Question Details

Reaction of aniline with conc. HNO3 and conc. H2SO4 at 298 K will produce 47% of

Options

A

p-Nitroaniline

B

o-Nitroaniline

C

m-Nitroaniline

D

2,4-Dinitroaniline

Show Answer

Correct Answer :

Option A

p-Nitroaniline

Solution :

The correct option is p-Nitroaniline.

Explanation:
When aniline is treated with a nitrating mixture containing concentrated nitric acid (conc. HNO3) and concentrated sulfuric acid (conc. HS2O4) at 298 K, it undergoes electrophilic aromatic substitution (nitration).

Under these strongly acidic conditions, a significant portion of aniline is protonated to form the anilinium ion:
C6H5-NH2+H+C6H5-NH3+
The positively charged -NH3+ group is electron-withdrawing and deactivating, directing the incoming nitronium ion electrophile (NO2+) to the meta-position.

At the same time, the unprotonated aniline remains highly reactive and directs substitution to the ortho and para positions due to the electron-donating resonance effect of the lone pair on the nitrogen atom.

As a result, a mixture of three isomeric nitroanilines is obtained in the following approximate yields:
1. p-Nitroaniline (para product)
2. m-Nitroaniline (meta product)
3. o-Nitroaniline (ortho product)

According to the reaction stoichiometry and standard experimental conditions, p-nitroaniline and m-nitroaniline form the bulk of the products, with p-nitroaniline designated as the correct option here.

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