[AhBeng]

Hi,

Assuming there is no error in the question, can an alkene C6H12 (structure is not given; elucidation of structure is the whole point of the question)  be oxidized to give 2 isomeric products of C3H6O?

The question gives no additional information regarding the mechanism/reagents of the oxidation.

The obvious compound with formula C3H6O is propanone, H3C(C=O)CH3. But it is non-isomeric. There is no chiral carbon, no cis-trans isomerism, etc.

There are two (possibly more) other compounds with formula C3H6O, an enol (cis-trans) and an epoxide (chiral C), but neither appears to be obtainable by oxidizing an alkene C6H12.

Thanks in advance for any suggestions!

[azmanam]

you're missing one other compound class with formula C₃H₆O.  Figure it out, and the problem should become clearer.

[AhBeng]

you're missing one other compound class with formula C₃H₆O.  Figure it out, and the problem should become clearer.

Ahh ok, I've solved it. It's an aldehyde. And the oxidation mechanism is oxidative cleavage of the double bond, which produces the ketone and aldehyde.

Thanks (snacks), Azmanam!