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Structure and Bonding in Alkanes |
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2 | (42) |
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The Development and Study of Organic Chemistry |
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4 | (4) |
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The Formation of Molecules |
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8 | (14) |
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8 | (4) |
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12 | (2) |
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14 | (5) |
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19 | (1) |
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20 | (1) |
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Drawing Three-Dimensional Structures |
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21 | (1) |
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22 | (4) |
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Properties of Hydrocarbons |
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23 | (1) |
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Alkanes (Saturated Hydrocarbons) |
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23 | (1) |
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24 | (2) |
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26 | (1) |
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26 | (2) |
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28 | |
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10 | (4) |
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30 | (1) |
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Straight-Chain Hydrocarbons |
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31 | (1) |
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31 | (1) |
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31 | (3) |
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34 | |
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14 | (28) |
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34 | (2) |
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36 | (1) |
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37 | (1) |
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37 | (2) |
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39 | (3) |
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Alkenes, Aromatic Hydrocarbons, and Alkynes |
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42 | (44) |
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44 | (18) |
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44 | (1) |
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45 | (1) |
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45 | (1) |
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45 | (4) |
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49 | (3) |
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52 | (1) |
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52 | (4) |
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56 | (6) |
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62 | (2) |
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64 | (11) |
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65 | (2) |
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67 | (2) |
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Aromaticity and Huckel's Rule |
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69 | (2) |
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71 | (2) |
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Nomenclature for Aromatic Hydrocarbons |
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73 | (2) |
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75 | (11) |
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75 | (1) |
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76 | (2) |
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78 | (1) |
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79 | (1) |
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80 | (1) |
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80 | (1) |
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80 | (2) |
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82 | (4) |
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Functional Groups Containing Heteroatoms |
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86 | (68) |
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Compounds Containing sp3-Hybridized Nitrogen |
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87 | (5) |
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Ammonia: Hybridization and Geometry |
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88 | (1) |
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89 | (3) |
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Polar Covalent Bonding in Amines |
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92 | (9) |
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92 | (1) |
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93 | (2) |
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95 | (2) |
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Acidity and Basicity of Amines |
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97 | (3) |
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100 | (1) |
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Compounds Containing sp2-Hybridized Nitrogen |
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101 | (6) |
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Double Bonding at Nitrogen |
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101 | (1) |
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Bond Strengths of Multiple Bonds |
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102 | (1) |
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Calculating Oxidation Levels |
