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Topic: MVK addition product?  (Read 4372 times)

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Offline mir

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MVK addition product?
« on: April 03, 2006, 11:45:00 AM »
Hi everyone!

I have a problem with an exercise. Im going to figure out a mechanism, as shown in the image, with my suggestion of a pathway.

But I dont like that substitution step. I find it very hard to imagine a water molecule add nucleophilic to an sp2-hybridized carbon.

Plz give a hint, what is wrong here.
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Offline Albert

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Re:MVK addition product?
« Reply #1 on: April 03, 2006, 12:58:57 PM »
To be honest, I still prefer yours...
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Offline mir

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Re:MVK addition product?
« Reply #2 on: April 03, 2006, 01:15:18 PM »
Well. This exercise was written in a chapter about addition-reactions :-)

So, your suggestion is probably more correct...
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Offline movies

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Re: MVK addition product?
« Reply #3 on: April 12, 2006, 02:13:16 PM »
You guys are close, but a little bit off.  You first protonate the enol on carbon and form an oxocarbenium ion, which is subsequently attacked by water.  Here is the correct mechanism:

« Last Edit: April 12, 2006, 02:15:10 PM by movies »
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