Q.

An organic compound on reaction with 2,4-dinitrophenylhydrazine (2,4-DNP) gives a yellow precipitate. It also gives silver mirror on reaction with ammonical AgNO3. It gives an alcohol and sodium salt of a carboxylic acid on reaction with concentrated NaOH. It yields benzene-1, 2-dicarboxylic acid on heating with alkaline KMnO4. The structure of the compound among the following is

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a

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b

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c

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d

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answer is C.

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Detailed Solution

The compound gives positive (2,4-DNP) test indicating it contains either an aldehydic or ketonic functions group. But only aldehydes give silver mirror test with ammonical AgNO3 Aldehyde without a-hydrogen atom reacts with  concentrated NaOH to give alcohol and sodium salt of carboxylic acid, according to Cannizaro reaction, and only O-substituted aldehyde undergoes oxidation to give disubstituted carboxylic acid. The sequence of reaction are as follows.

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An organic compound on reaction with 2,4-dinitrophenylhydrazine (2,4-DNP) gives a yellow precipitate. It also gives silver mirror on reaction with ammonical AgNO3. It gives an alcohol and sodium salt of a carboxylic acid on reaction with concentrated NaOH. It yields benzene-1, 2-dicarboxylic acid on heating with alkaline KMnO4. The structure of the compound among the following is