1.

A compound A(C_(7)H_(5)N) on hydrolysis with strong aqueous acid gives another compound B which is a monobasic aromatic carboxylic acid. The compound B on treatment with ammonia gives a salt which on heating gives C. The compound C undergoes Hofmann/s bromamide reaction to yield aniline. name A,B andC and write the chemical reactions involved.

Answer»

Solution :(i) SINCE COMPOUND `A(C_(7)H_(5)N)` on hydrolysis with strong aqueous ACID gives compound B which is a monobasic aromatic acid, therefore, compound (A) must be benzonitrile and compound (B) must be benzoic acid.
`underset("Benonitrile (A) "M.F.C_(7)H_(5)N)(C_(6)H_(5)CN)+2H_(2)O+H^(+)to underset("Benzoic acid (B)")(C_(6)H_(5)COOH)+NH_(4)^(+)`
(ii) Since compound B on treatment with ammonia gives a salt which on heating gives C, therefore, the salt must be AMMONIUM benzoate and the compound C must be benzamide.
`underset("Benzoic acid (B)")(C_(6)H_(5)COOH) overset(NH_(3))to underset("Amm. benzoate")(C_(6)H_(5)COONH_(4)) underset(-H_(2)O)overset(Delta)to underset("Benzamide (C)")(C_(6)H_(5)CONH_(2))`
(iii) The fact that compound (C) is benzamide is confirmed by the fact that it on Hofmann mromamide reaction gives aniline.
`underset("BEnzamide (C)")(C_(6)H_(5)CONH_(2)) underset(("Hofmann bromamide reaction"))overset(Br_(2)-NAOH)to underset("Aniline")(C_(6)H_(5)NH_(2))`


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