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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: g-bones on August 28, 2009, 04:38:22 PM

Title: protection of the carbonyl of an enone
Post by: g-bones on August 28, 2009, 04:38:22 PM

I am reviewing some problems and I have the attached problem in which i am given the starting material and the reagents and must predict the product.  when I first looked at it I didn't think much and came up with the reaction path and the product shown.  the only thing I am worried about is whether the formation of the acetal will be productive or whether a michael addition would occur instead thus destroying the double bond and not giving the ozone anything to react with.  anybody have any thoughts.

Title: Re: protection of the carbonyl of an enone
Post by: Arctic-Nation on August 30, 2009, 04:45:18 PM

I don't really expect any problems. Some side reactions might occur, but oxygen loves hard-hard interactions, so glycol addition should only happen at the carbonyl-carbon, not at the beta-position.