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Question

Aniline when acetylated, the product on nitration followed by alkaline hydrolysis gives:

A
o-Nitroacetanilide
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B
p-Nitroaniline
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C
m-Nitroaniline
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D
Acetanilide
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Solution

The correct option is B p-Nitroaniline

Acetanilide on nitration followed by alkaline hydrolysis :

It occurs under the presence of H2SO4 and HNO3

Aniline is highly, ring activating so it forms both o- and p- products. But, on acetylation of NH2forms acetanilide that deactivates the N as it diverts the lone pair in through cross conjugation.

Thus, we get p-nitroaniline.

Option B is correct.


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