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Topic: Reaction of carbonyls using sodium ethoxide as reagent  (Read 4032 times)

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Offline saint_john

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Reaction of carbonyls using sodium ethoxide as reagent
« on: December 01, 2010, 12:52:50 AM »
I have this reaction below.... can someone please explain the step-wise mechanism that occurs to obtain the product.

Also, how does the epoxide form ??

thanks

Offline Cesium-137

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Re: Reaction of carbonyls using sodium ethoxide as reagent
« Reply #1 on: December 01, 2010, 08:23:55 AM »
I believe the NaOEt deprotonates one of the acidic protons between the Cl and the carbonyl to form an enolate. The enolate then attacks the carbonyl carbon of acetone, pushing electrons up to the oxygen on acetone. The now negatively charged oxygen attacks the chlorinated carbon, kicking off chlorine and forming the epoxide.

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