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01 Covalent Bonding and Shapes of Molecules 1
1.1 How Do We Describe the Electronic Structure of Atoms? 2
1.2 What Is the Lewis Model of Bonding? 5
1.3 How Do We Predict Bond Angles and the Shapes of Molecules? 14
1.4 How Do We Predict If a Molecule Is Polar or Nonpolar? 18
1.5 What Is Resonance? 19
1.6 What Is the Orbital Overlap Model of Covalent Bonding? 22
1.7 What Are Functional Groups? 28
Summary of Key Questions 32
Quick Quiz 34
Problems 35
Looking Ahead 40
Group Learning Activities 40
CHEMICAL CONNECTIONS
1A Buckyball: A New Form of Carbon 17
02 Acids and Bases 41
2.1 What Are Arrhenius Acids and Bases? 42
2.2 What Are Brønsted–Lowry Acids and Bases? 43
2.3 How Do We Measure the Strength of an Acid or Base? 46
2.4 How Do We Determine the Position of Equilibrium in an Acid–Base Reaction? 48
2.5 What Are the Relationships between Acidity and Molecular Structure? 50
2.6 What Are Lewis Acids and Bases? 54
Summary of Key Questions 57
Quick Quiz 58
Key Reactions 59
Problems 59
Looking Ahead 62
Group Learning Activities 62
03 Alkanes and Cycloalkanes 63
3.1 What Are Alkanes? 64
3.2 What Is Constitutional Isomerism in Alkanes? 66
3.3 How Do We Name Alkanes? 69
3.4 What Are Cycloalkanes? 73
3.5 What Is the IUPAC System of Nomenclature? 75
3.6 What Are the Conformations of Alkanes and Cycloalkanes? 76
3.7 What Is Cis–Trans Isomerism in Cycloalkanes? 83
3.8 What Are the Physical Properties of Alkanes and Cycloalkanes? 87
3.9 What Are the Characteristic Reactions of Alkanes? 91
3.10 What Are the Sources of Alkanes? 91
Summary of Key Questions 94
Quick Quiz 96
Key Reactions 97
Problems 97
Looking Ahead 102
Group Learning Activities 104
Putting It Together 104
CHEMICAL CONNECTIONS
3A The Poisonous Puffer Fish 84
3B Octane Rating: What Those Numbers at the Pump Mean 94
04 Alkenes and Alkynes 108
4.1 What Are the Structures and Shapes of Alkenes and Alkynes? 110
4.2 How Do We Name Alkenes and Alkynes? 112
4.3 What Are the Physical Properties of Alkenes and Alkynes? 120
4.4 Why Are 1-Alkynes (Terminal Alkynes) Weak Acids? 122
Summary of Key Questions 123
Quick Quiz 124
Problems 124
Looking Ahead 128
Group Learning Activities 128
CHEMICAL CONNECTIONS
4A Ethylene, a Plant Growth Regulator 109
4B Cis–Trans Isomerism in Vision 111
4C Why Plants Emit Isoprene 121
05 Reactions of Alkenes and Alkynes 129
5.1 What Are the Characteristic Reactions of Alkenes? 130
5.2 What Is a Reaction Mechanism? 130
5.3 What Are the Mechanisms of Electrophilic Additions to Alkenes? 136
5.4 What Are Carbocation Rearrangements? 147
5.5 What Is Hydroboration–Oxidation of an Alkene? 150
5.6 How Can an Alkene Be Reduced to an Alkane? 153
5.7 How Can an Acetylide Anion Be Used to Create a New Carbon–Carbon Bond? 155
5.8 How Can Alkynes Be Reduced to Alkenes and Alkanes? 157
Summary of Key Questions 158
Quick Quiz 159
Key Reactions 160
Problems 161
Looking Ahead 165
Group Learning Activities 166
CHEMICAL CONNECTIONS
5A Catalytic Cracking and the Importance of Alkenes 133
06 Chirality: The Handedness of Molecules 167
6.1 What Are Stereoisomers? 168
6.2 What Are Enantiomers? 169
6.3 How Do We Designate the Configuration of a Stereocenter? 173
6.4 What Is the 2n Rule? 176
6.5 How Do We Describe the Chirality of Cyclic Molecules with Two Stereocenters? 180
6.6 How Do We Describe the Chirality of Molecules with Three or More Stereocenters? 182
6.7 What Are the Properties of Stereoisomers? 183
6.8 How Is Chirality Detected in the Laboratory? 184
