Why is 2,4 pentanedione more highly enolized than 1,3 cyclohexanedione?

1 Answer
anor277
Jun 19, 2016

Enolization of acetylacetone allows a 6-membered ring, stabilized by hydrogen bonding.

Explanation:

On the other hand, when the cyclic dione enolizes, because the oxygen centres are constrained by the ring, and hydrogen bonding would occur intermolecularly, rather than intramolecularly.

I am trying to think how you would be able to test this hypothesis. Maybe the #pK_a# of each dione would be revealing.

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