Question

What is the product when $C_{6}H_{5}-CH_{2}-NH_{2}$ reacts with nitrous acid?

• A. $C_{6}H_{5}-N\equiv N$
• B. $C_{6}H_{5}-CH_{2}-\overset{\oplus}{N}\equiv N$
• C. $C_{6}H_{5}-CH_{2}-OH$
• D. $C_{6}H_{5}-NH_{2}$

Answer 1

Answer: (C)

Primary amines with nitrous acid undergo diazotisation producing diazonium salt which further dissociates to alcohol and dinitrogen.

$C_{6}H_{5}-CH_{2}-NH_{2}\overset{H N O_{2}}{ \rightarrow }\left[C_{6} H_{5} C H_{2} \overset{+}{N_{2}}\right] \rightarrow C_{6}H_{5}-CH_{2}-OH$