[coolguy99]

Little stumped here...


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?


I can't figure this out.. if you have 1,2-dimethylcyclohexene, when you added H2 in excess, you'd get the hexane that I'm looking for... but to get a formaldehyde through ozonalysis.. I'm not getting that. When you split apart the double bond (that I assume must be in a ring due to the previous part of the Q), aren't you always going to get an aldehyde? a C=O with only 1 H because the other bond goes to the continuing carbon chain?..

[KritikalMass]

Maybe you are dealing with a methylene group.