| Preface |
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xvii | |
| To the Student |
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1 | (5) |
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6 | (35) |
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How Electrons Are Arranged in Atoms |
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7 | (1) |
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Ionic and Covalent Bonding |
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8 | (4) |
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9 | (1) |
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10 | (2) |
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Carbon and the Covalent Bond |
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12 | (1) |
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Carbon-Carbon Single Bonds |
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13 | (1) |
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14 | (1) |
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15 | (2) |
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17 | (1) |
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18 | (1) |
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Writing Structural Formulas |
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19 | (2) |
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Abbreviated Structural Formulas |
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21 | (2) |
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23 | (1) |
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24 | (2) |
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26 | (1) |
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The Orbital View of Bonding; the Sigma Bond |
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27 | (1) |
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Carbon sp3 Hybrid Orbitals |
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28 | (2) |
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Tetrahedral Carbon; the Bonding in Methane |
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30 | (2) |
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Classification According to Molecular Framework |
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32 | (3) |
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32 | (1) |
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33 | (1) |
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33 | (2) |
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Classification According to Functional Group |
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35 | (6) |
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37 | (4) |
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Alkanes and Cycloalkanes; Conformational and Geometric Isomerism |
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41 | (32) |
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The Structures of Alkanes |
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42 | (1) |
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Nomenclature of Organic Compounds |
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43 | (1) |
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IUPAC Rules for Naming Alkanes |
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44 | (2) |
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Alkyl and Halogen Substituents |
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46 | (2) |
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48 | (1) |
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A Closer Look at Natural Gas |
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49 | (1) |
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49 | (1) |
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Physical Properties of Alkanes and Nonbonding Intermolecular Interactions |
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50 | (2) |
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A Closer Look at Hydrogen Bonding |
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51 | (1) |
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52 | (2) |
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Cycloalkane Nomenclature and Conformation |
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54 | (5) |
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Cis-Trans Isomerism in Cycloalkanes |
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59 | (2) |
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A Word About Isomers--Possible and Impossible |
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60 | (1) |
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61 | (1) |
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62 | (4) |
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Oxidation and Combustion; Alkanes as Fuels |
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62 | (2) |
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64 | (1) |
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A Word About Methane, Marsh Gas, and Miller's Experiment |
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65 | (1) |
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The Free-Radical Chain Mechanism of Halogenation |
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66 | (7) |
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68 | (1) |
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68 | (1) |
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68 | (5) |
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73 | (46) |
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Definition and Classification |
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74 | (1) |
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75 | (3) |
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Some Facts About Double Bonds |
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78 | (1) |
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The Orbital Model of a Double Bond; the Pi Bond |
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79 | (2) |
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Cis-Trans Isomerism in Alkenes |
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81 | (3) |
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A Word About The Chemistry of Vision |
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82 | (2) |
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Addition and Substitution Reactions Compared |
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84 | (1) |
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84 | (2) |
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84 | (1) |
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Addition of Water (Hydration) |
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85 | (1) |
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86 | (1) |
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Addition of Unsymmetric Reagents to Unsymmetric Alkenes; Markovnikov's Rule |
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86 | (2) |
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Mechanism of Electrophilic Addition to Alkenes |
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88 | (2) |
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Markovnikov's Rule Explained |
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90 | (2) |
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Reaction Equilibrium: What Makes a Reaction Go? |
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92 | (1) |
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Reaction Rates: How Fast Does a Reaction Go? |
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93 | (3) |
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96 | (1) |
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97 | (1) |
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Additions to Conjugated Systems |
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98 | (3) |
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Electrophilic Additions to Conjugated Dienes |
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98 | (2) |
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Cycloaddition to Conjugated Dienes: The Diels--Alder Reaction |
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100 | (1) |
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Free-Radical Additions; Polyethylene |
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101 | (1) |
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102 | (4) |
