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Q.

A hydrocarbon 'X' with formula C5H8 uses two moles of H2 on catalytic hydrogenation of its one mole. On ozonolysis, 'X' yields two moles of methane dicarbaldehyde. The hydrocarbon  X is:

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a

hexa-1,3,5 - triene

b

cyclohexa- 1,4 - diene

c

cyclohexa- 1,3 - diene

d

1 - methylcyclopenta-1,4- diene

answer is D.

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Detailed Solution

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Explanation:

Let’s analyze the given information:

  • The formula of the hydrocarbon is \( C_5H_8 \), indicating a degree of unsaturation of 2.
  • On catalytic hydrogenation, it uses two moles of \( H_2 \), which suggests the presence of two double bonds (alkene) or one triple bond (alkyne).
  • On ozonolysis, the hydrocarbon yields two moles of methane dicarbaldehyde (\( OHC-CH_2-CHO \)).

This indicates the hydrocarbon is likely an alkyne (as triple bonds can cleave into aldehydes upon ozonolysis).

The Hydrocarbon \( X \):

The hydrocarbon \( X \) is penta-1,4-diyne, with the structure:

HC≡C-CH₂-C≡CH

On hydrogenation, both triple bonds are reduced to single bonds.

On ozonolysis, both triple bonds are cleaved, forming two moles of methane dicarbaldehyde.

Answer: d

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