 1261

   Problems 1262

Page xviii

Daniel C. Smith

28 Nucleic Acids and Protein Synthesis 1268

28.1 Nucleosides and Nucleotides 1269

28.2 Nucleic Acids 1273

28.3 The DNA Double Helix 1274

28.4 Replication 1277

28.5 Ribonucleic Acids and Transcription 1278

28.6 The Genetic Code, Translation, and Protein Synthesis 1280

28.7 DNA Sequencing 1283

28.8 The Polymerase Chain Reaction 1285

28.9 Viruses 1286

    Chapter 28 Review 1288

    Key Concepts 1288

    Key Skills 1288

    Multiple-Choice Self-Test 1290

    Problems 1291

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29 Lipids 1295 (Available Online)

29.1 Introduction 1296

29.2 Waxes 1297

29.3 Triacylglycerols 1297

29.4 Phospholipids 1302

29.5 Fat-Soluble Vitamins 1304

29.6 Eicosanoids 1304

29.7 Terpenes 1308

29.8 Steroids 1314

    Chapter 29 Review 1319

    Key Concepts 1319

    Key Reactions 1320

    Key Skills 1321

    Multiple-Choice Self-Test 1321

    Problems 1322

Page xix

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30 Metabolism 1328 (Available Online)

30.1 ATP and Coupled Reactions 1329

30.2 Overview of Metabolism 1330

30.3 Key Oxidizing and Reducing Agents in Metabolism 1332

30.4 The Catabolism of Triacylglycerols by β-Oxidation 1336

30.5 The Catabolism of Carbohydrates—Glycolysis 1339

30.6 The Fate of Pyruvate 1344

30.7 The Citric Acid Cycle and ATP Production 1346

    Chapter 30 Review 1351

    Key Concepts 1351

    Key Skills 1353

    Multiple-Choice Self-Test 1353

    Problems 1354

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31 Synthetic Polymers 1358 (Available online)

31.1 Introduction 1359

31.2 Chain-Growth Polymers—Addition Polymers 1360

31.3 Anionic Polymerization of Epoxides 1366

31.4 Ziegler–Natta Catalysts and Polymer Stereochemistry 1367

31.5 Natural and Synthetic Rubbers 1368

31.6 Step-Growth Polymers—Condensation Polymers 1370

31.7 Polymer Structure and Properties 1375

31.8 Green Polymer Synthesis 1377

31.9 Polymer Recycling and Disposal 1379

    Chapter 31 Review 1382

    Key Concepts 1382

    Key Reactions 1383

    Key Skills 1383

    Multiple-Choice Self-Test 1384

    Problems 1385

Appendix A Periodic Table of the Elements A-1

Appendix B Common Abbreviations, Arrows, and Symbols A-2

Appendix C pKa Values for Selected Compounds A-4

Appendix D Nomenclature A-6

Appendix E Bond Dissociation Energies for Some Common Bonds [A—B → A• + •B] A-10

Appendix F Reactions That Form Carbon–Carbon Bonds A-11

Appendix G Characteristic IR Absorption Frequencies A-12

Appendix H Characteristic NMR Absorptions A-13

Appendix I General Types of Organic Reactions A-15

Appendix J How to Synthesize Particular Functional Groups A-17

Glossary G-1

Index I-1