Question

What is the major product of the following sequence of reaction?
$PhC{H}_{2}Cl\stackrel{NaCN}{⟶}\stackrel{LiAl{H}_4}{⟶}\stackrel{(C{H}_{3}CO{)}_{2}O}{⟶}$

• A. $PhC{H}_{2}C{H}_{2}N{H}_2$
• B. $PhC{H}_{2}C{H}_{2}CONHC{H}_3$
• C. $PhC{H}_{2}C{H}_{2}ONHCOC{H}_3$
• D. $PhC{H}_{2}C{H}_{2}NHCOC{H}_3$

Answer 1

The correct option is D $PhC{H}_{2}C{H}_{2}NHCOC{H}_3$

Reaction:
$PhC{H}_{2}Cl\stackrel{NaCN}{⟶}PhC{H}_{2}CN\stackrel{LiAl{H}_4}{⟶}PhC{H}_{2}C{H}_{2}N{H}_2\stackrel{(C{H}_{3}CO{)}_{2}O}{⟶}PhC{H}_{2}C{H}_{2}NH-COC{H}_3$

In first step nucleophilic substitution the chlorine is replaced by $CN$ and then reduction to give amines and final step is $N-acylation$.

Option D is correct.