JEE Main 2021 · 24 Feb · Shift 1 · Chemistry Q46

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ChemistrySingle correct+4 / -1Question 46 of 90

In the following reaction the reason why meta-nitro product also formed is :

Aniline with conc. HNO $_3$ / conc. H $_2$ SO $_4$ at 288 K gives p-nitroaniline [A] 51%, m-nitroaniline [B] 47% and o-nitroaniline [C] 2%.

Nitration of aniline with conc. HNO3 and conc. H2SO4 at 288 K: p-nitroaniline 51%, m-nitroaniline 47%, o-nitroaniline 2%.

-\mathrm{NH_2}

group is highly meta-directive

-\mathrm{NO_2}

substitution always takes place at meta-position

Formation of anilinium ion

low temperature

Answer and worked solution

Official answer: C

Anilinium ion. In strong acid much of the aniline is protonated to $\mathrm{C_6H_5NH_3^+}$ , a meta-directing deactivating group, which gives the large meta fraction.

(C)

Topics:Amines Aromatic hydrocarbons and electrophilic substitution

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JEE Main 2021 · 24 Feb · Shift 1, Chemistry question 46