Brown, William H., Jr. (Beloit College), Thomas Poon (Claremont, McKenna, Pitzer, & Scripps College)

Brown's Introduction to Organic Chemistry, Global Edition

• Broschiertes Buch

Produktbeschreibung

Brown's Introduction to Organic Chemistry 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.

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Produktdetails

• Verlag: John Wiley & Sons Inc
• 6 ed
• Seitenzahl: 720
• Erscheinungstermin: 14. Juli 2017
• Englisch
• Abmessung: 223mm x 281mm x 39mm
• Gewicht: 2022g
• ISBN-13: 9781119382881
• ISBN-10: 1119382882
• Artikelnr.: 54588397

Autorenporträt

William H. Brown is Professor Emeritus at Beloit College, where he was twice named Teacher of the Year. He received his PhD from Columbia University under the direction of Gilbert Stork and did post--doctoral 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.

Inhaltsangabe

1 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? 13 1.4 How Do We Predict If a Molecule Is Polar or Nonpolar? 17 1.5 What Is Resonance? 18 1.6 What Is the Orbital Overlap Model of Covalent Bonding? 21 1.7 What Are Functional Groups? 26 Summary of Key Questions 31 Quick Quiz 32 Problems 34 Real World Problems 37 Looking Ahead 38 Group Learning Activities 39 Chemical Connections 1A Buckyball: A New Form of Carbon 16 2 Acids and Bases 40 2.1 What Are Arrhenius Acids and Bases? 41 2.2 What Are Brønsted-Lowry Acids and Bases? 42 2.3 How Do We Measure the Strength of an Acid or Base? 44 2.4 How Do We Determine the Position of Equilibrium in an Acid-Base Reaction? 46 2.5 What Are the Relationships between Acidity and Molecular Structure? 48 2.6 What Are Lewis Acids and Bases? 52 Summary of Key Questions 55 Quick Quiz 56 Key Reactions 57 Problems 57 Real World Problems 59 Looking Ahead 59 Group Learning Activities 60 3 Alkanes and Cycloalkanes 61 3.1 What Are Alkanes? 62 3.2 What Is Constitutional Isomerism in Alkanes? 64 3.3 How Do We Name Alkanes? 66 3.4 What Are Cycloalkanes? 71 3.5 How Is the IUPAC System of Nomenclature Applied to Molecules that Contain Functional Groups? 72 3.6 What Are the Conformations of Alkanes and Cycloalkanes? 73 3.7 What Is Cis-Trans Isomerism in Cycloalkanes? 80 3.8 What Are the Physical Properties of Alkanes and Cycloalkanes? 84 3.9 What Are the Characteristic Reactions of Alkanes? 87 3.10 What Are the Sources of Alkanes? 88 Summary of Key Questions 91 Quick Quiz 92 Key Reactions 93 Problems 93 Real World Problems 97 Looking Ahead 98 Group Learning Activities 99 Putting it Together 99 Chemical Connections 3A The Poisonous Puffer Fish 81 3B Octane Rating: What Those Numbers at the Pump Mean 90 4 Alkenes and Alkynes 103 4.1 What Are the Structures and Shapes of Alkenes and Alkynes? 105 4.2 How Do We Name Alkenes and Alkynes? 107 4.3 What Are the Physical Properties of Alkenes and Alkynes? 115 4.4 Why Are 1-Alkynes (Terminal Alkynes) Weak Acids? 116 Summary of Key Questions 117 Quick Quiz 118 Problems 118 Real World Problems 121 Looking Ahead 122 Group Learning Activities 122 Chemical Connections 4A Ethylene, a Plant Growth Regulator 104 4B Cis-Trans Isomerism in Vision 106 4C Why Plants Emit Isoprene 115 5 Reactions of Alkenes and Alkynes 123 5.1 What Are the Characteristic Reactions of Alkenes? 123 5.2 What Is a Reaction Mechanism? 124 5.3 What Are the Mechanisms of Electrophilic Additions to Alkenes? 130 5.4 What Are Carbocation Rearrangements? 140 5.5 What Is Hydroboration-Oxidation of an Alkene? 143 5.6 How Can an Alkene Be Reduced to an Alkane? 145 5.7 How Can an Acetylide Anion Be Used to Create a New Carbon-Carbon Bond? 148 5.8 How Can Alkynes Be Reduced to Alkenes and Alkanes? 