[28.1] carbon-carbon bond formation

Question 1

how can nitriles be formed from haloalkanes?

Answer 1

• haloalkane + NaCl —> nitrile + NaCl
• nucleophilic substitution mechanism

Question 2

how can nitriles be formed form a carbonyl compound via a hydroxynitirle?

Answer 2

• aldehyde / ketone + HCN —> hydroxynitirle + OH-
• nucleophilic addition mechanism

Question 3

reduction of nitriles to form amines

Answer 3

• nitrile + 2H₂ —> primary amine
• conditions = nickel catalyst

Question 4

hydrolysis of nitriles to form a carboxylic acid

Answer 4

• nitrile + 2H₂O + HCl —> carboxylic acid
• conditions = heat

Question 5

forming C-C bonds to benzene rings: friedel-crafts alkylation

Answer 5

• benzene + haloalkane —> alkylbenzene + HX
• conditions = AlCl₃

Question 6

forming C-C bonds to benzene rings: friedel-crafts acylation

Answer 6

• benzene + acyl chloride —> phenyl ketone + HCl
• conditions: AlCl₃