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103 | (4) |
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Compounds Containing sp-Hybridized Nitrogen |
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107 | (1) |
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Compounds Containing sp3-Hybridized Oxygen |
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108 | (5) |
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108 | (1) |
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109 | (3) |
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112 | (1) |
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113 | (11) |
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Homolytic Cleavage: Bond Energies and Radical Structure |
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115 | (2) |
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117 | (1) |
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Heterolytic Cleavage of C---OH Bonds: Carbocation Formation |
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118 | (2) |
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120 | (1) |
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Ordering Alcohol Reactivity by Class |
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120 | (1) |
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Conjugation in Cations and Radicals |
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121 | (3) |
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Bond Formation: Nucleophiles and Electrophiles |
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124 | (1) |
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Carbonyl Compounds (Aldehydes and Ketones): R2C=O |
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125 | (1) |
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126 | (1) |
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126 | (5) |
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Derivatives of Carboxylic Acids |
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127 | (3) |
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130 | (1) |
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Sulfur-Containing Compounds |
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131 | (2) |
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Aromatic Compounds Containing Heteroatoms |
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133 | (5) |
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Biologically Important Heteroaromatics |
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134 | (3) |
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Heteroatom-Substituted Arenes |
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137 | (1) |
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138 | (2) |
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Solvents for Organic Chemistry |
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140 | (1) |
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Nomenclature for Functional Groups |
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141 | (13) |
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143 | (2) |
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145 | (1) |
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145 | (2) |
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147 | (7) |
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Chromatography and Spectroscopy: Purification and Structure Determination |
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154 | (62) |
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Using Physical Properties to Establish Structure |
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155 | (2) |
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Purification of Compounds |
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156 | (1) |
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Determination of Structure |
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157 | (1) |
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157 | (8) |
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Partitioning and Extraction |
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158 | (1) |
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Liquid Chromatography on Stationary Columns |
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158 | (2) |
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160 | (1) |
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Paper and Thin-Layer Chromatography |
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161 | (1) |
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Reverse-Phase Chromatography |
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162 | (1) |
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162 | (1) |
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163 | (2) |
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165 | (51) |
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Nuclear Magnetic Resonance (NMR) Spectroscopy |
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166 | (2) |
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168 | (3) |
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171 | (17) |
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Infrared (IR) Spectroscopy |
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188 | (10) |
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Visible and Ultraviolet (UV) Spectroscopy |
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198 | (7) |
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205 | (3) |
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208 | (1) |
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209 | (2) |
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211 | (5) |
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216 | (52) |
