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Question

In the reaction given below, step 1 and step 2 are respectively, Xstep−1−−−−→Ystep−2−−−−→Z
(X=C6H5NH2;Z=p−NO2C6H4NH2) :

A
nitration, acetylation
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B
nitration, sulphonation
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C
sulphonation, nitration
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D
acetylation, nitration
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Solution

The correct option is D acetylation, nitration
In step 1, aniline is acylated so that it protects the amino group and decreases the reactivity and hence, avoids trinitration.
PhNH2+CH3COClPhNHCOCH3
Now, the resulting compound can be easily nitrated without fear of trinitration.
PhNHCOCH3+HNO3/H2SO4pnitroaniline
Note that during nitration, the COCH3 group is hydrolysed back to the amino group.
So, option D is the correct answer.

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