Question

$N$, $N$-Dimethylaniline is treated with aqueous $NaNO_2/HCl$, the product formed is

• A. $p$-($N$, $N$-dimethylamino)benzenediazonium chloride
• B. $p$-($N$, $N$-dimethylamino)phenol
• C. $p$-nitroso-$N$, $N$-dimethylaniline
• D. $p$-nitro-$N$, $N$-dimethylaniline

Answer 1

Answer: (C)

In tertiary aromatic amines, there is no $N - H$ bond. Therefore, nitrosoation on Nitrogen atom and salt formation is not possible, instead the aromatic ring is nitrosoated at the para position forming a p-nitroso derivative. This derivative on reaction with alkali gives parrot green colouration.