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Topic: Wittig Reaction problem.  (Read 3158 times)

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Offline TheQuestion90

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Wittig Reaction problem.
« on: March 10, 2014, 09:45:11 PM »
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
« Last Edit: March 10, 2014, 10:07:32 PM by TheQuestion90 »

Offline discodermolide

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Re: Wittig Reaction problem.
« Reply #1 on: March 10, 2014, 10:00:49 PM »
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
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Offline TheQuestion90

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Re: Wittig Reaction problem.
« Reply #2 on: March 10, 2014, 10:07:53 PM »
Is that better??

Offline discodermolide

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Re: Wittig Reaction problem.
« Reply #3 on: March 11, 2014, 02:54:45 AM »
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.
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Offline AlphaScent

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Re: Wittig Reaction problem.
« Reply #4 on: March 11, 2014, 12:08:36 PM »
hydrolyzed by a dic?
If you're not part of the solution, then you're part of the precipitate

Offline discodermolide

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Re: Wittig Reaction problem.
« Reply #5 on: March 11, 2014, 12:18:08 PM »
damm spell checker, don't know how to turn it off.
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Offline AlphaScent

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Re: Wittig Reaction problem.
« Reply #6 on: March 11, 2014, 01:01:05 PM »
I figured...I laughed pretty hard
If you're not part of the solution, then you're part of the precipitate

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