19.1 + 19.2 Amines and Nitriles

Question 1

Production of amines
Nucleophilic substitution of halogenoalkanes when they are heated under pressure with NH3 in ethanol

Answer 1

• Halogenoalkane + NH3 in ethanol (heat/pressure) = Amine + HX

Question 2

Production of nitriles

Answer 2

Reaction of a halogenoalkane with KCN with ethanol and heat under reflux
(Nucleophilic substitution)

• Halogenoalkane + KCN (ethanol) + heat = Nitrile + KX

Question 3

Mechanism for nucleophilic substitution

Answer 3

in notes

Question 4

Hydroxynitriles

Answer 4

Hydroxynitrile- contains OH and CN group, typically attached to the same carbon

Question 5

Production of hydroxynitriles

Answer 5

Reaction of aldehydes/ketones with HCN, KCN as a catalyst, and heat
- 2 steps: nucleophilic attack and then protonation
- drawings in notes

Question 6

Hydrolysis of nitriles

Answer 6

• by either dilute acid or alkali, followed by acidification to produce a carboxylic acid
  1) Nitrile + HCI + 2H20= carboxylic acid + ammonium chloride salt
  2) Nitrile + NaOH + H20 = sodium carboxylate + ammonia
  *sodium carboxylate is acidified to produce carboxylic acid