Contents About the Author ii Preface xxv 1 INTRODUCTION AND REVIEW.1. 2monesA8mescnmegv1 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 10 1-7 Formal Charges 11 1-8 lonic Structures 13 ompoary:Common Bonding Patterns in Organic 111 1.12 Arrhenius Acids and Bas 1-14 EssentialTerms 34 Study Problems 36 STRUCTURE AND PROPERTIES 2 OF ORGANIC MOLECULES 42 2-1 Wave Properties of Electrons in Orbitals 42 2-2 Molecular Orbitals 44 2-3 Pi Bonding 47 Hybridization and Molecular Shapes 48 Rfand Gometry53 Bond Rotation 58 ondsand Molecule 62 6 y :ffe 212 人 213 s72 2-14 Organic Cor Study Problems 83v About the Author iii Preface xxv 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 10 1-7 Formal Charges 11 1-8 Ionic Structures 13 Summary: Common Bonding Patterns in Organic Compounds and Ions 13 1-9 Resonance 14 1-10 Structural Formulas 18 1-11 Molecular Formulas and Empirical Formulas 21 1-12 Arrhenius Acids and Bases 22 1-13 Brønsted–Lowry Acids and Bases 23 1-14 Lewis Acids and Bases 31 Essential Terms 34 Study Problems 36 2 STRUCTURE AND PROPERTIES OF ORGANIC MOLECULES 42 2-1 Wave Properties of Electrons in Orbitals 42 2-2 Molecular Orbitals 44 2-3 Pi Bonding 47 2-4 Hybridization and Molecular Shapes 48 2-5 Drawing Three-Dimensional Molecules 52 2-6 General Rules of Hybridization and Geometry 53 2-7 Bond Rotation 58 2-8 Isomerism 60 2-9 Polarity of Bonds and Molecules 62 2-10 Intermolecular Forces 66 2-11 Polarity Effects on Solubilities 70 2-12 Hydrocarbons 72 2-13 Organic Compounds Containing Oxygen 76 2-14 Organic Compounds Containing Nitrogen 78 Essential Terms 81 Study Problems 83 Contents