Question

Chlorophenylmethane is treated with ethanolic NaCN and the product obtained is reduced with H\(_2\) in the presence of finely divided nickel to give:

• A. Phenylmethanamine
• B. 1-phenylethanamine
• C. 2-phenylethanamine
• D. 1-methyl-2-phenylethanamine
• E. phenylmethanamine

Hint:

In nucleophilic substitution reactions, halogen atoms (such as Cl) are often replaced by groups like \({CN}\) when treated with NaCN. Reduction of nitriles with hydrogen in the presence of a catalyst, such as Ni, leads to the formation of amines.

Answer 1

The Correct Option is C

Step 1: Chlorophenylmethane, also known as 1-chloromethylbenzene, undergoes a nucleophilic substitution reaction with NaCN in ethanolic solution to form a product where the chlorine atom is replaced by a cyano group (CN). This reaction produces the intermediate product, \({C}_6{H}_5{CH}_2{CN}\) (benzyl cyanide). \[ {C}_6{H}_5{CH}_2{Cl} + {NaCN} \rightarrow {C}_6{H}_5{CH}_2{CN} \] Step 2: The benzyl cyanide product is then subjected to catalytic hydrogenation in the presence of finely divided nickel, which reduces the cyano group (\(-{CN}\)) to a primary amine group (\(-{NH}_2\)). This results in the formation of \({C}_6{H}_5{CH}_2{NH}_2\), which is 2-phenylethanamine. \[ {C}_6{H}_5{CH}_2{CN} + H_2 \xrightarrow{{Ni}} {C}_6{H}_5{CH}_2{NH}_2 \] Thus, the final product is 2-phenylethanamine.