DETAILED CONTENTS 2.8 Acid and Base Strength 49 2.9 Predicting Acid-Base Reactions from pK Values 51 2.10 Organic Acids and Organic Bases 53 2 Acids and Bases:The Lewis Definition 56 2.12 Noncovalent Interactions between Molecules 60 Summary 62 Lagniappe-Alkaloids:Naturally Occurring Bases 63 Exercises 64 Organic Compounds:Alkanes and Their Stereochemistry 70 3.1 Functional Groups 70 32 Alkanes and Alkane Isomers 77 33 Alkyl Groups 81 3.4 Naming Alkanes 84 3.5 Properties of alkanes 89 3.6 Conformations of Ethane 3 Conformations of Other Alkanes 92 Summary 97 Lagniappe-Gasoline 9 Exercises99 Organic Compounds:Cycloalkanes and Their Stereochemistry 10s 4.1 Naming Cycloalkanes 106 Cis-Trans Isomerism in Cycloalkanes 109 4.3 Stability of Cycloalkanes:Ring Strain 112 4.4 Conformations of Cycloalkanes 113 4.5 Conformations of Cyclohexane 115 Axial and Equatorial Bonds in Cyclohexane 17 4.7 Conformations of Monosubstituted Cyclohexanes 120 4.8 Conformations of Disubstituted Cyclohexanes 123 4.9 Conformations of Polycyclic Molecules 126 Summary 127 Lagniappe-Molecular Mechanics 128 Exercises 129detailed contents vii 2.8 Acid and Base Strength 49 2.9 Predicting Acid–Base Reactions from pKa Values 51 2.10 Organic Acids and Organic Bases 53 2.11 Acids and Bases: The Lewis Definition 56 2.12 Noncovalent Interactions between Molecules 60 Summary 62 Lagniappe—Alkaloids: Naturally Occurring Bases 63 Exercises 64 Organic Compounds: Alkanes and Their Stereochemistry 70 3.1 Functional Groups 70 3.2 Alkanes and Alkane Isomers 77 3.3 Alkyl Groups 81 3.4 Naming Alkanes 84 3.5 Properties of Alkanes 89 3.6 Conformations of Ethane 90 3.7 Conformations of Other Alkanes 92 Summary 97 Lagniappe—Gasoline 98 Exercises 99 Organic Compounds: Cycloalkanes and Their Stereochemistry 105 4.1 Naming Cycloalkanes 106 4.2 Cis–Trans Isomerism in Cycloalkanes 109 4.3 Stability of Cycloalkanes: Ring Strain 112 4.4 Conformations of Cycloalkanes 113 4.5 Conformations of Cyclohexane 115 4.6 Axial and Equatorial Bonds in Cyclohexane 117 4.7 Conformations of Monosubstituted Cyclohexanes 120 4.8 Conformations of Disubstituted Cyclohexanes 123 4.9 Conformations of Polycyclic Molecules 126 Summary 127 Lagniappe—Molecular Mechanics 128 Exercises 129 3 4 39144_ FM_i-xxiv.indd vii 8/26/09 10:48:49 AM