An organic compound $X$ is oxidized by using acidified $K_{2} C r_{2} O_{7}$ . The product obtained reacts with phenyl hydrazine, but does not answer silver mirror test. The possible structure of $X$ is:

C H_{3} C H_{2} O H

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(C H_{3})_{2} C H O H

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C H_{3} C O C H_{3}

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C H_{3} C H O

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Solution

The correct option is B $(C H_{3})_{2} C H O H$
The oxidation product of $X$ reacts with phenyl hydrazine, thus it contains $> C = O$ group. The same product does not give silver mirror test. Thus, it is a ketone, because only aldehydes gives silver mirror test.
Thus, the compound $X$ must be $2^{\circ}$ alcohol, as only secondary alcohols give ketones on oxidation and hence, $X$ is $(C H_{3})_{2} C H O H$ .

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