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Question

An organic compound X with molecular formula C5H10O gives test with phenyl hydrazine but gives a negative response to iodoform test and Tollen’s test. It produces n-pentane on reduction. The compound could be

A
pentanal
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B
pentan-2-one
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C
pentan-3-one
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D
amyl alcohol
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Solution

The correct option is C pentan-3-one
O CH3CH2CCH2CH3
This compound lacks CH3CO or CH3CH(OH) group hence gives negative Iodoform test. It is a ketone hence gives negative Tollen’s test. It contain 5C hence gives n-pentane upon reduction.

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