# Designing synthetic route to dicarbonyl compound

It's the last one, where 1,4-dimethylcyclohexane breaks apart into... something.

Here's the workup I have. I want to put out there that I'm not concerned about getting the optimal yield yet. Just making the product.

Free radical addition of $\ce{Br}$ to the 2 position.

Removal of that $\ce{Br}$ and the formation of a double bond via E2 using tBuO-

Breaking apart the structure via ozonolysis.

However, no matter where I place the double bond, I can't get the correct configuration of double bonded Oxygens (ketones and aldehydes, right?). So, I must be doing something wrong. Thoughts?