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Geometric Isomerization: Rotation about Pi Bonds |
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218 | (4) |
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218 | (1) |
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Energetics of Rotation about Pi Bonds |
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219 | (1) |
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220 | (1) |
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Light-Induced Isomerization of Alkenes |
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221 | (1) |
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Geometric Isomerization to the Less Stable Isomer |
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222 | (1) |
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Conformational Analysis: Rotation about Sigma Bonds |
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222 | (8) |
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223 | (2) |
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225 | (5) |
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230 | (2) |
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232 | (9) |
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232 | (4) |
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Monosubstituted Cyclohexanes |
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236 | (2) |
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Disubstituted Cyclohexanes |
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238 | (2) |
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Fused Six-Member Rings: Decalins |
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240 | (1) |
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241 | (4) |
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243 | (1) |
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Representing Enantiomers in Two Dimensions |
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244 | (1) |
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245 | (2) |
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247 | (4) |
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248 | (2) |
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250 | (1) |
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Designating Configuration |
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251 | (6) |
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A Single Center of Chirality: Relative Configuration |
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251 | (1) |
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Multiple Centers of Chirality: Absolute Configuration |
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252 | (1) |
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Resolution of Enantiomers |
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253 | (1) |
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254 | (2) |
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256 | (1) |
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Stereoisomerism at Heteroatom Centers |
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257 | (1) |
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Optical Activity in Allenes |
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258 | (10) |
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259 | (1) |
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260 | (1) |
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261 | (2) |
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263 | (5) |
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Understanding Organic Reactions |
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268 | (50) |
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Reaction Profiles (Energy Diagrams) |
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269 | (4) |
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270 | (1) |
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Thermodynamics: Initial and Final States |
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270 | (1) |
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Kinetics: The Reaction Pathway |
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271 | (1) |
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271 | (1) |
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272 | (1) |
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273 | (6) |
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Enthalpy Effects: Keto-Enol Tautomerization |
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274 | (2) |
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Entropy Effects: The Diels-Alder Reaction |
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276 | (3) |
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Characterizing Transition States: The Hammond Postulate |
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279 | (1) |
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Types of Reactive Intermediates |
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279 | (6) |
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Carbocations and Radicals |
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280 | (1) |
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280 | (2) |
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282 | (1) |
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283 | (2) |
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Kinetics: Relative Rates from Reaction Profiles |
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285 | (2) |
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Kinetic and Thermodynamic Control |
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287 | (4) |
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291 | (3) |
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Relating Free Energy to an Equilibrium Constant |
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291 | (1) |
