Contents Section H-Alkenes and alky repa 990 sym metric al alke op insymmet nes 112 cation stabilization 115 H6 Reduction and oxidation of alkenes 117 H7 Hydroboration of alkenes 121 H8 Electrophilic additions to alkynes 124 H9 Reduction of alkynes 127 H10 Alkylation of terminal alkynes 129 H11 Conjugated dienes Section I- Aromatic chemistry 185 of honz ne 139 is of m 147 Electrophilic substitutions of mono-substituted aromatic rings 150 Synthesis of di-and tri-substituted benzenes 160 7 Oxidation and reduction 164 Section] Aldehydes and ketones 167 Preparat on ilic additi ilic ad arged nucleophiles Nucleon ogen nucleophiles and sulf 187 Reactions of enolate ions g-Halogenation 198 Reduction and oxidation I11 aB-Unsaturated aldehvdes and ketones 202 Section K-Carboxylic acids and carboxylic acid derivatives 205 KI and 205 K2 209 K3 Reactivity 213 K4 Preparations of carboxylic acids 217 K5 Preparations of carboxylic acid derivatives 219 K6 Reactions 224 K7 Enolate reactions 234 Section L-Alkyl halides 1 and physical properties of alkyl halides ohilic suhs ution 242 3 Factors affecting S2 versus S1 reactions 247 Elimination 252 Elimination versus substitution 256 L6 Reactions of alkyl halides 258 Organometallic reactions 261 Section H – Alkenes and alkynes 99 H1 Preparation of alkenes and alkynes 99 H2 Properties of alkenes and alkynes 101 H3 Electrophilic addition to symmetrical alkenes 105 H4 Electrophilic addition to unsymmetrical alkenes 112 H5 Carbocation stabilization 115 H6 Reduction and oxidation of alkenes 117 H7 Hydroboration of alkenes 121 H8 Electrophilic additions to alkynes 124 H9 Reduction of alkynes 127 H10 Alkylation of terminal alkynes 129 H11 Conjugated dienes 131 Section I – Aromatic chemistry 135 I1 Aromaticity 135 I2 Preparation and properties 137 I3 Electrophilic substitutions of benzene 139 I4 Synthesis of mono-substituted benzenes 147 I5 Electrophilic substitutions of mono-substituted aromatic rings 150 I6 Synthesis of di- and tri-substituted benzenes 160 I7 Oxidation and reduction 164 Section J – Aldehydes and ketones 167 J1 Preparation 167 J2 Properties 169 J3 Nucleophilic addition 173 J4 Nucleophilic addition – charged nucleophiles 175 J5 Electronic and steric effects 181 J6 Nucleophilic addition – nitrogen nucleophiles 184 J7 Nucleophilic addition – oxygen and sulfur nucleophiles 187 J8 Reactions of enolate ions 191 J9 α-Halogenation 198 J10 Reduction and oxidation 200 J11 α,β-Unsaturated aldehydes and ketones 202 Section K – Carboxylic acids and carboxylic acid derivatives 205 K1 Structure and properties 205 K2 Nucleophilic substitution 209 K3 Reactivity 213 K4 Preparations of carboxylic acids 217 K5 Preparations of carboxylic acid derivatives 219 K6 Reactions 224 K7 Enolate reactions 234 Section L – Alkyl halides 239 L1 Preparation and physical properties of alkyl halides 239 L2 Nucleophilic substitution 242 L3 Factors affecting SN2 versus SN1 reactions 247 L4 Elimination 252 L5 Elimination versus substitution 256 L6 Reactions of alkyl halides 258 L7 Organometallic reactions 261 vi Contents