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Oxidation with Permanganate; a Chemical Test |
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103 | (1) |
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103 | (1) |
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A Word About Ethylene: Raw Material and Plant Hormone |
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104 | (1) |
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105 | (1) |
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Some Facts About Triple Bonds |
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106 | (1) |
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The Orbital Model of a Triple Bond |
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106 | (1) |
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Addition Reactions of Alkynes |
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107 | (3) |
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A Word About Petroleum, Gasoline, and Octane Number |
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108 | (2) |
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110 | (9) |
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A Closer Look at Petroleum |
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111 | (1) |
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112 | (1) |
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113 | (1) |
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114 | (5) |
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119 | (30) |
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120 | (1) |
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The Kekule Structure of Benzene |
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121 | (1) |
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Resonance Model for Benzene |
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122 | (1) |
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Orbital Model for Benzene |
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122 | (1) |
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123 | (1) |
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Nomenclature of Aromatic Compounds |
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123 | (3) |
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The Resonance Energy of Benzene |
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126 | (1) |
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Electrophilic Aromatic Substitution |
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127 | (1) |
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The Mechanism of Electrophilic Aromatic Substitution |
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128 | (4) |
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130 | (1) |
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130 | (1) |
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131 | (1) |
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131 | (1) |
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Ring-Activating and Ring-Deactivating Substituents |
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132 | (1) |
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Ortho, Para-Directing and Meta-Directing Groups |
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133 | (5) |
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Ortho, Para-Directing Groups |
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134 | (2) |
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136 | (2) |
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Substituent Effects on Reactivity |
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138 | (1) |
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The Importance of Directing Effects in Synthesis |
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138 | (1) |
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Polycyclic Aromatic Hydrocarbons |
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139 | (10) |
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A Word About Polycyclic Aromatic Hydrocarbons and Cancer |
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140 | (1) |
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A Closer Look at Polycyclic Aromatic Hydrocarbons |
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141 | (1) |
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A Word About C60, an Aromatic Sphere: The Fullerenes |
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142 | (2) |
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144 | (1) |
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145 | (1) |
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145 | (4) |
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149 | (33) |
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Chirality and Enantiomers |
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150 | (1) |
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Stereogenic Centers; the Stereogenic Carbon Atom |
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151 | (4) |
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Configuration and the R-S Convention |
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155 | (4) |
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The E-Z Convention for Cis-Trans Isomers |
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159 | (1) |
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Polarized Light and Optical Activity |
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160 | (4) |
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A Word About Pasteur's Experiments and the van't Hoff-LeBel Explanation |
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162 | (2) |
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Properties of Enantiomers |
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164 | (1) |
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Fischer Projection Formulas |
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165 | (2) |
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Compounds with More Than One Stereogenic Center; Diastereomers |
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167 | (2) |
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Meso Compounds; the Stereoisomers of Tartaric Acid |
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169 | (2) |
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Stereochemistry: A Recap of Definitions |
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171 | (1) |
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Stereochemistry and Chemical Reactions |
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172 | (3) |
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A Word About Enantiomers and Biological Activity |
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174 | (1) |
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Resolution of a Racemic Mixture |
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175 | (7) |
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A Closer Look at Thalidomide |
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176 | (1) |
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177 | (5) |
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Organic Halogen Compounds; Substitution and Elimination Reactions |
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182 | (25) |
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Nucleophilic Substitution |
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183 | (1) |
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Examples of Nucleophilic Substitutions |
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183 | (4) |
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Nucleophilic Substitution Mechanisms |
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187 | (1) |
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188 | (2) |
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190 | (3) |
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The SN1 and SN2 Mechanisms Compared |
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193 | (2) |
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A Word About SN2 Reactions in Nature: Biological Methylations |
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194 | (1) |
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Dehydrohalogenation, an Elimination Reaction; the E2 and E1 Mechanisms |
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195 | (2) |
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Substitution and Elimination in Competition |