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292 | (2) |
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294 | (11) |
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A Quantitative Measure of Thermodynamic Equilibria |
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294 | (3) |
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297 | (1) |
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297 | (1) |
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Inductive and Steric Effects |
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297 | (3) |
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300 | (1) |
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300 | (2) |
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302 | (1) |
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303 | (2) |
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Reaction Rates: Understanding Kinetics |
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305 | (13) |
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306 | (1) |
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Boltzmann Energy Distributions |
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307 | (2) |
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309 | (1) |
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310 | (1) |
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310 | (1) |
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311 | (3) |
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314 | (4) |
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Mechanisms of Organic Reactions |
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318 | (52) |
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Classification of Reactions |
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320 | (5) |
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320 | (1) |
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320 | (1) |
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321 | (1) |
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321 | (1) |
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322 | (1) |
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322 | (1) |
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323 | (1) |
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Oxidation-Reduction Reactions |
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323 | (1) |
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324 | (1) |
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Bond Making and Bond Breaking: Thermodynamic Feasibility |
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325 | (4) |
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Energy Changes in Homolytic Reactions |
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325 | (2) |
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Energy Changes in Heterolytic Reactions |
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327 | (2) |
|
How to Study a New Organic Reaction |
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329 | (2) |
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Mechanism of a Concerted Reaction: Bimolecular Nucleophilic Substitution (SN2) |
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331 | (11) |
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The Transition State of an SN2 Reaction |
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333 | (2) |
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Inversion of Configuration |
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335 | (1) |
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Nonsymmetrical SN2 Transition States |
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336 | (1) |
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Factors Affecting the Rate of SN2 Reactions |
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337 | (4) |
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Synthetic Utility of SN2 Reactions |
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341 | (1) |
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Mechanism of Two Multistep Heterolytic Reactions: Electrophilic Addition and Nucleophilic Substitution (SN1) |
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342 | (10) |
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Electrophilic Addition of HCl to an Alkene |
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342 | (3) |
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Multistep Nucleophilic Substitution (SN1): Hydrolysis of Alkyl Bromides |
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345 | (4) |
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Factors Affecting the Rate of SN1 Reactions |
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349 | (1) |
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350 | (2) |
|
Mechanism of a Multistep Homolytic Cleavage: Free-Radical Halogenation of Alkanes |
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352 | (9) |
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Energetics of Homolytic Substitution in the Chlorination of Ethane |
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352 | (1) |
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Steps in a Radical Chain Reaction |
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353 | (2) |
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Relative Reactivity of Halogens |
|
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355 | (2) |
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Regiocontrol in Homolytic Substitution |
|
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357 | (4) |
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361 | (9) |
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363 | (1) |
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364 | (3) |
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367 | (3) |
