The percentage of carbon, hydrogen, and nitrogen in an disibstituted aromatic compound `(A)` is `71.11, 6.67`, and `10.34`, respectively. It molecule contains a single atom of nitrogen. Compound `(A)` evolves `NH_3` when heated with `NaOH` to form a salt `(B)` from which an acid `(C)` is obtained on acidification. If an electrophilic substitution is carried on `(C)`, a leaving electrophile can occupy either of the two identical positions available in the ring. Acid `(C)` on heating with `PCl_5` gives `(D)` which reacts with `(B)` to give an organic product `(E)`. Give the structures of `(A)` to `(E)` with proper reasoning.

Explanation

(i) `{:(,"Simplest ratio"),("C=71.1 %,"(71.11)/(12)=5.92,(5.92)/(0.74)=8),("H= 6.67 %,"(6.67)/(1)=6.67,(6.67)/(0.74)=9),("N=10.37 %,"(10.37)/(14)=0.74,(0.74)/(0.74)=1),("O=11.85%,"(11.85)/(16)=0.74,(0.74)/(0.74)=1):}`
The empiricial formula of `(A) = C_8 H_9 NO`
`A rArr` contains only one `N` atom in its molecule and thus the molecular formula of `(A) = C_8 H_9 NO`.
(ii) `(-overset(O)overset(||)(C)-NH_(2))`
(iii)
(iv)
(v) `SE` reaction on `(C)` gives one product and thus `(C)` is para derivative and `(A)` and `(B)` are para derivatives.
Reactions :