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Textbook Map: Brown/Poon 5ed.

  • Page ID
    7880
  • 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 Brønsted–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

    Summary of Key Questions 57

    Quick Quiz 58

    Key Reactions 59

    Problems 59

    Looking Ahead 62

    Group Learning Activities 62

    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 104

    Putting It Together 104

    CHEMICAL CONNECTIONS

    3A The Poisonous Puffer Fish 84

    3B Octane Rating: What Those Numbers at the Pump Mean 94

    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

    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

    CHEMICAL CONNECTIONS

    5A Catalytic Cracking and the Importance of Alkenes 133

    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 2nRule? 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

    Summary of Key Questions 189

    Quick Quiz 190

    Problems 191

    Chemical Transformations 195

    Looking Ahead 196

    Group Learning Activities 196

    Putting It Together 196

    CHEMICAL CONNECTIONS

    6A Chiral Drugs 187

    07 Haloalkanes 200

    7.1 How Are Haloalkanes Named? 201

    7.2 What Are the Characteristic Reactions of Haloalkanes? 203

    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

    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

    7A The Environmental Impact of Chlorofluorocarbons 204

    7B The Effect of Chlorofluorocarbon Legislation on Asthma Sufferers 228

    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

    CHEMICAL CONNECTIONS

    8A Nitroglycerin: An Explosive and a Drug 243

    8B Blood Alcohol Screening 260

    8C Ethylene Oxide: A Chemical Sterilant 268

    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 357

    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

    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

    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

    11A Infrared Spectroscopy: A Window on Brain Activity 368

    11B Magnetic Resonance Imaging 391

    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

    12.10 How Are Aldehydes and Ketones Reduced? 443

    Summary of Key Questions 445

    Quick Quiz 447

    Key Reactions 447

    Problems 448

    Chemical Transformations 454

    Spectroscopy 455

    Looking Ahead 456

    Group Learning Activities 456

    CHEMICAL CONNECTIONS

    12A A Green Synthesis of Adipic Acid 442

    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

    13.6 What Is Fischer Esterification? 470

    13.7 What Are Acid Chlorides? 473

    13.8 What Is Decarboxylation? 475

    Summary of Key Questions 479

    Quick Quiz 480

    Key Reactions 480

    Problems 481

    Chemical Transformations 486

    Looking Ahead 487

    Group Learning Activities 487

    CHEMICAL CONNECTIONS

    13A From Willow Bark to Aspirin and Beyond 466

    13B Esters as Flavoring Agents 472

    13C Ketone Bodies and Diabetes 476

    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

    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

    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

    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 CONNECTIONS

    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 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

    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