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Aldol condensation - enone/enal
ChuC
#1 Posted : Monday, July 19, 2010 1:57:58 AM
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Hi just a quick question regarding the enal

Would it be true that if a ketone were to be deprotonated in the first step (and would therefore be the source of the carbonyl group in the product) an ENONE would be formed instead? (since it'd be an alkene conjugated with a ketone)

Is the deprotonation in the first step unselective?
So if there were two unequivalent carbonyls in the first step (ie. ketone and aldehyde) both an enal and enone would be formed?

I understand that its a small question so you don't have to go all out! Just wanted a clarification.

Thanks in advance!
coordinator
#2 Posted : Thursday, August 19, 2010 9:37:54 PM
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Hi ChuC - in short, you are correct, deprotonation of the ketone would result in the formation of an enone. A good example of this is in intramolecular aldol rxns, such as 2,5-hexanedione in the presence of NaOH and ethanol. Deprotonation occurs on the tertiary methyl group of the ketone (in answer to your second question) and results in an intramolecular attack to form 3-methyl-2-cyclopentenone. In rare cases, deprotonation could technically occur at either adjacent carbon (to the carbonyl) forming two cyclic products (i.e., 2,6-heptanedione in the presence of NaOH and ethanol could technically form both 3-methyl-2-cyclopentenone or [2-methylcyclopropenyl]-ethanone => VERY MINOR) but this would be quite rare.

Much of this however would be well beyond the scope of the MCAT, but are rather interesting conceptually. Good question....

-Matt
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