Compound X of the molecular formula $C_4{H}_6$  takes up one equivalent of hydrogen in the presence of Pt to form another compound Y which on oxidative ozonolysis gives only ethanoic acid. The compound X can be?

detailed solution

Correct option is D

[Step 1]: C4H6 + H2→Pt C4H8→Ozonolysis 2 CH3COOH          to get only ethanoic acid the alkene which undergoes ozonolysis must be 2–butene from the above reaction          [Step 2]: CH2=CH−CH=CH2 + H2→Pt CH3−CH=CH−CH3→Ozonolysis 2 CH3COOH          But–1,3–diene on mono hydrogenation will undergo 1,4–addition can form 2–butene, further ozonolysis of 2–butene will give only ethanoic acid           [Step 3]: CH3−C≡C−CH3+ H2→Pt CH3−CH=CH−CH3→Ozonolysis 2 CH3COOH          But–2–yne on mono hydrogenation will give 2–butene, further ozonolysis of 2–butene will give only ethanoic acid           [Step 4]: CH2=C=CH−CH3 + H2→Pt CH3−CH=CH−CH3→Ozonolysis 2 CH3COOH          But–1,2–diene on mono hydrogenation will undergo 1,2–addition can form 2–butene, further ozonolysis of 2–butene will give only ethanoic acid