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Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: g_orbital on April 06, 2006, 03:57:47 PM

Title: Tautomerism in 1,3-dicarbonyls
Post by: g_orbital on April 06, 2006, 03:57:47 PM

In 1,3-dicarbonyls there could be theoretically TWO  possible equilibrating enols (beside the keto form), e.g. in acetoacetic ester. My question is: What are the criteria that favor specific enol upon the other one? and how kinetic/thermodynamic conditions control this equilibrium?

Thanks!

Title: Re: Tautomerism in 1,3-dicarbonyls
Post by: movies on April 12, 2006, 02:27:50 PM

Think about which carbonyl group will be a stronger electron withdrawing group in your acetoacetic ester example.