[28.1] carbon-carbon bond formation
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how can nitriles be formed from haloalkanes?
• haloalkane + NaCl —> nitrile + NaCl • nucleophilic substitution mechanism
how can nitriles be formed form a carbonyl compound via a hydroxynitirle?
• aldehyde / ketone + HCN —> hydroxynitirle + OH- • nucleophilic addition mechanism
reduction of nitriles to form amines
• nitrile + 2H₂ —> primary amine • conditions = nickel catalyst
hydrolysis of nitriles to form a carboxylic acid
• nitrile + 2H₂O + HCl —> carboxylic acid • conditions = heat
forming C-C bonds to benzene rings: friedel-crafts alkylation
• benzene + haloalkane ➞ alkylbenzene + HX • conditions = AlCl₃
forming C-C bonds to benzene rings: friedel-crafts acylation
• benzene + acyl chloride —> phenyl ketone + HCl • conditions: AlCl₃