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Two isomeric organic compounds X and Y of molecular formula C4H6 gave following reactions.(i)   Both discharged colour of Br2 in CCl4(ii)   X gives a precipitate with ammonical AgNO3(iii)  Y does not give ppt with ammonical AgNO3 and on oxidation gives oxalic acid and CO2Hence X and Y are respectively

Question

Two isomeric organic compounds X and Y of molecular formula C4H6 gave following reactions.(i)   Both discharged colour of Br2 in CCl4(ii)   X gives a precipitate with ammonical AgNO3(iii)  Y does not give ppt with ammonical AgNO3 and on oxidation gives oxalic acid and CO2Hence X and Y are respectively

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Solution

The two isomeric organic compounds X and Y of molecular formula C4H6 are likely to be but-1-yne and but-2-yne respectively.

Here's why:

(i) Both X and Y discharge the colour of Br2 in CCl4. This indicates that both compounds contain a carbon-carbon triple bond, which reacts with bromine to form a dibromo derivative, decolourising the bromine.

(ii) X gives a precipitate with ammonical AgNO3. This suggests that X has a terminal alkyne group (C≡CH), which can react with ammonical silver nitrate to form a white precipitate of silver acetylide.

(iii) Y does not give a precipitate with ammonical AgNO3, suggesting it does not have a terminal alkyne group. On oxidation, Y gives oxalic acid and CO2. This suggests that Y has an internal alkyne group (C≡C), which on oxidation gives a dicarboxylic acid (oxalic acid) and carbon dioxide.

Therefore, X is but-1-yne (which has a terminal alkyne group) and Y is but-2-yne (which has an internal alkyne group).

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