<ol> Water Solubility and Chemical Bonding, 1 Van der Waals Attraction (Forces), 1 Dipole-Dipole Bonding (Hydrogen Bond), 2 Ionic Attraction, 3 Ion-Dipole Bonding, 4 Alkanes (C<sub>nH<sub>2n 2), 6 Alkenes (C<sub>nH<sub>2 n), 11 Cycloalkanes: Alkene Isomers, 14 Aromatic Hydrocarbons, 16 Halogenated Hydrocarbons, 19 Alcohols, 21 Phenols, 25 Ethers, 30 Aldehydes and Ketones, 33 Amines, 38 Quaternary Ammonium Salts, 46 Carboxylic Acids, 48 Functional Derivatives of Carboxylic Acids, 56 Esters, 56 Amides, 59 Carbonates, Carbamates, and Ureas, 62 Amidines and Guanidines, 64 Sulfonic Acids and Sulfonamides, 66 Sulfonic Acids, 66 Sulfonamides, 66 Thioethers and Nitro Groups, 69 Thioethers, 69 Nitro Groups, 70 Heterocycles, 71 Three-Membered Ring Heterocycles, 71 Four-Membered Ring Heterocycles, 74 Five-Membered Ring Heterocycles, 75 Five-Membered Ring Heterocycles With Two or More Heteroatoms, 80 Six-Membered Ring Heterocycles, 87 Six-Membered Ring Heterocycles With Two Heteroatoms, 88 Saturated Six-Membered Heterocycles, 94 Seven- And Eight-Membered Ring Heterocycles, 94 Bicyclic Heterocycles: Five-Membered Ring Plus Six-Membered Ring, 95 Bicyclic Heterocycles: Six-Membered Ring Plus Six-Membered Ring, 100 Bicyclic Heterocycles: Six-Membered Ring Plus Seven-Membered Ring, 103 Tricyclic Heterocycles, 104 Oligonucleotides and Nucleic Acids, 106 Proteins, 112 Predicting Water Solubility, 122 Empiric Method, 122 Analytic Method, 126 Stereoisomerism-Asymmetric Molecules, 129 Acidity and Basicity, 132 Definitions of Acids and Bases, 132 Relative Strengths of Acids and Bases, 134 Reaction of an Acid With a Base in Water, 136 Acidic and Basic Organic Function Groups, 138 Drug Metabolism, 141 Oxygenase Enzymes, 141 Hydrolase Enzymes, 145 Conjugation Reactions, 145 Index, 149
