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Question
Write a short note on Ammonolysis.
Solution
When an alkyl or benzyl halide is allowed to react with an ethanolic solution of ammonia, it undergoes nucleophilic substitution reaction in which the halogen atom is replaced by an amino (−NH2) group. This process of cleavage of the carbon-halogen bond is known as ammonolysis.
Amine is obtained when this substituted ammonium salt is treated with a strong base such as sodium hydroxide.
\[\ce{R - \overset{+}{N}H3 \overset{-}{X} + NaOH -> \underset{Amine}{R - NH}_2 + H2O + NaX}\]
Though primary amine is produced as the major product, this process produces a mixture of primary, secondary and tertiary amines, and also a quaternary ammonium salt as shown.
\[\ce{\underset{(1^\circ)}{RN}H2 ->[RX] \underset{(2^\circ)}{R2N}H ->[RX] \underset{(3^\circ)}{R3}N ->[RX] \underset{ammonium salt}{\underset{Quaternary}{R4 \overset{+}{N}\overset{-}{X}}}}\]
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