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
b
c
d
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 functional group. But only aldehydes give siler mirror test with ammonical AgNO3.Aldehyde without a- hydrogen atom reacts with concentrated NaOH to give alcohol an d sodium salt of carboxylic acid, according to Cannizzaro reaction, and only O-substituted aldehyde undergoes oxidation to give 1,2-substituted carboxylic acid. The sequence of reaction are as follows.
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