A mixture of two aromatic compounds (A) and (B) separated by dissolving it in chloroform followed by extraction with aqueous ` KOH` solution. The organic layer containing compound (A) when heated with alcoholic solution of ` KOH` produced a compound (C ) `( C_7 H_5 N)` associated with an unpleasant odour . The alkaline aqueous layer on the other hand , when heated with chloroform and then acidified gave a mixture of two isometic compounds (D) and (E ) of molecular formula ` C_7 H_6O_2`. Identity the compounds (A), (B ) . (C ) (D), and (E ) and write their structures .

Answer

A

Explanation

(i) Given mixture of (A) and (B) `overset(CHCl_(2))underset(+KOH(Aq))tounderset("(A)")("Organic layer")+underset("(B)")("Alkalineaquous layer")`
(ii) Organic layer on treating with KOH (alc.) producer (C) of unpleasant odour `(C_(2)H_(3)N)` and thus(C) is `C_(6)H_(3)NC.` this carbylamines reaction.Therefore, (A) is `C_(5)H_(5)NH_(2)`.
`underset("Aniline")(C_(6)H_(5)NH_(2))+CHCl_(3)+3KOH(aq)to underset("(C)")(C_(6)H_(5)NC)+3KCl+3H_(2)O`
(iii) Alkaline layer on treating with `CHCl_(3)` followed with acidification gives two isomers (D) and (E) `(C_(2)H_(6)O_(2))`
This is Riemer -teimann's reaction and thus, (B) is `C_(6)H_(5)OH`.