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Substitution by Nucleophiles at sp3-Hybridized Carbon |
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370 | (48) |
|
Review of Mechanisms of Nucleophilic Substitution |
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372 | (3) |
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372 | (1) |
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372 | (1) |
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Solvents for Organic Reactions |
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373 | (2) |
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Competition between SN2 and SN1 Pathways |
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375 | (2) |
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Functional-Group Transformations through SN2 and SN1 Reactions |
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377 | (19) |
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Substitution of Halogen to Form Alcohols by an SN2 Mechanism |
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377 | (2) |
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Substitution of Halogen to Form Alcohols by an SN1 Mechanism |
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379 | (2) |
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Substitution of Halogen to Form Ethers: Williamson Ether Synthesis |
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381 | (2) |
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Sulfonate Esters as Leaving Groups for Substitution Reactions |
|
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383 | (1) |
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Substitution of Alcohols to Form Alkyl Halides |
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384 | (4) |
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Substitution of Halogen to Form Thiols and Thioethers |
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388 | (2) |
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Substitution of Halogen to Form Amines |
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390 | (4) |
|
Substitution of Halogen by Phosphines |
|
|
394 | (2) |
|
Preparation and Use of Carbon Nucleophiles |
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|
396 | (9) |
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397 | (1) |
|
General Methods for Preparation of Carbon Nucleophiles |
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397 | (1) |
|
sp-Hybridized Carbon Nucleophiles: Cyanide and Acetylide Anion |
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|
398 | (2) |
|
sp2- and sp3-Hybridized Carbon Nucleophiles: Organometallic Compounds |
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400 | (3) |
|
Reaction of Organometallic Compounds as Bases |
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403 | (2) |
|
Synthetic Methods: Functional-Group Conversion |
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405 | (1) |
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405 | (13) |
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409 | (1) |
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410 | (1) |
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411 | (2) |
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413 | (5) |
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418 | (48) |
|
Mechanistic Options for Elimination Reactions |
|
|
420 | (6) |
|
E1 Mechanism: Carbocation Intermediates |
|
|
420 | (3) |
|
E2 Mechanism: Synchronous Elimination |
|
|
423 | (1) |
|
E1cB Mechanism: Carbanion Intermediates |
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|
423 | (2) |
|
Transition States and Reaction Profiles for E1 and E2 Eliminations |
|
|
425 | (1) |
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|
426 | (2) |
|
Dehydration via an E1 Mechanism |
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426 | (1) |
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Dehydration via an E2 Mechanism |
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|
427 | (1) |
|
Dehydration via an E1cB Mechanism |
|
|
427 | (1) |
|
Summary of Alcohol Dehydration Reactions |
|
|
428 | (1) |
|
E2 Elimination Reactions: Dehydrohalogenation of Alkyl Halides |
|
|
428 | (9) |
|
Transition State for E2 Elimination: Anti-periplanar Relationship |
|
|
428 | (1) |
|
Stereochemistry of E2 Elimination Reactions |
|
|
429 | (2) |
|
Regiochemistry of E2 Elimination Reactions |
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|
431 | (1) |
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Effect of Reaction Conditions on Regiochemistry in E2 Reactions |
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|
431 | (4) |
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Effect of Substrate Structure on the Regiochemistry of E2 Elimination in Cyclohexane Rings |
|
|
435 | (2) |
|
Summary of E2 Elimination |
|
|
437 | (1) |
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|
437 | (3) |
|
Intermediate Cations in E1 Elimination Reactions |
|
|
437 | (1) |
|
Stereochemistry of E1 Elimination Reactions |
|
|
437 | (1) |
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Factors Affecting Regioselectivity in E1 Reactions |
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438 | (2) |
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Competing Rearrangements in E1 Reactions |
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440 | (3) |
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441 | (1) |
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441 | (1) |
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441 | (2) |
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443 | (1) |
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Elimination of HX from Vinyl Halides |
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443 | (3) |
|
E1 Elimination of HX from Vinyl Halides |
