Brown's Introduction to Organic Chemistry, Global Edition

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.

• 1 Covalent Bonding and Shapes of Molecules 11.1 How Do We Describe the Electronic Structure of Atoms? 21.2 What Is the Lewis Model of Bonding? 51.3 How Do We Predict Bond Angles and the Shapes of Molecules? 131.4 How Do We Predict If a Molecule Is Polar or Nonpolar? 171.5 What Is Resonance? 181.6 What Is the Orbital Overlap Model of Covalent Bonding? 211.7 What Are Functional Groups? 26Summary of Key Questions 31Quick Quiz 32Problems 34Real World Problems 37Looking Ahead 38Group Learning Activities 39Chemical Connections 1A Buckyball: A New Form of Carbon 162 Acids and Bases 402.1 What Are Arrhenius Acids and Bases? 412.2 What Are Brønsted–Lowry Acids and Bases? 422.3 How Do We Measure the Strength of an Acid or Base? 442.4 How Do We Determine the Position of Equilibrium in an Acid–Base Reaction? 462.5 What Are the Relationships between Acidity and Molecular Structure? 482.6 What Are Lewis Acids and Bases? 52Summary of Key Questions 55Quick Quiz 56Key Reactions 57Problems 57Real World Problems 59Looking Ahead 59Group Learning Activities 603 Alkanes and Cycloalkanes 613.1 What Are Alkanes? 623.2 What Is Constitutional Isomerism in Alkanes? 643.3 How Do We Name Alkanes? 663.4 What Are Cycloalkanes? 713.5 How Is the IUPAC System of Nomenclature Applied to Molecules that Contain Functional Groups? 723.6 What Are the Conformations of Alkanes and Cycloalkanes? 733.7 What Is Cis–Trans Isomerism in Cycloalkanes? 803.8 What Are the Physical Properties of Alkanes and Cycloalkanes? 843.9 What Are the Characteristic Reactions of Alkanes? 873.10 What Are the Sources of Alkanes? 88Summary of Key Questions 91Quick Quiz 92Key Reactions 93Problems 93Real World Problems 97Looking Ahead 98Group Learning Activities 99Putting it Together 99Chemical Connections 3A The Poisonous Puffer Fish 813B Octane Rating: What Those Numbers at the Pump Mean 904 Alkenes and Alkynes 1034.1 What Are the Structures and Shapes of Alkenes and Alkynes? 1054.2 How Do We Name Alkenes and Alkynes? 1074.3 What Are the Physical Properties of Alkenes and Alkynes? 1154.4 Why Are 1-Alkynes (Terminal Alkynes) Weak Acids? 116Summary of Key Questions 117Quick Quiz 118Problems 118Real World Problems 121Looking Ahead 122Group Learning Activities 122Chemical Connections 4A Ethylene, a Plant Growth Regulator 1044B Cis–Trans Isomerism in Vision 1064C Why Plants Emit Isoprene 1155 Reactions of Alkenes and Alkynes 1235.1 What Are the Characteristic Reactions of Alkenes? 1235.2 What Is a Reaction Mechanism? 1245.3 What Are the Mechanisms of Electrophilic Additions to Alkenes? 1305.4 What Are Carbocation Rearrangements? 1405.5 What Is Hydroboration–Oxidation of an Alkene? 1435.6 How Can an Alkene Be Reduced to an Alkane? 1455.7 How Can an Acetylide Anion Be Used to Create a New Carbon–Carbon Bond? 1485.8 How Can Alkynes Be Reduced to Alkenes and Alkanes? 150Summary of Key Questions 151Quick Quiz 152Key Reactions 153Problems 154Chemical Transformation 157Real World Problems 158Looking Ahead 158Group Learning Activities 159Chemical Connections 5A Catalytic Cracking and the Importance of Alkenes 1276 Chirality: The Handedness of Molecules 1606.1 What Are Stereoisomers? 1616.2 What Are Enantiomers? 1616.3 How Do We Designate the Configuration of a Stereocenter? 1666.4 What Is the 2n Rule? 1686.5 How Do We Describe the Chirality of Cyclic Molecules with Two Stereocenters? 1726.6 How Do We Describe the Chirality of Molecules with Three or More Stereocenters? 