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 :- [2015]
(a) 2-pentanone (b) 3-pentanone
(c) n-amyl alcohol (d) pentanal

Answer 1

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 :- [2015]

(a) 2-pentanone

(b) 3-pentanone

(c) n-amyl alcohol

(d) pentanal

Answer 2

The product is 3 pentanone.

Explanation:

• The reactant has the molecular formula of C5H10O.

• So it must be an aldehyde or a ketone, because it reacts with phenyl hydrazine.

• Now, its said that the reactant doesn't react with Tollen's reagent.

• Aldehydes react with Tollen's reagent which is ammoniacal silver nitrate to reduce to silver which gives silver mirror on the test tube.

• So as it gives negative result, so its not an aldehyde.

• Now, the reactant doesn't give Iodoform test.

• The secondary alcohol and ketones or Aldehydes with alpha methyl group gives Iodoform test to produce Iodoform.

• Now, as the reactant doesn't give Iodoform test, then we can conclude that the keto group isn't present on 2nd carbon.

• So its 3 pentanone.

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