6.9 What Is the Significance of Chirality in the Biological World? 185
6.10 How Can Enantiomers Be Resolved? 186
Summary of Key Questions 189
Quick Quiz 190
Problems 191
Chemical Transformations 195
Looking Ahead 196
Group Learning Activities 196
Putting It Together 196
CHEMICAL CONNECTIONS
6A Chiral Drugs 187
07 Haloalkanes 200
7.1 How Are Haloalkanes Named? 201
7.2 What Are the Characteristic Reactions of Haloalkanes? 203
7.3 What Are the Products of Nucleophilic Aliphatic Substitution Reactions? 206
7.4 What Are the SN2 and SN1 Mechanisms for Nucleophilic Substitution? 208
7.5 What Determines Whether SN1 or SN2 Predominates? 211
7.6 How Can SN1 and SN2 Be Predicted Based on Experimental Conditions? 217
7.7 What Are the Products of b-Elimination? 219
7.8 What Are the E1 and E2 Mechanisms for b-Elimination? 222
7.9 When Do Nucleophilic Substitution and b-Elimination Compete? 225
Summary of Key Questions 229
Quick Quiz 230
Key Reactions 231
Problems 231
Chemical Transformations 236
Looking Ahead 237
Group Learning Activities 238
CHEMICAL CONNECTIONS
7A The Environmental Impact of Chlorofluorocarbons 204
7B The Effect of Chlorofluorocarbon Legislation on Asthma Sufferers 228
08 Alcohols, Ethers, and Thiols 239
8.1 What Are Alcohols? 240
8.2 What Are the Characteristic Reactions of Alcohols? 246
8.3 What Are Ethers? 260
8.4 What Are Epoxides? 264
8.5 What Are Thiols? 268
8.6 What Are the Characteristic Reactions of Thiols? 271
Summary of Key Questions 272
Quick Quiz 274
Key Reactions 274
Problems 275
Chemical Transformations 279
Looking Ahead 280
Group Learning Activities 281
CHEMICAL CONNECTIONS
8A Nitroglycerin: An Explosive and a Drug 243
8B Blood Alcohol Screening 260
8C Ethylene Oxide: A Chemical Sterilant 268
09 Benzene and Its Derivatives 282
9.1 What Is the Structure of Benzene? 283
9.2 What Is Aromaticity? 286
9.3 How Are Benzene Compounds Named, and What Are Their Physical Properties? 289
9.4 What Is the Benzylic Position, and How Does It Contribute to Benzene Reactivity? 292
9.5 What Is Electrophilic Aromatic Substitution? 295
9.6 What Is the Mechanism of Electrophilic Aromatic Substitution? 296
9.7 How Do Existing Substituents on Benzene Affect Electrophilic Aromatic Substitution? 305
9.8 What Are Phenols? 314
Summary of Key Questions 321
Quick Quiz 322
Key Reactions 322
Problems 324
Chemical Transformations 329
Looking Ahead 330
Group Learning Activities 330
CHEMICAL CONNECTIONS
9A Carcinogenic Polynuclear Aromatics and Cancer 293
9B Capsaicin, for Those Who Like It Hot 318
10 Amines 331
10.1 What Are Amines? 333
10.2 How Are Amines Named? 334
10.3 What Are the Characteristic Physical Properties of Amines? 337
10.4 What Are the Acid–Base Properties of Amines? 340
10.5 What Are the Reactions of Amines with Acids? 344
10.6 How Are Arylamines Synthesized? 346
10.7 How Do Amines Act as Nucleophiles? 347
Summary of Key Questions 349
Quick Quiz 350
Key Reactions 350
Problems 351
Chemical Transformations 356
Looking Ahead 357
Group Learning Activities 357
Putting It Together 357
CHEMICAL CONNECTIONS
10A Morphine as a Clue in the Design and Discovery of Drugs 332
10B The Poison Dart Frogs of South America: Lethal Amines 338
11 Spectroscopy 361
11.1 What Is Electromagnetic Radiation? 362
11.2 What Is Molecular Spectroscopy? 364
11.3 What Is Infrared Spectroscopy? 364
11.4 How Do We Interpret Infrared Spectra? 367
11.5 What Is Nuclear Magnetic Resonance? 378
11.6 What Is Shielding? 380
11.7 What Is an NMR Spectrum? 380
11.8 How Many Resonance Signals Will a Compound Yield in Its NMR Spectrum? 382
