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Give two evidences in support of enolic or ketonic form of acetoacetic ester.

Give two evidences in support of enolic or ketonic form of acetoacetic ester.

Grade:12th pass

2 Answers

Arun
25750 Points
4 years ago
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. 
Hence the reasoning.
 
Vikas TU
14149 Points
4 years ago
Enolic form of acetoacetic ester is less stable than ketonic form but enolic form of acetyl acetone is more stable than its ketonic form. ... Here, in case of acetyl acetone if we draw the structure there are two methyl groups which gives -OH bonding correspondingly two times each from two sides so there are two H-bonding.

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