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Q.

Compound X of the molecular formula C4H6  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?

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a

CH2=CH−CH=CH2

b

CH3−C≡C−CH3

c

CH2=C=CH−CH3

d

All

answer is D.

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Detailed Solution

[Step 1]: C4H6 + H2Pt C4H8Ozonolysis 2 CH3COOH

          to get only ethanoic acid the alkene which undergoes ozonolysis must be 2–butene from the above reaction

          [Step 2]: CH2=CHCH=CH2 + H2Pt CH3CH=CHCH3Ozonolysis 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]: CH3CCCH3+ H2Pt CH3CH=CHCH3Ozonolysis 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=CHCH3 + H2Pt CH3CH=CHCH3Ozonolysis 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 

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