Q23 / 180 · KCET 2019 · Chemistry

If Aniline is treated with \( 1: 1 \) mixture of conc. \( \mathrm{HNO}_{3} \) and con. \( \mathrm{H} 2 \mathrm{SO}_{4}, \mathrm{p} \)-nitroaniline and \( \mathrm{m} \) -
nitroaniline are formed nearly in equal amounts. This is due to

  • A
    \( \mathrm{m} \& \mathrm{p} \) directing property of \( -\mathrm{NH}_{2} \) group.
  • B
    isomerization of some p-nitroaniline into m-nitroaniline.
  • C
    m-directing property of \( -\mathrm{NH}_{2} \) group.
  • Correct answer
    D
    protonation of \( -\mathrm{NH}_{2} \) which causes deactivation of benzene ring.

Solution

(D)
In presence of acid aniline gets protonated to anilinium ion which is meta directing.

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

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