Question

An organic compound 'X' having molecular formula C4H8O gives orange-red ppt. with 2, 4-DNP reagent. It does not reduce tollens' reagent but gives yellow ppt. of iodoform on heating with NaOI. Compound X on reduction with LiAIH4 gives compound 'Y' which undergoes dehydration reaction on heating with conc. H2SO4 to form But-2-ene. Identify the compounds X and Y.

Answer 1

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Answer 2

Hey dear,

● Answers -
Compound X => Butan-2-one
Compound Y => Butan-2-ol

● Explanation -
Molecular formula C4H8O indicates X being either aldehyde or ketone.

As X doesn't reduce Tollen's reagent, it must be a ketone.

Postive iodoform test indicates methyl group at one end of ketone X.

Then compound X must be CH3-CO-C2H5 i.e. butan-2-one.

Butan-2-one (X) on reduction with LiAlH4 gives butan-2-ol (Y).
CH3-CO-C2H5 ---> CH3-CH(OH)-C2H5

Butan-2-ol (Y) on hydrolysis with conc.H2SO4 gives but-2-ene.
CH3-CH(OH)-C2H5 ---> CH3-CH=CH-CH3

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