11.9 What Is Signal Integration? 385
11.10 What Is Chemical Shift? 386
11.11 What Is Signal Splitting? 388
11.12 What Is 13C-NMR Spectroscopy, and How Does It Differ from 1H-NMR Spectroscopy? 391
11.13 How Do We Solve an NMR Problem? 394
Summary of Key Questions 398
Quick Quiz 400
Problems 401
Looking Ahead 414
Group Learning Activities 415
CHEMICAL CONNECTIONS
11A Infrared Spectroscopy: A Window on Brain Activity 368
11B Magnetic Resonance Imaging 391
12 Aldehydes and Ketones 416
12.1 What Are Aldehydes and Ketones? 417
12.2 How Are Aldehydes and Ketones Named? 417
12.3 What Are the Physical Properties of Aldehydes and Ketones? 421
12.4 What Is the Most Common Reaction Theme of Aldehydes and Ketones? 422
12.5 What Are Grignard Reagents, and How Do They React with Aldehydes and Ketones? 423
12.6 What Are Hemiacetals and Acetals? 427
12.7 How Do Aldehydes and Ketones React with Ammonia and Amines? 434
12.8 What Is Keto–Enol Tautomerism? 437
12.9 How Are Aldehydes and Ketones Oxidized? 441
12.10 How Are Aldehydes and Ketones Reduced? 443
Summary of Key Questions 445
Quick Quiz 447
Key Reactions 447
Problems 448
Chemical Transformations 454
Spectroscopy 455
Looking Ahead 456
Group Learning Activities 456
CHEMICAL CONNECTIONS
12A A Green Synthesis of Adipic Acid 442
13 Carboxylic Acids 457
13.1 What Are Carboxylic Acids? 458
13.2 How Are Carboxylic Acids Named? 458
13.3 What Are the Physical Properties of Carboxylic Acids? 461
13.4 What Are the Acid–Base Properties of Carboxylic Acids? 462
13.5 How Are Carboxyl Groups Reduced? 466
13.6 What Is Fischer Esterification? 470
13.7 What Are Acid Chlorides? 473
13.8 What Is Decarboxylation? 475
Summary of Key Questions 479
Quick Quiz 480
Key Reactions 480
Problems 481
Chemical Transformations 486
Looking Ahead 487
Group Learning Activities 487
CHEMICAL CONNECTIONS
13A From Willow Bark to Aspirin and Beyond 466
13B Esters as Flavoring Agents 472
13C Ketone Bodies and Diabetes 476
14 Functional Derivatives of Carboxylic Acids 488
14.1 What Are Some Derivatives of Carboxylic Acids, and How Are They Named? 489
14.2 What Are the Characteristic Reactions of Carboxylic Acid Derivatives? 495
14.3 What Is Hydrolysis? 496
14.4 How Do Carboxylic Acid Derivatives React with Alcohols? 501
14.5 How Do Carboxylic Acid Derivatives React with Ammonia and Amines? 503
14.6 How Can Functional Derivatives of Carboxylic Acids Be Interconverted? 505
14.7 How Do Esters React with Grignard Reagents? 507
14.8 How Are Derivatives of Carboxylic Acids Reduced? 509
Summary of Key Questions 513
Quick Quiz 514
Key Reactions 515
Problems 516
Chemical Transformations 522
Looking Ahead 523
Group Learning Activities 523
Putting It Together 523
CHEMICAL CONNECTIONS
14A Ultraviolet Sunscreens and Sunblocks 490
14B From Moldy Clover to a Blood Thinner 491
14C The Penicillins and Cephalosporins: b-Lactam Antibiotics 492
14D The Pyrethrins: Natural Insecticides of Plant Origin 503
14E Systematic Acquired Resistance in Plants 506
15 Enolate Anions 526
15.1 What Are Enolate Anions, and How Are They Formed? 527
15.2 What Is the Aldol Reaction? 530
15.3 What Are the Claisen and Dieckmann Condensations? 537
15.4 How Are Aldol Reactions and Claisen Condensations Involved in Biological Processes? 545
15.5 What Is the Michael Reaction? 547
Summary of Key Questions 554
Quick Quiz 554
Key Reactions 555
Problems 556
Chemical Transformations 561
Looking Ahead 562
Group Learning Activities 563
CHEMICAL CONNECTIONS
