1. Tardigrade
  2. Question
  3. Chemistry
  4. A compound (A) of molecular formula C7H8O is insoluble in water and dilute sodium bicarbonate but dissolves in dilute aqueous sodium hydroxide and gives a characteristic colour with aqueous FeCl3. On treatment with bromine water, it readily gives a precipitate of C7H5OBr3. Write down the structure of the compound (A).

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Q. A compound $(A)$ of molecular formula $C_7H_8O$ is insoluble in water and dilute sodium bicarbonate but dissolves in dilute aqueous sodium hydroxide and gives a characteristic colour with aqueous $FeCl_3$. On treatment with bromine water, it readily gives a precipitate of $C_7H_5OBr_3$. Write down the structure of the compound $(A)$.

Alcohols Phenols and Ethers

Solution:

(i) Since $A$ gives characteristic colour with aqueous $FeCl_3$ so it contains a phenolic group.
(ii) Since $A$ when treated with $Br_2$ forms $C_7H_5OBr_3$ $(ppt.)$ and considering the molecular formula of $A$, it is most likely to be cresol.
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(iii) Since A on bromination forms tribromo derivative so, it is m-cresol i.e. image
The reactions are :

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