Compound X has the formula C8H14. X reacts with one molar equivalent of hydrogen in the presence of a palladium catalyst to form a mixture of cis- and trans-1,2-dimethylcyclohexane. Treatment of X with ozone follwed by zinc in aqueous acid gives a ketone plus formaldehyde (CH2=O). What is the structure of X?

Compound X has the formula C8H14.

X reacts with one molar equivalent of hydrogen in the presence of a palladium catalyst to form a mixture of cis- and trans-1,2-dimethyl cyclohexane. Treatment of X with ozone followed by zinc in aqueous acid gives a ketone plus formaldehyde (CH2=O). What is the structure of X?

Explanation:

The degree of unsaturation in the given molecule C8H14 is:

DU=(Cn+1)-Hn/2-Xn/2+Nn/2

where,

Cn=number of carbon atoms

Hn=number of hydrogen atoms

Xn=number of halogen atoms

Nn=number of nitrogen atoms

C8H14:

DU=(8+1)-14/2

=>DU=9-7 =2

Hence, the given molecule will have either two double bonds or one double bond and one ring or two rings.

X reacts with one molar equivalent of hydrogen in the presence of a palladium catalyst to form a mixture of cis- and trans-1,2-dimethylcyclohexane.

This indicates that the molecule X has one double bond and one ring that is cyclohexane ring.

Treatment of X with ozone follwed by zinc in aqueous acid gives a ketone plus formaldehyde (CH2=O).

So, the molecule has a ring and double bond CH2.

Based on the given data the structure of compound X is shown below:

The reaction sequence is shown below: