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An organic compound X having molecular formula C5H10OC_5H_{10}O yields phenyl hydrazone and gives a negative response to the iodoform test and Tollen's test. It produces n-pentane on reduction. X could be:

A

Pentanal

B

2-Pentanone

C

3-Pentanone

D

n-Amyl alcohol

Step-by-Step Solution

To identify compound X (C5H10OC_5H_{10}O):

  1. Phenylhydrazone Formation: The reaction with phenylhydrazine indicates the presence of a carbonyl group (>C=O>C=O). This confirms X is an aldehyde or ketone, eliminating the alcohol (Option D).
  2. Negative Tollen's Test: Tollen's reagent oxidizes aldehydes to carboxylic acids (silver mirror). A negative result indicates X is not an aldehyde, eliminating Pentanal (Option A). X must be a ketone.
  3. Negative Iodoform Test: The iodoform test detects the presence of a methyl ketone group (CH3C=OCH_3-C=O).
  • 2-Pentanone (CH3COCH2CH2CH3CH_3-CO-CH_2CH_2CH_3) contains this group and would give a positive test.
  • 3-Pentanone (CH3CH2COCH2CH3CH_3CH_2-CO-CH_2CH_3) does not contain a methyl group attached directly to the carbonyl carbon. It gives a negative test.
  1. Reduction: Reduction of 3-pentanone yields n-pentane, consistent with the problem statement.
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