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Q: Give the reason for regioselectivity of nitration of acetinilide?
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Aromatic amines cannot be nitrated directly because they give unexpected oxidation products along with nitration products. This is because, HNO3 is not only a nitrating agent but also acts as a strong oxidizing agent. Therefore, to solve this problem, nitration is carried out by protecting the -NH2 group by acetylation. The acetyl group is finally removed by hydrolysis to give a mixture of o- and p-nitro amines.


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