Q9 of 26 Page 1

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 LiAlH4 gives compound ‘Y’ which undergoes dehydration reaction on heating with conc. H2SO4 to form But-2-ene. Identify the compounds X and Y.

Since, X gives orange-red ppt. with 2,4-DNP reagent but it does not reduce Tollens’ reagent so it is a ketone. The ketone is a methyl ketone because it gives iodoform test. So, the ketone can be 2- butanone. This on reduction with LiAlH4 gives 2- butanol i.e. compound Y. This undergoes dehydration reaction on heating with conc. H2SO4 to form But-2-ene.


In the presence of LiAlH4



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