Question

Why the enol form of ethyl acetoacetate is more stable than enol form of acetone?

Answer 1

Answer:

Ethyl acetoacetate has about 0.5% enol, when dissolved in water. The main reason is that a carbonylbond (C=O) is very stable compared to the corresponding C=C in the enol

Answer 2

I am not an organic chemist, so this is not my area of specialization, but I’d say that is because oxygen is more electronegative than carbon, so it draws the electrons available for double-bonding to it and away from the other carbon (the far one in the ‘ene’ group). I remember learning about ketone-enol (or keto-enol) tautomerism (if I spelled that correctly) in organic chemistry. I bet every organic chemistry text out there will cover this question. Please refer to yours. I no longer have mine. Good Luck