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Question

A compound A has molecular formula C7H7NO. On treatment with Br2 and KOH, A gives an amine B which gives carbylamine test. B upon diazotization and coupling with phenol gives an azo dye. A can be:
  1. C6H5CONH2
  2. C6H5NO2
  3. C6H5CONHCOCH3
  4. o,m or p-C6H4(NH2)CHO

A
C6H5NO2
B
C6H5CONHCOCH3
C
C6H5CONH2
D
o,m or p-C6H4(NH2)CHO
Solution
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According to the reactions given for compound B, B should be aniline as it gives carbylamine test and also couples with phenol to form dye.

The action of Br2 and KOH is Hoffmann bromamide reaction in which aniline is formed.

Therefore, A should be an amide.

Thus, A is C6H5CONH2.

Option B is correct.

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