Question

A compound $(A)$ of molecular formula $C_7{H}_{8}O$ is insoluble in water and dilute sodium bicarbonate but dissolves in dilute aqueous sodium hydroxide and gives a characteristic colour with aqueous $FeC{l}_3$. On treatment with bromine water, it readily gives a precipitate of $C_7{H}_{5}OB{r}_3$. Write down the structure of the compound $(A)$.

• A.
• B.
• C.
• D.

Answer 1

Answer: (D)

(i) Since $A$ gives characteristic colour with aqueous $FeC{l}_3$ so it contains a phenolic group.
(ii) Since $A$ when treated with $B{r}_2$ forms $C_7{H}_{5}OB{r}_3$ $(ppt.)$ and considering the molecular formula of $A$, it is most likely to be cresol.

(iii) Since A on bromination forms tribromo derivative so, it is m-cresol i.e.
The reactions are :