[dornishthunder]

Butane is the only carbon source allowed.

My attempt thus far: I noticed that there are 12 carbons, with butane being my starting material I decided to break it up into three butane groups. One butane group I chlorinated and then used H20 to make butanol, I figured I could later turn it into the ketone with something like Na2Cr2O7. I'm unsure how to proceed now. I can't seem to get the corey-house to work and this is the only method I know to connect smaller alkanes.

Synthesizing 5-propyl-4-nonanone from butane.

[dornishthunder]

Even if no one can find out the answer, some suggestion of what to look at to help me would be great. I went over every chapter carefully and all the homework problems, and googled for a good hour and still have no idea how to proceed.

[discodermolide]

looks like it may be making butyraldehyde and butyl bromide and see where you can go from there?

[curiouscat]

If you tried going via Octane:

What major products do I expect on free radical halogenation of n-octane? C2, C3 and C4 are all 2° Carbons; I'm trying to think which is most reactive.

If you could get 4-halo-octane that might give you some way forward?

[discodermolide]

looks like it may be making butyraldehyde and butyl bromide and see where you can go from there?

I have a scheme for you but you must show me some of your ideas.

[orgopete]

This does not look like a Corey-House product. I'm guessing you have just gone over Grignard reactions. If you succeeded in making butanol, you are one the right track. How might you make the intermediate 4-octanol from butane?