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197 | (2) |
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197 | (1) |
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197 | (1) |
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198 | (1) |
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Polyhalogenated Aliphatic Compounds |
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199 | (8) |
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A Word About CFCs, the Ozone Layer, and Trade-Offs |
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200 | (2) |
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A Word About Halogenated Organic Compounds from the Sea |
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202 | (1) |
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203 | (1) |
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203 | (1) |
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204 | (3) |
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Alcohols, Phenols, and Thiols |
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207 | (27) |
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208 | (2) |
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A Word About Industrial Alcohols |
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209 | (1) |
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Classification of Alcohols |
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210 | (1) |
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210 | (1) |
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Hydrogen Bonding in Alcohols and Phenols |
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211 | (1) |
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Acidity and Basicity Reviewed |
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212 | (2) |
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The Acidity of Alcohols and Phenols |
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214 | (3) |
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The Basicity of Alcohols and Phenols |
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217 | (1) |
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Dehydration of Alcohols to Alkenes |
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217 | (2) |
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The Reaction of Alcohols with Hydrogen Halides |
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219 | (1) |
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Other Ways to Prepare Alkyl Halides from Alcohols |
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220 | (1) |
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A Comparison of Alcohols and Phenols |
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221 | (1) |
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Oxidation of Alcohols to Aldehydes, Ketones, and Carboxylic Acids |
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221 | (3) |
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A Word About Biologically Important Alcohols and Phenols |
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223 | (1) |
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Alcohols with More Than One Hydroxyl Group |
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224 | (1) |
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Aromatic Substitution in Phenols |
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225 | (2) |
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A Word About Quinones and the Bombardier Beetle |
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226 | (1) |
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227 | (1) |
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227 | (1) |
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Thiols, the Sulfur Analogs of Alcohols and Phenols |
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228 | (6) |
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A Word About Hair---Curly or Straight |
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229 | (1) |
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230 | (1) |
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231 | (3) |
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234 | (19) |
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235 | (1) |
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Physical Properties of Ethers |
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236 | (1) |
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237 | (1) |
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The Grignard Reagent; an Organometallic Compound |
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237 | (3) |
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240 | (2) |
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241 | (1) |
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242 | (2) |
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A Word About Ether and Anesthesia |
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243 | (1) |
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244 | (2) |
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A Word About The Gypsy Moth's Epoxide |
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245 | (1) |
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246 | (1) |
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247 | (6) |
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249 | (1) |
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250 | (3) |
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253 | (32) |
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Nomenclature of Aldehydes and Ketones |
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254 | (1) |
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Some Common Aldehydes and Ketones |
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255 | (2) |
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Synthesis of Aldehydes and Ketones |
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257 | (1) |
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Aldehydes and Ketones in Nature |
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258 | (1) |
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259 | (1) |
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Nucleophilic Addition to Carbonyl Groups: An Overview |
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260 | (1) |
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Addition of Alcohols: Formation of Hemiacetals and Acetals |
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261 | (4) |
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Addition of Water; Hydration of Aldehydes and Ketones |
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265 | (1) |
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Addition of Grignard Reagents and Acetylides |
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265 | (3) |
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Addition of Hydrogen Cyanide; Cyanohydrins |
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268 | (1) |
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Addition of Nitrogen Nucleophiles |
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269 | (1) |
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Reduction of Carbonyl Compounds |
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270 | (1) |
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Oxidation of Carbonyl Compounds |
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271 | (1) |
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272 | (2) |
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Acidity of α-Hydrogens; the Enolate Anion |
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274 | (1) |
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Deuterium Exchange in Carbonyl Compounds |
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275 | (1) |
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276 | (1) |
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The Mixed Aldol Condensation |
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277 | (2) |
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A Word About Water Treatment and the Chemistry of Enols/Enolates |
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278 | (1) |
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Commercial Synthesis Via the Aldol Condensation |
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279 | (6) |
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280 | (1) |