1746.7 What Are the Properties of Stereoisomers? 1746.8 How Is Chirality Detected in the Laboratory? 1756.9 What Is the Significance of Chirality in the Biological World? 1766.10 How Can Enantiomers Be Resolved? 177Summary of Key Questions 179Quick Quiz 180Problems 181Chemical Transformations 184Real World Problems 185Looking Ahead 186Group Learning Activities 187Putting it Together 187Chemical Connections 6A Chiral Drugs 1787 Haloalkanes 1907.1 How Are Haloalkanes Named? 1917.2 What Are the Characteristic Reactions of Haloalkanes? 1937.3 What Are the Products of Nucleophilic Aliphatic Substitution Reactions? 1957.4 What Are the SN2 and SN1 Mechanisms for Nucleophilic Substitution? 1977.5 What Determines Whether SN1 or SN2 Predominates? 2017.6 How Can SN1 and SN2 Be Predicted Based on Experimental Conditions? 2067.7 What Are the Products of β‐Elimination? 2087.8 What Are the E1 and E2 Mechanisms for β‐Elimination? 2117.9 When Do Nucleophilic Substitution and β‐Elimination Compete? 214Summary of Key Questions 217Quick Quiz 218Key Reactions 218Problems 219Chemical Transformations 223Looking Ahead 224Group Learning Activities 225Chemical Connections 7A The Environmental Impact of Chlorofluorocarbons 1937B The Effect of Chlorofluorocarbon Legislation on Asthma Sufferers 2168 Alcohols, Ethers, and Thiols 2268.1 What Are Alcohols? 2278.2 What Are the Characteristic Reactions of Alcohols? 2328.3 What Are Ethers? 2458.4 What Are Epoxides? 2498.5 What Are Thiols? 2538.6 What Are the Characteristic Reactions of Thiols? 256Summary of Key Questions 257Quick Quiz 258Key Reactions 259Problems 260Chemical Transformations 263Real World Problems 264Looking Ahead 264Group Learning Activities 265Chemical Connections 8A Nitroglycerin: An Explosive and a Drug 2308B Blood Alcohol Screening 2458C Ethylene Oxide: A Chemical Sterilant 2539 Benzene and Its Derivatives 2669.1 What Is the Structure of Benzene? 2679.2 What Is Aromaticity? 2709.3 How Are Benzene Compounds Named, and What Are Their Physical Properties? 2739.4 What Is a Benzylic Position, and How Does It Contribute to Benzene Reactivity? 2769.5 What Is Electrophilic Aromatic Substitution? 2789.6 What Is the Mechanism of Electrophilic Aromatic Substitution? 2799.7 How Do Existing Substituents on Benzene Affect Electrophilic Aromatic Substitution? 2889.8 What Are Phenols? 296Summary of Key Questions 303Quick Quiz 304Key Reactions 304Problems 305Chemical Transformations 309Real World Problems 310Looking Ahead 311Group Learning Activities 312Chemical Connections9A Carcinogenic Polynuclear Aromatics and Cancer 2779B Capsaicin, for Those Who Like It Hot 30010 Amines 31310.1 What Are Amines? 31310.2 How Are Amines Named? 31610.3 What Are the Characteristic Physical Properties of Amines? 31910.4 What Are the Acid–Base Properties of Amines? 32110.5 What Are the Reactions of Amines with Acids? 32510.6 How Are Arylamines Synthesized? 32710.7 How Do Amines Act as Nucleophiles? 328Summary of Key Questions 330Quick Quiz 331Key Reactions 331Problems 332Chemical Transformations 334Real World Problems 335Looking Ahead 337Group Learning Activities 337Putting it Together 338Chemical Connections 10A Morphine as a Clue in the Design and Discovery of Drugs 31410B The Poison Dart Frogs of South America: Lethal Amines 31911 Spectroscopy 34111.1 What Is Electromagnetic Radiation? 34211.2 What Is Molecular Spectroscopy? 34411.3 What Is Infrared Spectroscopy? 34411.4 How Do We Interpret Infrared Spectra? 34711.5 What Is Nuclear Magnetic Resonance? 35811.6 What Is Shielding? 36011.7 What Is a 1H-NMR Spectrum? 