[TheQuestion90]

My study group and I have been stuck on this problem for awhile now, and I don't know what else to try. I can do the wittig reaction but then I don't get how to acid catalyze the wittig Product. Usually with Acid Catalyzed Hydration there is a proton transfer then Nuc Attack but I don't see how that can happen in what I am given. I have attached pictures of the problem and my most recent work to the problem.

Thanks for taking the time to assist

[discodermolide]

please orientate the pictures the correct way up, I get a sore neck looking at them, and increase the contrast so they are legible. Thanks

[TheQuestion90]

Is that better??

[discodermolide]

Yes. The Wittig product is ok.
The hydrolysis mechanism needs a bit of work it is just the hydrolysis of an enol-ether by a dic to regenerate the aldehyde.But you get there in the end.

[AlphaScent]

hydrolyzed by a dic?

[discodermolide]

damm spell checker, don't know how to turn it off.

[AlphaScent]

I figured...I laughed pretty hard