An aromatic compound ‘A’ on treatment with aqueous ammonia and heating forms compound ‘B’

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asked Dec 27, 2017 in Chemistry by sforrest072 (157,439 points) 61 410 942

An aromatic compound ‘A’ on treatment with aqueous ammonia and heating forms compound ‘B’ which on heating with Br2 and KOH forms a compound ‘C’ of molecular formula C6H7N. Write the structures and IUPAC names of compounds A, B and C.

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answered Dec 27, 2017 by mdsamim (213,225 points) 5 10 15
selected Dec 27, 2017 by sforrest072
 
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It is given that compound ‘C’ having the molecular formula, C6H7N is formed by heating
compound ‘B’ with Br2 and KOH. This is a Hoffmann bromamide degradation reaction.
Therefore, compound ‘B’ is an amide and compound ‘C’ is an amine. The only amine having the molecular formula, C6H7N is aniline, (C6H5NH2).

Therefore, compound ‘B’ (from which ’C’ is formed) must be benzamide, (C6H5CONH2).

Further, benzamide is formed by heating compound ‘A’ with aqueous ammonia. Therefore, compound ‘A’ must be benzoic acid.

The given reactions can be explained with the help of the following equations:

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