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An organic compound 'X' having molecular formula $C_5H_{10}O$ yields phenyl hydrazone and gives negative response to the Iodoform test and Tollens' test. It produces n-pentane on reduction. 'X' could be:
A
pentanal
B
2-pentanone
C
3-pentanone
D
n-amyl alcohol
Detailed Solution
Forms a phenylhydrazone, so X is a carbonyl compound.
Negative Tollens' test, so it is a ketone, not an aldehyde.
Negative iodoform test, so it has no $CH_3CO-$ group.
Reduction gives n-pentane, so the chain is unbranched: X is 3-pentanone, $CH_3CH_2COCH_2CH_3$.
$CH_3CH_2COCH_2CH_3 \xrightarrow{Zn-Hg/HCl} CH_3CH_2CH_2CH_2CH_3$
Negative Tollens' test, so it is a ketone, not an aldehyde.
Negative iodoform test, so it has no $CH_3CO-$ group.
Reduction gives n-pentane, so the chain is unbranched: X is 3-pentanone, $CH_3CH_2COCH_2CH_3$.
$CH_3CH_2COCH_2CH_3 \xrightarrow{Zn-Hg/HCl} CH_3CH_2CH_2CH_2CH_3$