Question

Which of the following arylamines will not form a diazonium salt on reaction with sodium nitrite in hydrochloric acid?

• A. m-Ethylaniline
• B. p-Aminoacetophenone
• C. $4$-Chloro-$2$-nitroaniline
• D. N-Ethyl-$2$-methylaniline

Answer 1

Answer: (C), (D)

The correct options are
C $4$-Chloro-$2$-nitroaniline
D N-Ethyl-$2$-methylaniline

$\begin{array}{c}Na{NO}_{2}HCl\\ ⟶\end{array}$ X No reaction

Due to presence of $N{O}_2$ group and $Cl$ atom at the $2$ and $4$ position. $4-Chloro-2-nitroaniline$ does not under go reaction with $NaN{O}_2$ and $HCl$

Also a secondary amine can not form diazonium salt.