1 Covalent Bonding and Shapes of Molecules 1
Summary of Key Questions 31
Quick Quiz 32
Problems 34
Looking Ahead 38
Group Learning Activities 39
2 Acids and Bases 40
Summary of Key Questions 55
Quick Quiz 56
Key Reactions 57
Problems 57
Looking Ahead 59
Group Learning Activities 60
3 Alkanes and Cycloalkanes 61
Summary of Key Questions 91
Quick Quiz 92
Key Reactions 93
Problems 93
Looking Ahead 98
Group Learning Activities 99
Putting it Together 99
4 Alkenes and Alkynes 103
Summary of Key Questions 117
Quick Quiz 118
Problems 118
Looking Ahead 122
Group Learning Activities 122
5 Reactions of Alkenes and Alkynes 123
Summary of Key Questions 151
Quick Quiz 152
Key Reactions 153
Problems 154
Looking Ahead 158
Group Learning Activities 158
6 Chirality: The Handedness of Molecules 160
Summary of Key Questions 179
Quick Quiz 180
Problems 181
Chemical Transformations 185
Looking Ahead 186
Group Learning Activities 186
Putting it Together 187
7 Haloalkanes 190
Summary of Key Questions 217
Quick Quiz 218
Key Reactions 218
Problems 219
Chemical Transformations 223
Looking Ahead 224
Group Learning Activities 225
8 Alcohols, Ethers, and Thiols 226
Summary of Key Questions 257
Quick Quiz 258
Key Reactions 259
Problems 260
Chemical Transformations 264
Looking Ahead 264
Group Learning Activities 265
9 Benzene and Its Derivatives 266
Summary of Key Questions 303
Quick Quiz 304
Key Reactions 304
Problems 305
Chemical Transformations 310
Looking Ahead 311
Group Learning Activities 312
10 Amines 313
Nucleophiles? 328
Summary of Key Questions 330
Quick Quiz 331
Key Reactions 331
Problems 332
Chemical Transformations 337
Looking Ahead 337
Group Learning Activities 338
Putting it Together 338
11 Spectroscopy 341
Summary of Key Questions 378
Quick Quiz 380
Problems 381
Looking Ahead 394
Group Learning Activities 395
12 Aldehydes and Ketones 396
Summary of Key Questions 425
Quick Quiz 426
Key Reactions 427
Problems 428
Chemical Transformations 434
Spectroscopy 435
Looking Ahead 435
Group Learning Activities 436
13 Carboxylic Acids 437
Summary of Key Questions 459
Quick Quiz 459
Key Reactions 460
Problems 461
Chemical Transformations 466
Looking Ahead 466
Group Learning Activities 467
14 Functional Derivatives of Carboxylic Acids 468
Summary of Key Questions 492
Quick Quiz 493
Key Reactions 493
Problems 495
Chemical Transformations 500
Looking Ahead 501
Group Learning Activities 501
Putting it Together 501
15 Enolate Anions 504
Summary of Key Questions 531
Quick Quiz 531
Key Reactions 532
Problems 533
Chemical Transformations 538
Looking Ahead 539
Group Learning Activities 540
16 Organic Polymer Chemistry 542
Summary of Key Questions 558
Quick Quiz 559
Key Reactions 560
Problems 560
Looking Ahead 562
Group Learning Activities 562
17 Carbohydrates 563
Summary of Key Questions 583
Quick Quiz 584
Key Reactions 585
Problems 586
Looking Ahead 589
Group Learning Activities 590
Putting it Together 591
18 Amino Acids and Proteins 595
Summary of Key Questions 618
Quick Quiz 619
Key Reactions 620
Problems 620
Looking Ahead 623
Group Learning Activities 623
19 Lipids (Online Chapter) 624
Summary of Key Questions 643
Quick Quiz 644
Problems 644
Looking Ahead 646
Group Learning Activities 647
20 Nucleic Acids (Online Chapter) 648
Summary of Key Questions 667
Quick Quiz 668
Problems 669
Group Learning Activities 671
21 The Organic Chemistry of Metabolism (Online Chapter) 672
Summary of Key Questions 692
Quick Quiz 693
Key Reactions 693
Problems 694
Group Learning Activities 696
Appendix 1 Acid Ionization Constants for the Major Classes of Organic Acids A.1
Characteristic 1H_NMR Chemical Shifts A.1
Appendix 2 Characteristic 13C_NMR Chemical Shifts A.2
Characteristic Infrared Absorption
Frequencies A.2
Glossary G.1
Answers Section Ans.1
Index I.1
