JEE Main · 2022 · 28 Jun 2022 · Shift 2 · Compounds Containing Nitrogen

In the nitration of aniline with ${\mathrm{HNO}}_3/{\mathrm{H}}_2{\mathrm{SO}}_4$, the amino group is first protonated in the strongly acidic medium to form anilinium ion (${\mathrm{C}}_6{\mathrm{H}}_5{\mathrm{NH}}_3^{+}$). This protonated form is a meta-directing group (due to the positive charge), so m-nitroaniline is formed. However, some aniline remains unprotonated and gives o- and p-nitroaniline (since $-{\mathrm{NH}}_2$ is ortho/para directing). The predominant products are p-nitroaniline and m-nitroaniline. In this reaction, ${\mathrm{H}}_2{\mathrm{SO}}_4$ acts as the acid (protonating aniline), while ${\mathrm{HNO}}_3$ acts as a base accepting a proton to generate the nitronium ion (${\mathrm{NO}}_2^{+}$). Therefore, statements (B) and (D) are correct.