[mugsy777]

Hello all!

Can anyone help me rationally explain why ethyl acetoacetate exists (in a non-polar solvent) mainly in it's keto form? Obviously the keto form is more stable, but I'm looking for a more technical explanation. I am contrasting the keto-enol equilibium of ethyl acetoacetate with that of acetyl acetone.

I am aware the presence of the ethoxy group is the main justification- however, how does it contribute to instability, besides the fact that it's bulkier? Electronically?