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281 | (1) |
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281 | (4) |
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Carboxylic Acids and Their Derivatives |
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285 | (40) |
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286 | (3) |
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Physical Properties of Acids |
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289 | (1) |
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Acidity and Acidity Constants |
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290 | (1) |
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What Makes Carboxylic Acids Acidic? |
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291 | (2) |
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Effect of Structure on Acidity; the Inductive Effect Revisited |
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293 | (1) |
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Conversion of Acids to Salts |
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294 | (1) |
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294 | (5) |
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Oxidation of Primary Alcohols and Aldehydes |
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295 | (1) |
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Oxidation of Aromatic Side Chains |
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295 | (1) |
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Reaction of Grignard Reagents with Carbon Dioxide |
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296 | (1) |
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Hydrolysis of Cyanides (Nitriles) |
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296 | (1) |
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A Word About Green Chemistry and Ibuprofen: A Case Study |
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297 | (1) |
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A Closer Look at Green Chemistry |
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298 | (1) |
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Carboxylic Acid Derivatives |
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299 | (1) |
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299 | (1) |
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Preparation of Esters; Fischer Esterification |
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300 | (1) |
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The Mechanism of Acid-Catalyzed Esterification; Nucleophilic Acyl Substitution |
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301 | (2) |
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303 | (1) |
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304 | (1) |
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305 | (1) |
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Reaction of Esters with Grignard Reagents |
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305 | (1) |
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306 | (1) |
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The Need for Activated Acyl Compounds |
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306 | (1) |
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307 | (2) |
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309 | (2) |
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A Word About Thioesters, Nature's Acyl-Activating Groups |
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311 | (1) |
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311 | (3) |
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A Summary of Carboxylic Acid Derivatives |
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314 | (2) |
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The α-Hydrogen of Esters; the Claisen Condensation |
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316 | (9) |
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319 | (1) |
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320 | (1) |
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320 | (5) |
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Amines and Related Nitrogen Compounds |
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325 | (28) |
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Classification and Structure of Amines |
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326 | (1) |
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327 | (1) |
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Physical Properties and Intermolecular Interactions of Amines |
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328 | (1) |
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Preparation of Amines; Alkylation of Ammonia and Amines |
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329 | (2) |
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Preparation of Amines; Reduction of Nitrogen Compounds |
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331 | (2) |
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333 | (3) |
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Comparison of the Basicity and Acidity of Amines and Amides |
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336 | (1) |
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Reaction of Amines with Strong Acids; Amine Salts |
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337 | (3) |
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A Word About Alkaloids and the Dart-Poison Frogs |
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339 | (1) |
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Chiral Amines as Resolving Agents |
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340 | (1) |
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Acylation of Amines with Acid Derivatives |
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341 | (1) |
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Quaternary Ammonium Compounds |
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342 | (1) |
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Aromatic Diazonium Compounds |
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343 | (3) |
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346 | (7) |
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348 | (1) |
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349 | (1) |
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349 | (4) |
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Spectroscopy and Structure Determination |
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353 | (35) |
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Principles of Spectroscopy |
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354 | (2) |
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Nuclear Magnetic Resonance Spectroscopy (NMR) |
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356 | (9) |
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Measuring an NMR Spectrum |
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356 | (1) |
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Chemical Shifts and Peak Areas |
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357 | (4) |
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361 | (4) |
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365 | (4) |
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A Word About NMR in Biology and Medicine |
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366 | (3) |
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369 | (4) |
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Visible and Ultraviolet Spectroscopy |
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373 | (3) |
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376 | (12) |
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A Closer Look at Mass Spectrometry and Carbon Dating |
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379 | (1) |
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380 | (8) |
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388 | (21) |
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Pyridine: Bonding and Basicity |
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389 | (1) |
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390 | (3) |
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Other Six-Membered Heterocycles |
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393 | (3) |
