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Q. A compound $'A'$ having the molecular formula $C+{5}H_{12}O$, on oxidation gives a compound $'B'$ with molecular formula $C_{5}H_{10}O$. Compound $'B'$ gave a $2,4-$dinitrophenylhydrazine derivative but did not answer haloform test or silver mirror test. The structure of compound $'A'$ is

Aldehydes Ketones and Carboxylic Acids

Solution:

image
Since $(B)$ on reaction with $2,4-DNP$ forms a derivative, it implies that $(B)$ has imagegroup
$(B)$ gives $-ve$ Tollens’ test, hence it is not an aldehyde, but it is a ketone.
$ (B)$ gives $-ve$ haloform test, thus it is not a methyl ketone.
$ (B)$ is formed from the oxidation of $(A)$, thus $(A)$ is a $2^\circ$ alcohol, and among the given options,
$(A)$ is : image
and $\therefore (B)$ is image