Q9 / 180 · COMEDK 2026 (9 May Shift 2) · Chemistry

Identify the final product formed when benzenamine reacts with the given reagents in the sequential order as:
i. (CH$_3$$-$CO )$_2$O / Pyridine.
ii. Conc. HNO$_3$ + H$_2$SO$_4$ & then reacted with H$_3$O$^+$
iii. NaNO$_2$ HCl (273K) & then reacted with H$_3$PO$_2$(aq).

  • A
    2- Chloro- 4-Nitrophenol
  • B
    4 – Chloro– 2 – Nitroaniline
  • C
    4–Nitrophenol
  • Correct answer
    D
    Nitrobenzene

Solution

Benzenamine (aniline) reacts with acetic anhydride in the presence of pyridine to form acetanilide. This step protects the amino group and prevents polysubstitution and oxidation.

Acetanilide undergoes nitration with a mixture of concentrated $\text{HNO}_3$ and concentrated $\text{H}_2\text{SO}_4$ to form $p$-nitroacetanilide as the major product due to steric hindrance at the ortho position.

Hydrolysis of $p$-nitroacetanilide with $\text{H}_3\text{O}^+$ removes the acetyl group, yielding $p$-nitroaniline.

$p$-Nitroaniline reacts with $\text{NaNO}_2$ and $\text{HCl}$ at $273\text{ K}$ to form $p$-nitrobenzenediazonium chloride.

Reaction of the diazonium salt with aqueous $\text{H}_3\text{PO}_2$ (hypophosphorous acid) reduces the diazonium group, replacing it with a hydrogen atom (deamination).

The final product formed is nitrobenzene.

Answer: Nitrobenzene

Hence, the correct answer is option: 'D'.

Relevant Questions