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Five-Membered Heterocycles: Furan, Pyrrole, and Thiophene |
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396 | (2) |
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Electrophilic Substitution in Furan, Pyrrole, and Thiophene |
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398 | (1) |
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Other Five-Membered Heterocycles: Azoles |
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399 | (2) |
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A Word About Porphyrins: What Makes Blood Red and Grass Green? |
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400 | (1) |
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Fused-Ring, Five-Membered Heterocycles: Indoles and Purines |
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401 | (8) |
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A Word About Morphine and Other Nitrogen-Containing Drugs |
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403 | (2) |
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405 | (1) |
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406 | (1) |
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406 | (3) |
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409 | (27) |
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Classification of Polymers |
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410 | (1) |
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Free-Radical Chain-Growth Polymerization |
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410 | (6) |
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Cationic Chain-Growth Polymerization |
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416 | (1) |
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Anionic Chain-Growth Polymerization |
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417 | (1) |
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Stereoregular Polymers; Ziegler--Natta Polymerization |
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418 | (2) |
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A Word About Polyacetylene and Conducting Polymers |
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419 | (1) |
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Diene Polymers: Natural and Synthetic Rubber |
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420 | (2) |
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422 | (1) |
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Step-Growth Polymerization: Dacron and Nylon |
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423 | (4) |
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A Word About Degradable Polymers |
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424 | (1) |
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A Word About Aramids, the Latest in Polyamides |
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425 | (2) |
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427 | (1) |
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Polyurethanes and Other Step-Growth Polymers |
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427 | (9) |
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431 | (1) |
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432 | (1) |
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433 | (3) |
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436 | (22) |
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Fats and Oils; Triesters of Glycerol |
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437 | (3) |
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Hydrogenation of Vegetable Oils |
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440 | (1) |
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Saponification of Fats and Oils; Soap |
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441 | (1) |
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442 | (1) |
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Synthetic Detergents (Syndets) |
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443 | (4) |
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A Word About Commercial Detergents |
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445 | (2) |
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447 | (1) |
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Prostaglandins, Leukotrienes, and Lipoxins |
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448 | (2) |
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A Word About Prostaglandins, Aspirin, and Pain |
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448 | (2) |
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450 | (1) |
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450 | (8) |
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455 | (1) |
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455 | (3) |
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458 | (31) |
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Definitions and Classification |
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459 | (1) |
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459 | (1) |
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Chirality in Monosaccharides; Fischer Projection Formulas and D,L-Sugars |
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460 | (4) |
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The Cyclic Hemiacetal Structures of Monosaccharides |
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464 | (2) |
|
Anomeric Carbons; Mutarotation |
|
|
466 | (1) |
|
Pyranose and Furanose Structures |
|
|
467 | (1) |
|
Conformations of Pyranoses |
|
|
468 | (1) |
|
Esters and Ethers from Monosaccharides |
|
|
469 | (1) |
|
Reduction of Monosaccharides |
|
|
470 | (1) |
|
Oxidation of Monosaccharides |
|
|
470 | (1) |
|
Formation of Glycosides from Monosaccharides |
|
|
471 | (2) |
|
|
|
473 | (5) |
|
|
|
473 | (1) |
|
|
|
474 | (1) |
|
|
|
474 | (1) |
|
|
|
475 | (2) |
|
A Word About Sweetness and Sweeteners |
|
|
477 | (1) |
|
|
|
478 | (4) |
|
|
|
478 | (1) |
|
|
|
479 | (1) |
|
A Word About Fat Substitutes from Carbohydrates |
|
|
480 | (1) |
|
|
|
481 | (1) |
|
|
|
482 | (1) |
|
|
|
482 | (1) |
|
|
|
482 | (1) |
|
Ascorbic Acid (Vitamin C) |
|
|
483 | (6) |
|
|
|
484 | (1) |
|
|
|
485 | (4) |
|
Amino Acids, Peptides, and Proteins |
|
|
489 | (35) |
|
Naturally Occurring Amino Acids |
|
|
490 | (2) |
|
The Acid--Base Properties of Amino Acids |
|
|
492 | (3) |
|
The Acid--Base Properties of Amino Acids with More Than One Acidic or Basic Group |
|
|
495 | (2) |
|
|
|
497 | (1) |
|
|
|
497 | (1) |
|
|
|
498 | (1) |
|
|
|
499 | (2) |
|
A Word About Some Naturally Occurring Peptides |
|
|
500 | (1) |
|
|
|
501 | (1) |
|
|
|
502 | (1) |
|
The Primary Structure of Proteins |
|
|
502 | (4) |
|
|
|
502 | (1) |
|
|
|
503 | (2) |
|
Cleavage of Selected Peptide Bonds |
|
|
505 | (1) |
|
The Logic of Sequence Determination |
|
|
506 | (2) |
|
A Word About Protein Sequencing and Evolution |
|
|
507 | (1) |
|
|
|
508 | (4) |
|
Secondary Structure of Proteins |
|
|
512 | (2) |
|
Geometry of the Peptide Bond |
|
|
512 | (1) |
|
|
|
512 | (1) |
|
The α Helix and the Pleated Sheet |
|
|
513 | (1) |
|
Tertiary Structure: Fibrous and Globular Proteins |
|
|
514 | (2) |
|
Quaternary Protein Structure |
|
|
516 | (8) |
|
A Closer Look At Nobel Laureates and Protein Chemistry |
|
|
517 | (1) |
|
|
|
518 | (1) |
|
|
|
519 | (5) |
|
Nucleotides and Nucleic Acids |
|
|
524 | (24) |
|
The General Structure of Nucleic Acids |
|
|
525 | (1) |
|
Components of Deoxyribonucleic Acid (DNA) |
|
|
525 | (1) |
|
|
|
526 | (2) |
|
|
|
528 | (1) |
|
The Primary Structure of DNA |
|
|
529 | (1) |
|
|
|
530 | (2) |
|
A Word About DNA and Crime |
|
|
531 | (1) |
|
Laboratory Synthesis of Nucleic Acids |
|
|
532 | (1) |
|
Secondary DNA Structure; the Double Helix |
|
|
532 | (2) |
|
|
|
534 | (2) |
|
A Closer Look At The Polymerase Chain Reaction (PCR) |
|
|
536 | (1) |
|
|
|
536 | (2) |
|
The Genetic Code and Protein Biosynthesis |
|
|
538 | (4) |
|
A Word About The Human Genome |
|
|
539 | (1) |
|
A Word About Nucleic Acids and Viruses |
|
|
540 | (2) |
|
Other Biologically Important Nucleotides |
|
|
542 | (6) |
|
|
|
545 | (1) |
|
|
|
545 | (3) |
| Photo Credits |
|
548 | (1) |
| Appendix |
|
549 | (1) |
| Table A: Bond Energies for the Dissociation of Selected Bonds in the Reaction A---X → A. + X. (in kcal/mol) |
|
549 | (1) |
| Table B: Bond Lengths of Selected Bonds (in angstroms, A) |
|
549 | (1) |
| Table C: Typical Acidities of Organic Functional Groups |
|
550 | (2) |
| Index/Glossary |
|
552 | |
