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JEE Advanced levelSingle correct optionDifficulty 3 of 3nc036

Nitration of aniline with $HNO X_{3}$ and $H X_{2} SO X_{4}$ gives a considerable amount of 3-nitroaniline because:

Athe $NH X_{2}$ group is a meta director in the free base
B $H X_{2} SO X_{4}$ blocks the ortho and para positions as sulfonic acid groups
Cin the strongly acidic medium aniline is protonated to the anilinium ion, whose $- NH X_{3} X^{+}$ group is meta directing
Dnitric acid oxidises the ring to a meta-quinone

Answer: C

Aniline is a base, so in mixed acid a large fraction is converted into anilinium ion

C X_{6} H X_{5} NH X_{3} X^{+}

. The

- NH X_{3} X^{+}

group is strongly electron withdrawing and deactivating, so it directs the nitronium ion to the meta position. The free

NH X_{2}

is an ortho/para director.

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