Question:

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 $(A)$.

Updated On: Jul 5, 2022
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The Correct Option is D

Solution and Explanation

(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. The reactions are :
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Concepts Used:

Alcohols, Phenols, and Ethers

Alcohol is formed when a saturated carbon atom bonds to a hydroxyl (-OH) group. It is an organic compound that contains a hydroxyl functional group attached to a carbon atom.

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Ether is formed when oxygen atom bonds to two alkyl or aryl groups. It is an organic compound that has an oxygen atom that is connected to two aryl and alkyl groups.

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