150 Summary of Key Questions 151 Quick Quiz 152 Key Reactions 153 Problems 154 Chemical Transformation 157 Real World Problems 158 Looking Ahead 158 Group Learning Activities 159 Chemical Connections 5A Catalytic Cracking and the Importance of Alkenes 127 6 Chirality: The Handedness of Molecules 160 6.1 What Are Stereoisomers? 161 6.2 What Are Enantiomers? 161 6.3 How Do We Designate the Configuration of a Stereocenter? 166 6.4 What Is the 2n Rule? 168 6.5 How Do We Describe the Chirality of Cyclic Molecules with Two Stereocenters? 172 6.6 How Do We Describe the Chirality of Molecules with Three or More Stereocenters? 174 6.7 What Are the Properties of Stereoisomers? 174 6.8 How Is Chirality Detected in the Laboratory? 175 6.9 What Is the Significance of Chirality in the Biological World? 176 6.10 How Can Enantiomers Be Resolved? 177 Summary of Key Questions 179 Quick Quiz 180 Problems 181 Chemical Transformations 184 Real World Problems 185 Looking Ahead 186 Group Learning Activities 187 Putting it Together 187 Chemical Connections 6A Chiral Drugs 178 7 Haloalkanes 190 7.1 How Are Haloalkanes Named? 191 7.2 What Are the Characteristic Reactions of Haloalkanes? 193 7.3 What Are the Products of Nucleophilic Aliphatic Substitution Reactions? 195 7.4 What Are the SN2 and SN1 Mechanisms for Nucleophilic Substitution? 197 7.5 What Determines Whether SN1 or SN2 Predominates? 201 7.6 How Can SN1 and SN2 Be Predicted Based on Experimental Conditions? 206 7.7 What Are the Products of ß
Elimination? 208 7.8 What Are the E1 and E2 Mechanisms for ß
Elimination? 211 7.9 When Do Nucleophilic Substitution and ß
Elimination Compete? 214 Summary of Key Questions 217 Quick Quiz 218 Key Reactions 218 Problems 219 Chemical Transformations 223 Looking Ahead 224 Group Learning Activities 225 Chemical Connections 7A The Environmental Impact of Chlorofluorocarbons 193 7B The Effect of Chlorofluorocarbon Legislation on Asthma Sufferers 216 8 Alcohols, Ethers, and Thiols 226 8.1 What Are Alcohols? 227 8.2 What Are the Characteristic Reactions of Alcohols? 232 8.3 What Are Ethers? 245 8.4 What Are Epoxides? 249 8.5 What Are Thiols? 253 8.6 What Are the Characteristic Reactions of Thiols? 256 Summary of Key Questions 257 Quick Quiz 258 Key Reactions 259 Problems 260 Chemical Transformations 263 Real World Problems 264 Looking Ahead 264 Group Learning Activities 265 Chemical Connections 8A Nitroglycerin: An Explosive and a Drug 230 8B Blood Alcohol Screening 245 8C Ethylene Oxide: A Chemical Sterilant 253 9 Benzene and Its Derivatives 266 9.1 What Is the Structure of Benzene? 267 9.2 What Is Aromaticity? 270 9.3 How Are Benzene Compounds Named, and What Are Their Physical Properties? 273 9.4 What Is a Benzylic Position, and How Does It Contribute to Benzene Reactivity? 276 9.5 What Is Electrophilic Aromatic Substitution? 278 9.6 What Is the Mechanism of Electrophilic Aromatic Substitution? 279 9.7 How Do Existing Substituents on Benzene Affect Electrophilic Aromatic Substitution? 288 9.8 What Are Phenols? 296 Summary of Key Questions 303 Quick Quiz 304 Key Reactions 304 Problems 305 Chemical Transformations 309 Real World Problems 310 Looking Ahead 311 Group Learning Activities 312 Chemical Connections 9A Carcinogenic Polynuclear Aromatics and Cancer 277 9B Capsaicin, for Those Who Like It Hot 300 10 Amines 313 10.1 What Are Amines? 313 10.2 How Are Amines Named? 316 10.3 What Are the Characteristic Physical Properties of Amines? 319 10.4 What Are the Acid-Base Properties of Amines? 321 10.5 What Are the Reactions of Amines with Acids? 325 10.6 How Are Arylamines Synthesized? 327 10.7 How Do Amines Act as Nucleophiles? 328 Summary of Key Questions 330 Quick Quiz 331 Key Reactions 331 Problems 332 Chemical Transformations 334 Real World Problems 335 Looking Ahead 337 Group Learning Activities 337 Putting it Together 338 Chemical Connections 10A Morphine as a Clue in the Design and Discovery of Drugs 314 10B The Poison Dart Frogs of South America: Lethal Amines 319 11 Spectroscopy 341 11.1 What Is Electromagnetic Radiation? 342 11.2 What Is Molecular Spectroscopy? 344 11.3 What Is Infrared Spectroscopy? 344 11.4 How Do We Interpret Infrared Spectra? 347 11.5 What Is Nuclear Magnetic Resonance? 358 11.6 What Is Shielding? 360 11.7 What Is a 1H-NMR Spectrum? 360 11.8 How Many Resonance Signals Will a Compound Yield in Its 1H