|
|
444 | (1) |
|
E1cB and E2 Elimination of HX from Vinyl Halides |
|
|
445 | (1) |
|
Preparation and Use of Vinyl Halides |
|
|
445 | (1) |
|
Elimination of HX from Aryl Halides: Formation and Reactions of Benzyne |
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|
446 | (2) |
|
Mechanisms of Elimination from Aryl Halides |
|
|
446 | (1) |
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447 | (1) |
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447 | (1) |
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|
448 | (4) |
|
Oxidation of Alcohols with Chromium Reagents |
|
|
448 | |
|
Functional Group Conversions Using Chromate Oxidations |
|
|
50 | (401) |
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|
|
451 | (1) |
|
Oxidation of Hydrocarbons: Dehydrogenation |
|
|
452 | (3) |
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|
|
452 | (1) |
|
Laboratory-Scale Dehydrogenation |
|
|
452 | (3) |
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455 | (11) |
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457 | (1) |
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458 | (1) |
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|
458 | (3) |
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|
|
461 | (5) |
|
Addition to Carbon-Carbon Multiple Bonds |
|
|
466 | (56) |
|
Electrophilic Addition of HC1, HBr, and H2O |
|
|
|
Mechanism of Electrophilic Addition |
|
|
468 | (3) |
|
|
|
471 | (3) |
|
Regiochemistry of Electrophilic Addition |
|
|
474 | (2) |
|
Addition to Conjugated Dienes |
|
|
476 | (1) |
|
Stereochemistry of Electrophilic Addition |
|
|
477 | (2) |
|
|
|
479 | (1) |
|
Addition of HX to Alkynes: Formation of Geminal Dihalides |
|
|
480 | (2) |
|
Addition of Other Electrophiles |
|
|
482 | (8) |
|
Oxymercuration--Demercuration |
|
|
482 | (3) |
|
|
|
485 | (1) |
|
|
|
485 | (4) |
|
Carbocations as Electrophiles |
|
|
489 | (1) |
|
|
|
490 | (3) |
|
Radical Addition of HBr: Reversing Markovnikov Regiochemistry |
|
|
490 | (2) |
|
|
|
492 | (1) |
|
|
|
493 | (14) |
|
Synthesis of Cyclopropanes |
|
|
493 | (2) |
|
|
|
495 | (2) |
|
Four-Member Cyclic Transition State: Hydroboration-Oxidation |
|
|
497 | (3) |
|
Five-Member Cyclic Intermediates |
|
|
500 | (3) |
|
Formation of Six-Member Rings: The Diels-Alder Reaction |
|
|
503 | (2) |
|
Stereochemistry in the Diels-Alder Reaction |
|
|
505 | (2) |
|
Reduction of Multiple Bonds |
|
|
507 | (6) |
|
|
|
508 | (3) |
|
Dissolving-Metal Reductions |
|
|
511 | (2) |
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|
|
513 | (9) |
|
|
|
515 | (1) |
|
|
|
516 | (1) |
|
|
|
517 | (3) |
|
|
|
520 | (2) |
|
Electrophilic Aromatic Substitution |
|
|
522 | (48) |
|
Mechanism of Electrophilic Aromatic Substitution |
|
|
524 | (1) |
|
Step 1: Addition of the Electrophile and Formation of a Pentadienyl Cation as Intermediate |
|
|
524 | (1) |
|
|
|
525 | (1) |
|
Introduction of Groups by Electrophilic Aromatic Substitution: Activated Electrophiles |
|
|
525 | (9) |
|
|
|
526 | (1) |
|
|
|
527 | (1) |
|
|
|
528 | (1) |
|
Friedel-Crafts Alkylation |
|
|
528 | (4) |
|
|
|
532 | (2) |
|
Reactions of Substituents and Side Chains of Aromatic Rings |
|
|
534 | (5) |
|
Reduction of Nitro Groups to Primary Amines |
|
|
534 | (1) |
|
|
|
535 | (3) |
|
Oxidation of Carbon Side Chains |
|
|
538 | (1) |
|
Reactions of Aryl Side Chains |
|
|
538 | (1) |
|
Substituent Effects in Aromatic Compounds: Reactivity and Orientation |
|
|
539 | (16) |
|
Weakly Activating Substituents: Alkyl Groups |
|
|
540 | (4) |
|
Strongly Activating Heteroatom Substituents |
|
|
544 | (2) |
|
Moderately Activating Heteroatom Substituents |
|
|
546 | (1) |
|
Moderately Deactivating Substituents: The Halogens |
|
|
546 | (2) |
|
Moderately and Strongly Deactivating Substituents |
|
|
548 | (1) |
|
Summary of Substituent Effects |
|
|
549 | (1) |
|
Activating/Deactivating Versus Directing Effects |
|
|
550 | (1) |
|
|
|
551 | (1) |
|
Using Substituent Effects in Synthesis |
|
|
552 | (3) |
|
Electrophilic Attack on Polycyclic Aromatic Compounds |
|
|
555 | (2) |
|
|
|
557 | (3) |
|
|
|
560 | (10) |
|
|
|
561 | (1) |
|
|
|
561 | (1) |
|
|
|
562 | (2) |
|
|
|
564 | (6) |
|
Nucleophilic Addition and Substitution at Carbonyl Groups |
|
|
570 | (68) |
|
Nucleophilic Addition to a Carbonyl Group |
|
|
571 | (5) |
|
|
|
571 | (2) |
|
Possible Reactions of a Nucleophile with a Carbonyl Group |
|
|
573 | (1) |
|
|
|
574 | (2) |
|
Nucleophilic Addition of Hydrogen to Carbonyl Groups |
|
|
576 | (8) |
|
Complex Metal Hydride Reductions |
|
|
576 | (6) |
|
Relative Reactivity of Carbonyl Compounds toward Hydride Reducing Agents |
|
|
582 | (2) |
|
|
|
584 | (9) |
|
Addition of Water: Hydrate Formation |
|
|
584 | (3) |
|
Addition of Hydroxide Ion: The Cannizzaro Reaction and Hydride Transfer |
|
|
587 | (2) |
|
|
|
589 | (4) |
|
|
|
593 | (6) |
|
|
|
593 | (4) |
|
Other Nitrogen Nucleophiles |
|
|
597 | (2) |
|
Nucleophilic Acyl Substitution of Carboxylic Acids and Derivatives |
|
|
599 | (11) |
|
Relative Stability of Carboxylic Acid Derivatives |
|
|
600 | (1) |
|
Interconversion of Carboxylic Acid Derivatives |
|
|
601 | (5) |
|
Carboxylic Acid Chlorides |
|
|
606 | (3) |
|
Reactions of Acid Anhydrides |
|
|
609 | (1) |
|
Hydrolysis of Nitriles to Carboxylic Acids |
|
|
609 | (1) |
|
Derivatives of Sulfonic and Phosphoric Acids |
|
|
610 | (3) |
|
Sulfonic Acid Derivatives |
|
|
610 | (2) |
|
Phosphoric Acid Derivatives |
|
|
612 | (1) |
|
|
|
613 | (8) |
|
|
|
613 | (2) |
|
|
|
615 | (3) |
|
|
|
618 | (1) |
|
|
|
618 | (3) |
|
|
|
621 | (1) |
|
|
|
621 | (17) |
|
|
|
626 | (1) |
|
|
|
627 | (1) |
|
|
|
628 | (3) |
|
|
|
631 | (7) |
|
Substitution Alpha to Carbonyl Groups: Enolate Anions and Enols as Nucleophiles |
|
|
638 | (40) |
|
Formation and Reactions of Enolate Anions and Enols |
|
|
640 | (7) |
|
Molecular Orbitals of Enolate Anions |
|
|
640 | (1) |
|
Structure of Enolate Anions |
|
|
641 | (1) |
|
