When the amide reacts with LiAlH 4 , it reduces to amine and carboxylic acid reduced to alcohol by LiAlH 4 . Acidic medium breaks the peptide linkage and EtOH gives the esterification reaction with carboxylic acid. HNO 2 converts the primary amine into alcohol. Base will take the acidic proton But the amine nitrogen is better nucleophile and gives the acetylation reaction with CH 3 COCl . Base will take the acidic proton and carbanion is formed. But the amine nitrogen is better nucleophile and gives the nucleophilic substitution reaction with Ph - CH 2 - Cl .

In the first reaction, the base will take the acidic proton, then the nitrogen will attack on benzene ring. After that, the nitrogen lone pair will give the substitution reaction by ArS N 2 Mechanism because the nitrogen is better nucleophile. Step 1 : In second step, there is hydrolysis of dipeptide bond occurs. The peptide bond breaks into the two compounds by hydrolysis. Step 2 :