Question:hard

Aniline on direct nitration yields

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Nitration is carried out in a strongly acidic medium (conc. \(HNO_3\) and \(H_2SO_4\)). In this medium aniline gets largely protonated to the anilinium ion \(C_6H_5NH_3^+\).
Updated On: Jun 16, 2026
  • 51%-ortho, 47%-para, 2%-meta derivatives
  • 51%-meta, 47%-ortho, 2%-para derivatives
  • 51%-para, 47%-meta, 2%-ortho derivatives
  • 51%-ortho, 47%-meta, 2%-para derivatives
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The Correct Option is B

Solution and Explanation

Step 1: Note the reaction conditions.
Nitration of aniline uses a strongly acidic mixture of concentrated \(HNO_3\) and \(H_2SO_4\). In this acid medium most of the aniline becomes protonated to the anilinium ion \(C_6H_5NH_3^+\).

Step 2: See how the directing nature changes.
The free \(-NH_2\) group is ortho/para directing and ring activating. But the protonated \(-NH_3^+\) group is positively charged, so it pulls electrons away and behaves as a meta directing, deactivating group.

Step 3: Realise both species are present.
A small amount of free aniline still reacts and sends the nitro group to ortho and para, while the protonated form sends it to meta. So we get a mixture from all three positions.

Step 4: Recall the observed product ratio.
Experimentally direct nitration of aniline gives about 51% ortho, 47% para and only about 2% meta derivatives.

Step 5: Conclude.
The product distribution is 51% ortho, 47% para, 2% meta.

\[ \boxed{51\%\ \text{ortho},\ 47\%\ \text{para},\ 2\%\ \text{meta}} \]
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