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Question

An organic compound 'X' having molecular formula C5H10O yields phenyl hydrazone and gives negative response to the Iodoform test and Tollen's test. It produces n-pentane on reduction. 'X' could be:

A
3-pentanone
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B
n-amyl alcohol
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C
pentanal
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D
2-pentanone
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Solution

The correct option is A 3-pentanone
An organic compound 'X' having molecular formula C5H10O yields phenyl hydrazone. This indicates presence of carbonyl group.
It gives negative response to the Iodoform test. It indicates absence of methyl keto group.
Hence, n-amyl alcohol and 2-pentanone are ruled out.
It gives negative response to the Tollen's test. It indicates absence of aldehyde group.
Hence, pentanal is ruled out.
It produces n-pentane on reduction. This indicates presence of 5-carbon backbone.
'X' could be 3-pentanone.

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