NMR Spectrum? 362 11.9 What Is Signal Integration? 365 11.10 What Is Chemical Shift? 366 11.11 What Is Signal Splitting? 368 11.12 What Is 13C
NMR Spectroscopy, and How Does It Differ from 1H
NMR Spectroscopy? 371 11.13 How Do We Solve an NMR Problem? 374 Summary of Key Questions 378 Quick Quiz 380 Problems 381 Real World Problems 393 Looking Ahead 394 Group Learning Activities 395 Chemical Connections 11A Infrared Spectroscopy: A Window on Brain Activity 348 11B Infrared Spectroscopy: A Window on Climate Change 354 11C Magnetic Resonance Imaging (MRI) 371 12 Aldehydes and Ketones 396 12.1 What Are Aldehydes and Ketones? 397 12.2 How Are Aldehydes and Ketones Named? 397 12.3 What Are the Physical Properties of Aldehydes and Ketones? 401 12.4 What Is the Most Common Reaction Theme of Aldehydes and Ketones? 402 12.5 What Are Grignard Reagents, and How Do They React with Aldehydes and Ketones? 402 12.6 What Are Hemiacetals and Acetals? 407 12.7 How Do Aldehydes and Ketones React with Ammonia and Amines? 413 12.8 What Is KetöEnol Tautomerism? 417 12.9 How Are Aldehydes and Ketones Oxidized? 420 12.10 How Are Aldehydes and Ketones Reduced? 423 Summary of Key Questions 425 Quick Quiz 426 Key Reactions 427 Problems 428 Chemical Transformations 431 Spectroscopy 432 Real World Problems 433 Looking Ahead 435 Group Learning Activities 436 Chemical Connections 12A A Green Synthesis of Adipic Acid 422 13 Carboxylic Acids 437 13.1 What Are Carboxylic Acids? 437 13.2 How Are Carboxylic Acids Named? 438 13.3 What Are the Physical Properties of Carboxylic Acids? 441 13.4 What Are the Acid-Base Properties of Carboxylic Acids? 442 13.5 How Are Carboxyl Groups Reduced? 446 13.6 What Is Fischer Esterification? 449 13.7 What Are Acid Chlorides? 453 13.8 What Is Decarboxylation? 455 Summary of Key Questions 459 Quick Quiz 459 Key Reactions 460 Problems 461 Chemical Transformations 464 Real World Problems 464 Looking Ahead 467 Group Learning Activities 467 Chemical Connections 13A From Willow Bark to Aspirin and Beyond 446 13B Esters as Flavoring Agents 451 13C Ketone Bodies and Diabetes 456 14 Functional Derivatives of Carboxylic Acids 468 14.1 What Are Some Derivatives of Carboxylic Acids, and How Are They Named? 469 14.2 What Are the Characteristic Reactions of Carboxylic Acid Derivatives? 474 14.3 What Is Hydrolysis? 475 14.4 How Do Carboxylic Acid Derivatives React with Alcohols? 480 14.5 How Do Carboxylic Acid Derivatives React with Ammonia and Amines? 483 14.6 How Can Functional Derivatives of Carboxylic Acids Be Interconverted? 485 14.7 How Do Esters React with Grignard Reagents? 486 14.8 How Are Derivatives of Carboxylic Acids Reduced? 488 Summary of Key Questions 492 Quick Quiz 493 Key Reactions 493 Problems 495 Chemical Transformations 498 Real World Problems 498 Looking Ahead 501 Group Learning Activities 501 Putting it Together 501 Chemical Connections 14A Ultraviolet Sunscreens and Sunblocks 470 14B From Moldy Clover to a Blood Thinner 471 14C The Penicillins and Cephalosporins: ß
