Introduction to Organic Chemistry (International student edition)

Introduction to Organic Chemistry (International student edition)

By: Thomas Poon (author), William H. Brown (author)Paperback

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This text provides an introduction to organic chemistry for students who require the fundamentals of organic chemistry as a requirement for their major. It is most suited for a one semester organic chemistry course. In an attempt to highlight the relevance of the material to students, the authors place a strong emphasis on showing the interrelationship between organic chemistry and other areas of science, particularly the biological and health sciences. The text illustrates the use of organic chemistry as a tool in these sciences; it also stresses the organic compounds, both natural and synthetic, that surround us in everyday life: in pharmaceuticals, plastics, fibers, agrochemicals, surface coatings, toiletry preparations and cosmetics, food additives, adhesives, and elastomers.

About Author

William H. Brown is Professor Emeritus at Beloit College, where he was twice named Teacher of the Year. He is also the author of two other college textbooks: Organic Chemistry 5/e, coauthored with Chris Foote, Brent Iverson, and Eric Anslyn, published in 2009, and General, Organic, and Biochemistry 9/e, coauthored with Fred Bettelheim, Mary Campbell, and Shawn Farrell, published in 2010. He received his Ph.D. from Columbia University under the direction of Gilbert Stork and did postdoctoral work at California Institute of Technology and the University of Arizona. Twice he was Director of a Beloit College World Affairs Center seminar at the University of Glasgow, Scotland. In 1999, he retired from Beloit College to devote more time to writing and development of educational materials. Although officially retired, he continues to teach Special Topics in Organic Synthesis on a yearly basis. Bill and his wife Carolyn enjoy hiking in the canyon country of the Southwest. In addition, they both enjoy quilting and quilts. Thomas Poon is Associate Professor of Chemistry in the Joint Science Department of Claremont McKenna, Pitzer, and Scripps Colleges, three of the five undergraduate institutions that make up the Claremont Colleges in Claremont, California. He received his B.S. degree from Fairfield University (CT) and his Ph.D. from the University of California, Los Angeles under the direction of Christopher S. Foote. Poon was a Camille and Henry Dreyfus Postdoctoral Fellow under Bradford P. Mundy at Colby College (ME) before joining the faculty at Randolph-Macon College (VA) where he received the Thomas Branch Award for Excellence in Teaching in 1999. He was a visiting scholar at Columbia University (NY) in 2002 (and again in 2004) where he worked on projects in both research and education with his friend and mentor, Nicholas J. Turro. He has taught organic chemistry, forensic chemistry, upper-level courses in advanced laboratory techniques, and a first-year seminar class titled Science of Identity. His favorite activity is working alongside undergraduates in the laboratory on research problems involving the investigation of synthetic methodology in zeolites, zeolite photochemistry, natural products isolation, and reactions of singlet oxygen. When not in the lab, he likes to play guitar and sing funny chemistry songs to his daughter Sophie.


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 Bronsted 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 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 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 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 5A Catalytic Cracking and the Importance of Alkenes 133 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 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 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 7.1 How Are Haloalkanes Named? 201 7.2 What Are the Characteristic Reactions of Haloalkanes? 203 CHEMICAL CONNECTIONS 7A The Environmental Impact of Chlorofluorocarbons 204 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 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 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 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 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 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 11A Infrared Spectroscopy: A Window on Brain Activity 368 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 11B Magnetic Resonance Imaging 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 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 12A A Green Synthesis of Adipic Acid 442 12.10 How Are Aldehydes and Ketones Reduced? 443 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 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 13A From Willow Bark to Aspirin and Beyond 466 13.6 What Is Fischer Esterification? 470 13B Esters as Flavoring Agents 472 13.7 What Are Acid Chlorides? 473 13.8 What Is Decarboxylation? 475 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 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 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 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 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 CONNECTo IONS 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 21.5 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 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

Product Details

  • ISBN13: 9781118321768
  • Format: Paperback
  • Number Of Pages: 792
  • ID: 9781118321768
  • weight: 1558
  • ISBN10: 1118321766
  • edition: International student edition

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