CONTENTS Preface xxii About the Author ii 1 INTRODUCTION AND REVIEW 1 1-1 The Origins of Organic Chemistry I 1-2 Principles of Atomie Structure 3 1-3 Bond Formation:The Octet Rule 6 1-4 Lewis Structures 7 1-5 Multiple Bonding 8 Summary:Common Bonding Patterns (Uncharged)9 1-9 Resonance 13 1-10 Structural Formulas 17 1-l1 Molecular Formulas and Empirical Formulas 20 1-12 Arrhenius Acids and Bases 21 1-13 Bronsted-Lowry Acids and Bases 22 4 Lewis Acids and Bases29 Chapter I Glossary 32 Study Problems 34 STRUCTURE AND PROPERTIES 2 OF ORGANIC MOLECULES 40 2-1 Wave Properties of Electrons in Orbitals 40 2-2 Molecular Orbitals 42 2-3 Pi Bonding 45 2.4 Hybridization and Molecular Shapes 46 2-5 Drawing Three-Dimensional Molecules 50 General Rules of Hybridization and Geometry 51 Bond Rotation 55 onds and Mo 212 2.130 2.14 anic Co n74 Chapter 2 Glo Study Problems 79 CONTENTS vi Preface xxii About the Author 111 1 INTRODUCTION AND REVIEW 1 1-1 The Origins of Organic Chemistry 1 1-2 Principles of Atomic Structure 3 1-3 Bond Formation: The Octet Rule 6 1-4 Lewis Structures 7 1-5 Multiple Bonding 8 Summary: Common Bonding Patterns (Uncharged) 9 1-6 Electronegativity and Bond Polarity 9 1-7 Formal Charges 10 1-8 Ionic Structures 12 Summary: Common Bonding Patterns in Organic Compounds and Ions 13 1-9 Resonance 13 1-10 Structural Formulas 17 1-11 Molecular Formulas and Empirical Formulas 20 1-12 Arrhenius Acids and Bases 21 1-13 Bronsted-Lowry Acids and Bases 22 1-14 Lewis Acids and Bases 29 Chapter 1 Glossary 32 Study Problems 34 STRUCTURE AND PROPERTIES 2 OF ORGANIC MOLECULES 40 2-1 Wave Properties of Electrons in Orbitals 40 2-2 Molecular Orbitals 42 2-3 Pi Bonding 45 2-4 Hybridization and Molecular Shapes 46 2-5 Drawing Three-Dimensional Molecules 50 2-6 General Rules of Hybridization and Geometry 51 2-7 Bond Rotation 55 2-8 Isomerism 57 2-9 Polarity of Bonds and Molecules 59 2-10 Intermolecular Forces 62 2-11 Polarity Effects on Solubilities 66 2-12 Hydrocarbons 69 2-13 Organic Compounds Containing Oxygen 72 2-14 Organic Compounds Containing Nitrogen 74 Chapter 2 Glossary 76 Study Problems 79