Lactam Antibiotics 472 14D The Pyrethrins: Natural Insecticides of Plant Origin 482 14E Systematic Acquired Resistance in Plants 485 15 Enolate Anions 504 15.1 What Are Enolate Anions, and How Are They Formed? 505 15.2 What Is the Aldol Reaction? 508 15.3 What Are the Claisen and Dieckmann Condensations? 515 15.4 How Are Aldol Reactions and Claisen Condensations Involved in Biological Processes? 522 15.5 What Is the Michael Reaction? 524 Summary of Key Questions 531 Quick Quiz 531 Key Reactions 532 Problems 533 Chemical Transformations 536 Real World Problems 537 Looking Ahead 540 Group Learning Activities 541 Chemical Connections 15A Drugs That Lower Plasma Levels of Cholesterol 523 15B Antitumor Compounds: The Michael Reaction in Nature 530 16 Organic Polymer Chemistry 542 16.1 What Is the Architecture of Polymers? 543 16.2 How Do We Name and Show the Structure of a Polymer? 543 16.3 What Is Polymer Morphology? Crystalline versus Amorphous Materials 545 16.4 What Is Step
Growth Polymerization? 546 16.5 What Are Chain
Growth Polymers? 551 16.6 What Plastics Are Currently Recycled in Large Quantities? 557 Summary of Key Questions 558 Quick Quiz 559 Key Reactions 560 Problems 560 Real World Problem 562 Looking Ahead 562 Group Learning Activities 562 Chemical Connections 16A Stitches That Dissolve 551 16B Paper or Plastic? 553 17 Carbohydrates 563 17.1 What Are Carbohydrates? 563 17.2 What Are Monosaccharides? 564 17.3 What Are the Cyclic Structures of Monosaccharides? 568 17.4 What Are the Characteristic Reactions of Monosaccharides? 573 17.5 What Are Disaccharides and Oligosaccharides? 577 17.6 What Are Polysaccharides? 581 Summary of Key Questions 583 Quick Quiz 584 Key Reactions 585 Problems 586 Real World Problems 588 Looking Ahead 590 Group Learning Activities 591 Putting it Together 591 Chemical Connections 17A Relative Sweetness of Carbohydrate and Artificial Sweeteners 578 17B A, B, AB, and O Blood
Group Substances 579 18 Amino Acids and Proteins 595 18.1 What Are the Many Functions of Proteins? 595 18.2 What Are Amino Acids? 596 18.3 What Are the Acid-Base Properties of Amino Acids? 599 18.4 What Are Polypeptides and Proteins? 606 18.5 What Is the Primary Structure of a Polypeptide or Protein? 607 18.6 What Are the Three
Dimensional Shapes of Polypeptides and Proteins? 611 Summary of Key Questions 618 Quick Quiz 619 Key Reactions 620 Problems 620 Real World Problems 622 Looking Ahead 623 Group Learning Activities 623 Chemical Connections 18A Spider Silk: A Chemical and Engineering Wonder of Nature 616 19 Lipids (Online Chapter) 624 19.1 What Are Triglycerides? 624 19.2 What Are Soaps and Detergents? 628 19.3 What Are Phospholipids? 630 19.4 What Are Steroids? 632 19.5 What Are Prostaglandins? 637 19.6 What Are Fat
Soluble Vitamins? 640 Summary of Key Questions 643 Quick Quiz 644 Problems 644 Real World Problems 646 Looking Ahead 646 Group Learning Activities 647 Chemical Connections 19A Snake Venom Phospholipases 632 19B Nonsteroidal Estrogen Antagonists 636 20 Nucleic Acids (Online Chapter) 648 20.1 What Are Nucleosides and Nucleotides? 648 20.2 What Is the Structure of DNA? 652 20.3 What Are Ribonucleic Acids (RNA)? 658 20.4 What Is the Genetic Code? 660 20.5 How Is DNA Sequenced? 662 Summary of Key Questions 667 Quick Quiz 668 Problems 669 Real World Problems 671 Group Learning Activities 671 Chemical Connections 20A The Search for Antiviral Drugs 650 20B DNA Fingerprinting 666 21 The Organic Chemistry of Metabolism (Online Chapter) 672 21.1 What Are the Key Participants in Glycolysis, the ß
Oxidation of Fatty Acids, and the Citric Acid Cycle? 673 21.2 What Is Glycolysis? 678 21.3 What Are the Ten Reactions of Glycolysis? 678 21.4 What Are the Fates of Pyruvate? 683 21.5 What Are the Reactions of the ß
Oxidation of Fatty Acids? 685 21.6 What Are the Reactions of the Citric Acid Cycle? 689 Summary of Key Questions 692 Quick Quiz 693 Key Reactions 693 Problems 694 Real World Problems 695 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