The amine shown is treated with (i) NaNO2/HCl at 273-278 K, (ii) CuCN, (iii) H3O+ with heating. The final organic product gives effervescence with aqueous NaHCO3. Which structure is it?

JEE Advanced levelSingle correct optionDifficulty 3 of 3si275

The amine shown is treated with (i) $NaNO X_{2}$ /HCl at 273-278 K, (ii) $CuCN$ , (iii) $H X_{3} O X^{+}$ with heating. The final organic product gives effervescence with aqueous $NaHCO X_{3}$ . Which structure is it?

The amine shown is aniline. Diazotisation gives benzenediazonium chloride; the Sandmeyer reaction with

CuCN

gives benzonitrile (A); acid hydrolysis passes through benzamide (C) to benzoic acid (B), which alone liberates

CO X_{2}

from bicarbonate. Phenol (D) would form with water instead of CuCN.