36011.8 How Many Resonance Signals Will a Compound Yield in Its 1H‐NMR Spectrum? 36211.9 What Is Signal Integration? 36511.10 What Is Chemical Shift? 36611.11 What Is Signal Splitting? 36811.12 What Is 13C‐NMR Spectroscopy, and How Does It Differ from 1H‐NMR Spectroscopy? 37111.13 How Do We Solve an NMR Problem? 374Summary of Key Questions 378Quick Quiz 380Problems 381Real World Problems 393Looking Ahead 394Group Learning Activities 395Chemical Connections 11A Infrared Spectroscopy: A Window on Brain Activity 34811B Infrared Spectroscopy: A Window on Climate Change 35411C Magnetic Resonance Imaging (MRI) 37112 Aldehydes and Ketones 39612.1 What Are Aldehydes and Ketones? 39712.2 How Are Aldehydes and Ketones Named? 39712.3 What Are the Physical Properties of Aldehydes and Ketones? 40112.4 What Is the Most Common Reaction Theme of Aldehydes and Ketones? 40212.5 What Are Grignard Reagents, and How Do They React with Aldehydes and Ketones? 40212.6 What Are Hemiacetals and Acetals? 40712.7 How Do Aldehydes and Ketones React with Ammonia and Amines? 41312.8 What Is Keto‐Enol Tautomerism? 41712.9 How Are Aldehydes and Ketones Oxidized? 42012.10 How Are Aldehydes and Ketones Reduced? 423Summary of Key Questions 425Quick Quiz 426Key Reactions 427Problems 428Chemical Transformations 431Spectroscopy 432Real World Problems 433Looking Ahead 435Group Learning Activities 436Chemical Connections 12A A Green Synthesis of Adipic Acid 42213 Carboxylic Acids 43713.1 What Are Carboxylic Acids? 43713.2 How Are Carboxylic Acids Named? 43813.3 What Are the Physical Properties of Carboxylic Acids? 44113.4 What Are the Acid–Base Properties of Carboxylic Acids? 44213.5 How Are Carboxyl Groups Reduced? 44613.6 What Is Fischer Esterification? 44913.7 What Are Acid Chlorides? 45313.8 What Is Decarboxylation? 455Summary of Key Questions 459Quick Quiz 459Key Reactions 460Problems 461Chemical Transformations 464Real World Problems 464Looking Ahead 467Group Learning Activities 467Chemical Connections 13A From Willow Bark to Aspirin and Beyond 44613B Esters as Flavoring Agents 45113C Ketone Bodies and Diabetes 45614 Functional Derivatives of Carboxylic Acids 46814.1 What Are Some Derivatives of Carboxylic Acids, and How Are They Named? 46914.2 What Are the Characteristic Reactions of Carboxylic Acid Derivatives? 47414.3 What Is Hydrolysis? 47514.4 How Do Carboxylic Acid Derivatives React with Alcohols? 48014.5 How Do Carboxylic Acid Derivatives React with Ammonia and Amines? 48314.6 How Can Functional Derivatives of Carboxylic Acids Be Interconverted? 48514.7 How Do Esters React with Grignard Reagents? 48614.8 How Are Derivatives of Carboxylic Acids Reduced? 488Summary of Key Questions 492Quick Quiz 493Key Reactions 493Problems 495Chemical Transformations 498Real World Problems 498Looking Ahead 501Group Learning Activities 501Putting it Together 501Chemical Connections 14A Ultraviolet Sunscreens and Sunblocks 47014B From Moldy Clover to a Blood Thinner 47114C The Penicillins and Cephalosporins: β‐Lactam Antibiotics 47214D The Pyrethrins: Natural Insecticides of Plant Origin 48214E Systematic Acquired Resistance in Plants 48515 Enolate Anions 50415.1 What Are Enolate Anions, and How Are They Formed? 50515.2 What Is the Aldol Reaction? 50815.3 What Are the Claisen and Dieckmann Condensations? 51515.4 How Are Aldol Reactions and Claisen Condensations Involved in Biological Processes? 52215.5 What Is the Michael Reaction? 