Contents Prologue 1 What Is Organic Chemistry?1 Some Representative Organic Molecules 2 Ginkgolide B-A Complex Organic Compound from the Ginkgo Tree 4 1 Structure and Bonding 6 The Periodic Table 7 订123415 Bonding 70 Lewis Structures 12 1.7 6gO2Mgsr2a 8 Hybridization 32 1.9 Ethane,Ethylene,and Acetylene 36 1.10 Bond Length and Bond Strength 40 1.11 Electronegativity and Bond Polarity 42 1.12 Polarity of Molecules 44 1.13 L-Dopa resentative Organic Molecule 45 Acids and Bases 54 Bronsted-Lowry Acids and Bases 55 2.2 Reactions of Brensted-Lowry Acids and Bases 56 2.3 Acid Strength and pK,58 Predicting the Outcome of Acid-Base Reactions 61 Factors That Determine Acid Strength 62 2.6 Common Acids and Bases 70 Aspirin 71 28 Lewis Acids and Bases 72 ems vi Contents Preface xviii Acknowledgments xxiii List of How To’s xxv List of Mechanisms xxvii List of Selected Applications xxx Prologue 1 What Is Organic Chemistry? 1 Some Representative Organic Molecules 2 Ginkgolide B—A Complex Organic Compound from the Ginkgo Tree 4 1 Structure and Bonding 6 1.1 The Periodic Table 7 1.2 Bonding 10 1.3 Lewis Structures 12 1.4 Lewis Structures Continued 17 1.5 Resonance 18 1.6 Determining Molecular Shape 23 1.7 Drawing Organic Structures 27 1.8 Hybridization 32 1.9 Ethane, Ethylene, and Acetylene 36 1.10 Bond Length and Bond Strength 40 1.11 Electronegativity and Bond Polarity 42 1.12 Polarity of Molecules 44 1.13 L-Dopa—A Representative Organic Molecule 45 Key Concepts 46 Problems 47 2 Acids and Bases 54 2.1 Brønsted–Lowry Acids and Bases 55 2.2 Reactions of Brønsted–Lowry Acids and Bases 56 2.3 Acid Strength and pKa 58 2.4 Predicting the Outcome of Acid–Base Reactions 61 2.5 Factors That Determine Acid Strength 62 2.6 Common Acids and Bases 70 2.7 Aspirin 71 2.8 Lewis Acids and Bases 72 Key Concepts 74 Problems 75 smi75625_fm_00i-xxxiv.indd vi 11/17/09 11:21:09 AM