Write the keto-enol tautomerism of ethyl acetoacetate.
Answers
This can be explained with the help of its resonating structures and the +I effect of the groups attached with the carbonyl carbon.
1. When you draw resonating structures of the carbonyl carbon there will be a -ve charge on oxygen. Now this negative charge can be stablised by proton (H+) so the ease with which the attached groups can give the proton will determine the enolic form's stability. Also the no. of acidic H+ available for this is more in acetone than in the aceto ester.
2. This acidity now of the H+ is determined by +I effect of the attached groups on carbonyl carbon. And we know that +I effect of 2 acetic groups is more than +I effect on 1 acetic and one ester group.
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