524Summary of Key Questions 531Quick Quiz 531Key Reactions 532Problems 533Chemical Transformations 536Real World Problems 537Looking Ahead 540Group Learning Activities 541Chemical Connections 15A Drugs That Lower Plasma Levels of Cholesterol 52315B Antitumor Compounds: The Michael Reaction in Nature 53016 Organic Polymer Chemistry 54216.1 What Is the Architecture of Polymers? 54316.2 How Do We Name and Show the Structure of a Polymer? 54316.3 What Is Polymer Morphology? Crystalline versus Amorphous Materials 54516.4 What Is Step‐Growth Polymerization? 54616.5 What Are Chain‐Growth Polymers? 55116.6 What Plastics Are Currently Recycled in Large Quantities? 557Summary of Key Questions 558Quick Quiz 559Key Reactions 560Problems 560Real World Problem 562Looking Ahead 562Group Learning Activities 562Chemical Connections 16A Stitches That Dissolve 55116B Paper or Plastic? 55317 Carbohydrates 56317.1 What Are Carbohydrates? 56317.2 What Are Monosaccharides? 56417.3 What Are the Cyclic Structures of Monosaccharides? 56817.4 What Are the Characteristic Reactions of Monosaccharides? 57317.5 What Are Disaccharides and Oligosaccharides? 57717.6 What Are Polysaccharides? 581Summary of Key Questions 583Quick Quiz 584Key Reactions 585Problems 586Real World Problems 588Looking Ahead 590Group Learning Activities 591Putting it Together 591Chemical Connections 17A Relative Sweetness of Carbohydrate and Artificial Sweeteners 57817B A, B, AB, and O Blood‐Group Substances 57918 Amino Acids and Proteins 59518.1 What Are the Many Functions of Proteins? 59518.2 What Are Amino Acids? 59618.3 What Are the Acid–Base Properties of Amino Acids? 59918.4 What Are Polypeptides and Proteins? 60618.5 What Is the Primary Structure of a Polypeptide or Protein? 60718.6 What Are the Three‐Dimensional Shapes of Polypeptides and Proteins? 611Summary of Key Questions 618Quick Quiz 619Key Reactions 620Problems 620Real World Problems 622Looking Ahead 623Group Learning Activities 623Chemical Connections 18A Spider Silk: A Chemical and Engineering Wonder of Nature 61619 Lipids (Online Chapter) 62419.1 What Are Triglycerides? 62419.2 What Are Soaps and Detergents? 62819.3 What Are Phospholipids? 63019.4 What Are Steroids? 63219.5 What Are Prostaglandins? 63719.6 What Are Fat‐Soluble Vitamins? 640Summary of Key Questions 643Quick Quiz 644Problems 644Real World Problems 646Looking Ahead 646Group Learning Activities 647Chemical Connections19A Snake Venom Phospholipases 63219B Nonsteroidal Estrogen Antagonists 63620 Nucleic Acids (Online Chapter) 64820.1 What Are Nucleosides and Nucleotides? 64820.2 What Is the Structure of DNA? 65220.3 What Are Ribonucleic Acids (RNA)? 65820.4 What Is the Genetic Code? 66020.5 How Is DNA Sequenced? 662Summary of Key Questions 667Quick Quiz 668Problems 669Real World Problems 671Group Learning Activities 671Chemical Connections20A The Search for Antiviral Drugs 65020B DNA Fingerprinting 66621 The Organic Chemistry of Metabolism (Online Chapter) 67221.1 What Are the Key Participants in Glycolysis, the β‐Oxidation of Fatty Acids, and the Citric Acid Cycle? 67321.2 What Is Glycolysis? 67821.3 What Are the Ten Reactions of Glycolysis? 67821.4 What Are the Fates of Pyruvate? 68321.5 What Are the Reactions of the β‐Oxidation of Fatty Acids? 68521.6 What Are the Reactions of the Citric Acid Cycle? 689Summary of Key Questions 692Quick Quiz 693Key Reactions 693Problems 694Real World Problems 695Group Learning Activities 696Appendix 1 Acid Ionization Constants for the Major Classes of Organic Acids A.1Characteristic 1H‐NMR Chemical Shifts A.1Appendix 2 Characteristic 13C‐NMR Chemical Shifts A.2Characteristic Infrared Absorption Frequencies A.2Glossary G.1Answers Section Ans.1Index I.1