Introduction to Organic Chemistry

01 Covalent Bonding and Shapes of Molecules 1 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 03 Alkanes and Cycloalkanes 63 Summary of Key Questions 94 Quick Quiz 96 Key Reactions 97 Problems 97 Looking Ahead 102 Group Learning Activities 103 Putting It Together 104 CHEMICAL CONNECTIONS 3A The Poisonous Puffer Fish 84 3B Octane Rating: What Those Numbers at the Pump Mean 94 Summary of Key Questions 57 Quick Quiz 58 Key Reactions 59 Problems 59 Looking Ahead 62 Group Learning Activities 62 04 Alkenes and Alkynes 108 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 5A Catalytic Cracking and the Importance of Alkenes 133 Summary of Key Questions 158 Quick Quiz 159 Key Reactions 160 Problems 161 Looking Ahead 165 Group Learning Activities 166 06 Chirality: The Handedness of Molecules 167 CHEMICAL CONNECTIONS 6A Chiral Drugs 187 Summary of Key Questions 189 Quick Quiz 190 Problems 191 Chemical Transformations 196 Looking Ahead 196 Group Learning Activities 197 Putting It Together 197 CHEMICAL CONNECTIONS 07 Haloalkanes 200 CHEMICAL CONNECTIONS 7A The Environmental Impact of Chlorofluorocarbons 204 7B The Effect of Chlorofluorocarbon Legislation on Asthma Sufferers 228 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 8A Nitroglycerin: An Explosive and a Drug 243 8B Blood Alcohol Screening 260 8C Ethylene Oxide: A Chemical Sterilant 268 08 Alcohols, Ethers, and Thiols 239 Summary of Key Questions 272 Quick Quiz 274 Key Reactions 274 Problems 275 Chemical Transformations 279 Looking Ahead 280 Group Learning Activities 281 09 Benzene and Its Derivatives 282 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 Summary of Key Questions 349 Quick Quiz 350 Key Reactions 350 Problems 351 Chemical Transformations 356 Looking Ahead 356 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 11A Infrared Spectroscopy: A Window on Brain Activity 368 11B Magnetic Resonance Imaging 391 Summary of Key Questions 398 Quick Quiz 400 Problems 401 Looking Ahead 414 Group Learning Activities 415 CHEMICAL CONNECTIONS 12 Aldehydes and Ketones 416 12A A Green Synthesis of Adipic Acid 442 Summary of Key Questions 445 CHEMICAL CONNECTIONS Quick Quiz 447 Key Reactions 447 Problems 448 Chemical Transformations 454 Spectroscopy 455 Looking Ahead 456 Group Learning Activities 456 CHEMICAL CONNECTIONS 13 Carboxylic Acids 457 13A From Willow Bark to Aspirin and Beyond 466 13B Esters as Flavoring Agents 472 13C Ketone Bodies and Diabetes 476 Summary of Key Questions 479 Quick Quiz 480 Key Reactions 480 Problems 481 Chemical Transformations 486 Looking Ahead 487 Group Learning Activities 487 14 Functional Derivatives of Carboxylic Acids 488 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 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 15 Enolate Anions 526 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 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 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 Summary of Key Questions 642 Quick Quiz 643 Key Reactions 644 Problems 645 Looking Ahead 648 Group Learning Activities 648 CHEMICAL CONNECTo IONS 18A Spider Silk: A Chemical and Engineering Wonder of Nature 640 19 Lipids 649 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 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 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 21 The Organic Chemistry of Metabolism (Online Chapter) 700