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Question

An organic compounds of molecular formula C3H5O did not give a silver mirror with Tollens' reagent but gave an oxime with hydroxylamine, it may be

A
CHCHCH2OH
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B
CH3COCH3
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C
CH3CH2CHO
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D
CH2=CHOCH3
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Solution

The correct option is B CH3COCH3
The compound is a ketone, not an aldehyde because aldehydes give silver mirror test with Tollens' reagent. Alcohol/ethers do not form oxime with hydroxylamine. Ketones react with hydroxylamine to form oxime, but they don't give silver mirror with tollens' reagent.
RCHO+2[Ag(NH3)2]++3OHRCOO + 2Ag + 2H2O+4NH3Aldehyde Tollen's Reagent Carboxylate ion Silver mirror
Hence, the option (b) is the correct answer.

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