15A Drugs That Lower Plasma Levels of Cholesterol 546
15B Antitumor Compounds: The Michael Reaction in Nature 553
16 Organic Polymer Chemistry 564
16.1 What Is the Architecture of Polymers? 565
16.2 How Do We Name and Show the Structure of a Polymer? 565
16.3 What Is Polymer Morphology? Crystalline versus Amorphous Materials 567
16.4 What Is Step-Growth Polymerization? 568
16.5 What Are Chain-Growth Polymers? 573
16.6 What Plastics Are Currently Recycled in Large Quantities? 579
Summary of Key Questions 580
Quick Quiz 581
Key Reactions 582
Problems 582
Looking Ahead 584
Group Learning Activities 585
CHEMICAL CONNECTIONS
16A Stitches That Dissolve 573
16B Paper or Plastic? 575
17 Carbohydrates 586
17.1 What Are Carbohydrates? 586
17.2 What Are Monosaccharides? 587
17.3 What Are the Cyclic Structures of Monosaccharides? 591
17.4 What Are the Characteristic Reactions of Monosaccharides? 596
17.5 What Are Disaccharides and Oligosaccharides? 601
17.6 What Are Polysaccharides? 604
Summary of Key Questions 606
Quick Quiz 608
Key Reactions 608
Problems 609
Looking Ahead 614
Group Learning Activities 614
Putting It Together 615
CHEMICAL CONNECTIONS
17A Relative Sweetness of Carbohydrate and Artificial Sweeteners 602
17B A, B, AB, and O Blood-Group Substances 603
18 Amino Acids and Proteins 619
18.1 What Are the Many Functions of Proteins? 620
18.2 What Are Amino Acids? 620
18.3 What Are the Acid–Base Properties of Amino Acids? 623
18.4 What Are Polypeptides and Proteins? 630
18.5 What Is the Primary Structure of a Polypeptide or Protein? 631
18.6 What Are the Three-Dimensional Shapes of Polypeptides and Proteins? 635
Summary of Key Questions 642
Quick Quiz 643
Key Reactions 644
Problems 645
Looking Ahead 648
Group Learning Activities 648
CHEMICAL CONNECTIONS
18A Spider Silk: A Chemical and Engineering Wonder of Nature 640
19 Lipids 649
19.1 What Are Triglycerides? 650
19.2 What Are Soaps and Detergents? 653
19.3 What Are Phospholipids? 655
19.4 What Are Steroids? 657
19.5 What Are Prostaglandins? 662
19.6 What Are Fat-Soluble Vitamins? 665
Summary of Key Questions 668
Quick Quiz 669
Problems 669
Looking Ahead 672
Group Learning Activities 673
CHEMICAL CONNECTIONS
19A Snake Venom Phospholipases 657
19B Nonsteroidal Estrogen Antagonists 661
20 Nucleic Acids (Online Chapter) 674
20.1 What Are Nucleosides and Nucleotides? 675
20.2 What Is the Structure of DNA? 678
20.3 What Are Ribonucleic Acids (RNA)? 685
20.4 What Is the Genetic Code? 687
20.5 How Is DNA Sequenced? 689
Summary of Key Questions 694
Quick Quiz 696
Problems 696
Group Learning Activities 699
CHEMICAL CONNECTIONS
20A The Search for Antiviral Drugs 677
20B DNA Fingerprinting 694
21 The Organic Chemistry of Metabolism (Online Chapter) 700
21.1 What Are the Key Participants in Glycolysis, the b-Oxidation of Fatty Acids, and the Citric Acid Cycle? 701
21.2 What Is Glycolysis? 706
21.3 What Are the Ten Reactions of Glycolysis? 707
21.4 What Are the Fates of Pyruvate? 711
21.5 What Are the Reactions of the b-Oxidation of Fatty Acids? 713
21.6 What Are the Reactions of the Citric Acid Cycle? 717
Summary of Key Questions 720
Quick Quiz 721
Key Reactions 722
Problems 722
Group Learning Activities 724
Appendix 1 Acid Ionization Constants for the Major Classes of Organic Acids A.1
Appendix 2 Characteristic 1H-NMR Chemical Shifts A.2
Appendix 3 Characteristic 13C-NMR Chemical Shifts A.3
Appendix 4 Characteristic Infrared Absorption Frequencies A.4
Glossary G.1
Answers Section Ans.1
Index I.1
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