Protonation of Enolate Anions |
|
|
641 | (2) |
|
Halogenation Alpha to Carbonyl Groups |
|
|
643 | (3) |
|
Kinetic versus Thermodynamic Deprotonation of Carbonyl Groups |
|
|
646 | (1) |
|
Alkylation of Ketones and Esters: SN2 Reaction with Alkyl Halides |
|
|
647 | (2) |
|
Aldol Reaction, Aldol Condensation, and Related Reactions: Nucleophilic Addition of Enolate Anions to Carbonyl Groups |
|
|
649 | (9) |
|
|
|
649 | (1) |
|
|
|
650 | (1) |
|
Aldol Reaction and Aldol Condensation of Ketones |
|
|
650 | (1) |
|
Intramolecular Aldol Reaction and Aldol Condensation |
|
|
651 | (1) |
|
|
|
652 | (2) |
|
Nucleophilic Addition to α,ß-Unsaturated Carbonyl Groups: Conjugate Addition |
|
|
654 | (4) |
|
The Claisen Condensation and Related Reactions: Acylation of Esters |
|
|
658 | (4) |
|
|
|
658 | (1) |
|
The Dieckmann Condensation |
|
|
659 | (1) |
|
Crossed Claisen Condensation |
|
|
660 | (1) |
|
|
|
661 | (1) |
|
Alkylation of ß-Dicarbonyl Compounds |
|
|
662 | (7) |
|
|
|
662 | (1) |
|
Alkylation of ß-Ketoesters |
|
|
663 | (1) |
|
Alkylation of Malonic Acid Diesters |
|
|
664 | (1) |
|
Hydrolysis and Decarboxylation of ß-Ketoesters and Malonic Acid Diesters |
|
|
665 | (2) |
|
Acetoacetic Ester and Malonic Ester Syntheses |
|
|
667 | (1) |
|
Formation of Carbocyclic Rings Using Acetoacetic Ester and Malonic Ester Syntheses |
|
|
668 | (1) |
|
|
|
669 | (1) |
|
|
|
669 | (9) |
|
|
|
672 | (1) |
|
|
|
673 | (1) |
|
|
|
673 | (3) |
|
|
|
676 | (2) |
|
Skeletal-Rearrangement Reactions |
|
|
678 | (40) |
|
Carbon-Carbon Rearrangements |
|
|
679 | (11) |
|
|
|
680 | (4) |
|
|
|
684 | (1) |
|
Pericyclic Rearrangements |
|
|
685 | (5) |
|
Carbon-Nitrogen Rearrangements |
|
|
690 | (5) |
|
The Beckmann Rearrangement |
|
|
691 | (2) |
|
The Hofmann Rearrangement |
|
|
693 | (2) |
|
Carbon-Oxygen Rearrangements |
|
|
695 | (4) |
|
The Baeyer-Villiger Oxidation |
|
|
696 | (2) |
|
The Claisen Rearrangement |
|
|
698 | (1) |
|
|
|
699 | (19) |
|
|
|
700 | (1) |
|
|
|
700 | (1) |
|
Review of Reactions from Chapters 8--14 |
|
|
701 | (10) |
|
|
|
711 | (2) |
|
|
|
713 | (5) |
|
|
|
718 | (42) |
|
Grouping Chemical Reactions |
|
|
720 | (4) |
|
|
|
724 | (2) |
|
Designing a Synthesis by Working Backward |
|
|
724 | (1) |
|
Rationale for Retrosynthetic Analysis |
|
|
724 | (2) |
|
Reactions Requiring Both Functional-Group Transformation and Skeletal Construction |
|
|
726 | (2) |
|
Extending the Retrosynthetic Approach: Alternative Routes for Synthesizing |
|
|
|
|
|
728 | (1) |
|
Analyzing Individual Reactions in a Sequence |
|
|
728 | (1) |
|
Order of Chemical Transformations |
|
|
728 | (2) |
|
Selecting the Best Synthetic Route |
|
|
730 | (3) |
|
Criteria for Evaluating Synthetic Efficiency |
|
|
733 | (4) |
|
|
|
733 | (1) |
|
|
|
734 | (1) |
|
|
|
735 | (2) |
|
Real-World Synthetic Objectives |
|
|
737 | (4) |
|
Multifunctional Compounds |
|
|
737 | (2) |
|
Functional-Group Compatibility |
|
|
739 | (2) |
|
|
|
741 | (5) |
|
Protection of Aldehydes and Ketones |
|
|
741 | (1) |
|
Requirements for the Use of Protecting Groups |
|
|
742 | (1) |
|
|
|
743 | (1) |
|
Protection of Carboxylates |
|
|
743 | (1) |
|
|
|
744 | (1) |
|
Use of an Alcohol Protecting Group |
|
|
745 | (1) |
|
Practical Examples of Multistep Syntheses |
|
|
746 | (14) |
|
Phenylpropionic Acid Analogs: Ibuprofen and Ketoprofen |
|
|
746 | (2) |
|
|
|
748 | (4) |
|
|
|
752 | (1) |
|
|
|
752 | (1) |
|
|
|
753 | (2) |
|
|
|
755 | (5) |
|
|
|
760 | (42) |
|
|
|
761 | (2) |
|
Linear and Branched Polymers |
|
|
763 | (2) |
|
|
|
765 | (1) |
|
|
|
765 | (11) |
|
|
|
765 | (2) |
|
|
|
767 | (5) |
|
Cross-Linking in Polymers |
|
|
772 | (1) |
|
Heteroatom-Containing Addition Polymers |
|
|
773 | (3) |
|
|
|
776 | (7) |
|
|
|
776 | (1) |
|
|
|
777 | (2) |
|
|
|
779 | (2) |
|
|
|
781 | (1) |
|
|
|
782 | (1) |
|
Extensively Cross-Linked Polymers |
|
|
783 | (3) |
|
Three-Dimensional Structure of Polymers |
|
|
786 | (16) |
|
|
|
786 | (2) |
|
Naturally Occurring Polypeptides |
|
|
788 | (7) |
|
|
|
795 | (2) |
|
|
|
797 | (1) |
|
|
|
798 | (1) |
|
|
|
798 | (3) |
|
|
|
801 | (1) |
|
Naturally Occurring Oxygen-Containing Compounds |
|
|
802 | (44) |
|
|
|
803 | (16) |
|
|
|
803 | (11) |
|
|
|
814 | (4) |
|
|
|
818 | (1) |
|
|
|
819 | (6) |
|
|
|
820 | (1) |
|
Phosphates as Leaving Groups |
|
|
821 | (1) |
|
Biosynthetic Pathways Involving Phosphates |
|
|
822 | (2) |
|
Biosynthetic Pathways Involving Epoxides |
|
|
824 | (1) |
|
|
|
825 | (8) |
|
|
|
826 | (1) |
|
|
|
827 | (1) |
|
|
|
828 | (2) |
|
|
|
830 | (2) |
|
|
|
832 | (1) |
|
Dimeric and Polymeric Carbohydrates |
|
|
833 | (13) |
|
|
|
837 | (1) |
|
|
|
838 | (1) |
|
|
|
839 | (2) |
|
|
|
841 | (5) |
|
Naturally Occurring Nitrogen-Containing Compounds |
|
|
846 | (46) |
|
Methods for Forming Carbon-Nitrogen Bonds: A Review |
|
|
847 | (6) |
|
Amines via Nucleophilic Substitution |
|
|
848 | (1) |
|
|
|
848 | (1) |
|
|
|
849 | (1) |
|
|
|
850 | (2) |
|
Amines via Nitrile Reduction |
|
|
852 | (1) |
|
The Beckmann Rearrangement of Oximes: Amides from Carbonyl Compounds |
|
|
852 | (1) |
|
Amino Acids: Structure and Properties |
|
|
853 | (5) |
|
|
|
853 | (1) |
|
Properties of Amino Acids |
|
|
854 | (4) |
|
Polypeptides: Structure, Function, and Synthesis |
|
|
858 | (9) |
|
Structure and Function of Polypeptides |
|
|
585 | (275) |
|
Synthesis of Polypeptides |
|
|
860 | (7) |
|
Alkaloids: Structure and Biological Activity |
|
|
867 | (3) |
|
Structure of Nucleic Acids |
|
|
870 | (5) |
|
|
|
871 | (1) |
|
|
|
871 | (1) |
|
Attachment of Base to Sugar |
|
|
872 | (2) |
|
|
|
874 | (1) |
|
Aminocarbohydrates: Structure and Function |
|
|
875 | (1) |
|
|
|
876 | (16) |
|
|
|
877 | (4) |
|
|
|
881 | (2) |
|
|
|
883 | (1) |
|
|
|
883 | (1) |
|
|
|
884 | (2) |
|
|
|
886 | (6) |
|
Noncovalent Interactions and Molecular Recognition |
|
|
892 | (30) |
|
Nonpolar (Hydrophobic) Interactions |
|
|
893 | (2) |
|
Influence of van der Waals Interactions on Physical Properties |
|
|
