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JEE Main levelSingle correct optionDifficulty 2 of 3nc099

Direct nitration of aniline with conc. $HNO X_{3}$ and conc. $H X_{2} SO X_{4}$ gives a significant amount of 3-nitroaniline because

Ain the strongly acidic medium aniline is protonated, and the anilinium ion $C X_{6} H X_{5} NH X_{3} X^{+}$ is meta-directing
Bthe $NH X_{2}$ group is itself meta-directing
Cnitronium ion attacks the nitrogen to give an N-nitro compound
Dsulfuric acid sulfonates the ring at the meta position

Answer: A

In the nitrating mixture a large fraction of aniline is converted to the anilinium ion, whose

- NH X_{3} X^{+}

group is electron-withdrawing and directs meta. The remaining free aniline gives the ortho/para products, so a mixture is formed.

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