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Question

Compound ′A′ (molecular formula C3H8O) is treated with acidified potassium dichromate to form a product ′B′ (molecular formula C3H6O). ′B′ forms a shining silver mirror on warming with ammoniacal silver nitrate. ′B′ when treated with an aqueous solution of NH2CONHNH2, HCl and sodium acetate gives a product ′C′. Identify the structure of ′C′.

A
CH3CH2CH=NNHCONH2
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B
CH3C|CH3=NNHCONH2
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C
CH3C|CH3=NCONHNH2
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D
CH3CH2CH=NCONHNH2
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Solution

The correct option is A CH3CH2CH=NNHCONH2
It is clear that A is alcohol. On treating with acidified potassium dichromate, it forms an aldehyde or a ketone. Now, B is an aldehyde as it gives silver mirror test. Hence B is propanaldehyde (CH3CH2CHO) .

CH3CH2CHO+NH2CONHNH2+HCl+CH3COONaCH3CH2CH=NNHCONH2(C)
Hence, C is CH3CH2CH=NNHCONH2

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