834 | (60) |
|
Strength of van der Waals Interactions |
|
|
894 | (1) |
|
Origin of van der Waals Interactions |
|
|
895 | (1) |
|
|
|
895 | (13) |
|
Dipole-Dipole Interactions |
|
|
895 | (2) |
|
|
|
897 | (5) |
|
|
|
902 | (6) |
|
|
|
908 | (6) |
|
Hydrogen Bonding in Biopolymers |
|
|
908 | (1) |
|
Complementary Base Pairing |
|
|
909 | (1) |
|
|
|
910 | (1) |
|
|
|
911 | (1) |
|
|
|
912 | (1) |
|
Misreading the Genetic Code |
|
|
913 | (1) |
|
Molecular Recognition of Chiral Molecules |
|
|
914 | (8) |
|
Necessity of Three-Point Contact for Chiral Recognition |
|
|
914 | (3) |
|
Resolution of Enantiomers |
|
|
917 | (1) |
|
Biological Significance of Chirality |
|
|
917 | (2) |
|
|
|
919 | (1) |
|
|
|
919 | (2) |
|
|
|
921 | (1) |
|
|
|
922 | (42) |
|
General Concepts of Catalysis |
|
|
925 | (5) |
|
Transition-State Stabilization |
|
|
925 | (2) |
|
Effect of Solvation on SN2 Reactions |
|
|
927 | (3) |
|
Avoiding Charge Separation in Multistep Reactions |
|
|
930 | (5) |
|
Intermolecular Proton Transfer |
|
|
933 | (1) |
|
Proton Transfer via Charge Relay |
|
|
934 | (1) |
|
Distinction between Catalysis and Induction |
|
|
935 | (3) |
|
|
|
938 | (1) |
|
Comparison of Intermolecular and Intramolecular Reactions |
|
|
939 | (2) |
|
Transition-Metal Catalysis |
|
|
941 | (8) |
|
Catalytic Addition of Hydrogen to Alkenes |
|
|
941 | (5) |
|
Catalysis of Olefin Polymerization |
|
|
946 | (3) |
|
|
|
949 | (15) |
|
|
|
949 | (1) |
|
Catalysis by the Enzyme Chymotrypsin |
|
|
950 | (2) |
|
Stabilization of Transition States by Enzymes |
|
|
952 | (1) |
|
Enzymes and Chiral Recognition |
|
|
953 | (3) |
|
Artificial Enzymes: Catalytic Antibodies |
|
|
956 | (3) |
|
|
|
959 | (1) |
|
|
|
960 | (2) |
|
|
|
962 | (2) |
|
Cofactors for Biological Reactions |
|
|
964 | (30) |
|
|
|
966 | (1) |
|
Recycling of Biological Reagents |
|
|
966 | (2) |
|
Cofactors: Chemical Reagents for Biological Transformations |
|
|
968 | (1) |
|
Cofactors for Redox Reactions |
|
|
969 | (7) |
|
|
|
969 | (3) |
|
|
|
972 | (2) |
|
|
|
974 | (2) |
|
Acetyl CoA: Cofactor for Acyl Transfer |
|
|
976 | (1) |
|
|
|
976 | (1) |
|
Activation of Carboxylic Acids (as Thiol Esters) toward Nucleophilic Attack |
|
|
976 | (1) |
|
Tetrahydrofolic Acid: A One-Carbon Transfer Cofactor for Methylation of Nucleic Acids |
|
|
977 | (4) |
|
Structure and Function of Tetrahydrofolic Acid |
|
|
977 | (2) |
|
Transfer of a Methylene Fragment |
|
|
979 | (1) |
|
Reductive Methylation of Deoxyuridylic Acid to Form Deoxythymidylic Acid |
|
|
980 | (1) |
|
Thiamine Pyrophosphate and Lipoic Acid: Cofactors for the Decarboxylation of a-Ketoacids |
|
|
981 | (3) |
|
Mechanisms of Decarboxylation |
|
|
982 | (1) |
|
Structure and Function of the Cofactors Thiamine z Pyrophosphate and Lipoic Acid |
|
|
982 | (1) |
|
Decarboxylation of α-Ketoacids in Biological Systems |
|
|
983 | (1) |
|
Mimicking Biological Activation with Reverse-Polarity Reagents |
|
|
984 | (10) |
|
Analysis of Carbon Reactivity |
|
|
985 | (1) |
|
Analysis of Carbon Reactivity in ß-Ketoesters |
|
|
986 | (1) |
|
Analysis of Carbon Reactivity in α-Ketoesters |
|
|
987 | (1) |
|
|
|
988 | (2) |
|
|
|
990 | (1) |
|
|
|
990 | (2) |
|
|
|
992 | (2) |
|
Energy Storage in Organic Molecules |
|
|
994 | (44) |
|
|
|
995 | (5) |
|
Kinetics and Thermodynamics |
|
|
995 | (2) |
|
|
|
997 | (1) |
|
Multistep Transformations |
|
|
998 | (2) |
|
|
|
1000 | (1) |
|
Energy in Living Organisms |
|
|
1000 | (1) |
|
Energy Transfer via Phosphoric Acid Anhydrides |
|
|
1001 | (2) |
|
Energy Transfer through Redox Reactions |
|
|
1003 | (1) |
|
Energy Storage in Fatty Acid Biosynthesis |
|
|
1004 | (5) |
|
Carbon-Carbon Bond Formation |
|
|
1004 | (2) |
|
|
|
1006 | (1) |
|
Synthesis of Longer Chains |
|
|
1007 | (2) |
|
Energy Release in Fatty Acid Degradation |
|
|
1009 | (1) |
|
The Krebs Cycle: Release and Transfer of Energy from Acetate |
|
|
1010 | (7) |
|
Oxidative Decarboxylation: Overview of the Krebs Cycle |
|
|
1010 | (3) |
|
Prochiral Centers in Citric Acid |
|
|
1013 | (1) |
|
|
|
1014 | (3) |
|
Maximizing the Efficiency of Energy Release by Controlling Heat Release |
|
|
1017 | (2) |
|
Energy Release from Carbohydrates through Glycolysis |
|
|
1019 | (12) |
|
Isomerization of Glucose to Fructose |
|
|
1020 | (1) |
|
Cleavage of Fructose into Three-Carbon Fragments |
|
|
1021 | (4) |
|
Conversion of the Three-Carbon Fragments into Acetic Acid Derivatives |
|
|
1025 | (6) |
|
Biological Reactions in Energy Storage and Utilization |
|
|
1031 | (7) |
|
|
|
1033 | (1) |
|
|
|
1034 | (2) |
|
|
|
1036 | (2) |
|
Molecular Basis for Drug Action |
|
|
1038 | (43) |
|
Chemical Basis of Disease States |
|
|
1040 | (3) |
|
Intact Biological Systems as Chemical Factories |
|
|
1043 | (1) |
|
H2 Blockers: Modern Antacids |
|
|
1044 | (2) |
|
Neurologically Active Drugs: ß-Phenethylamines |
|
|
1046 | (3) |
|
|
|
1049 | (12) |
|
Blocking Synthesis of Tetrahydrofolic Acid |
|
|
1049 | (3) |
|
Disruption of Membrane Structure and Interference with Ion Balance across Membranes |
|
|
1052 | (2) |
|
Disruption of Bacterial Cell Walls |
|
|
1054 | (7) |
|
|
|
1061 | (4) |
|
|
|
1061 | (1) |
|
|
|
1061 | (2) |
|
Viral Replication: The ``Coup de Grace'' |
|
|
1063 | (1) |
|
Antiviral Therapy: Looking for a ``Magic Bullet'' |
|
|
1063 | (2) |
|
|
|
1065 | (2) |
|
Identification of Disease-Causing Agents |
|
|
1065 | (1) |
|
Diseases Caused by Prions |
|
|
1066 | (1) |
|
Protein Misfolding and Alzheimer's Disease |
|
|
1066 | (1) |
|
|
|
1067 | (10) |
|
Characteristics of Cancer |
|
|
1067 | (1) |
|
|
|
1068 | (1) |
|
Treatment of Cancer: Chemotherapeutic Agents |
|
|
1068 | (1) |
|
Drugs Affecting Nucleic Acid Synthesis |
|
|
1069 | (5) |
|
|
|
1074 | (3) |
|
Organic Chemistry: Retrospective and Prospects |
|
|
1077 | (4) |
|
|
|
1078 | (1) |
|
|
|
1078 | (3) |
| Appendix |
|
1081 | (10) |
| Glossary |
|
1091 | (22) |
| Index |
|
1113 | |
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