enolic form of acetoacetic ester is less stable than ketonic form but enolic form of acetyl aceton is more stable than its ketonic form. why?

Dear Nitesh,

In simple aldehydes and ketones ( i.e, acetaldehyde and acetone) the amount of enolic form is negligible. However, if the enolic form is stabilized by intra-molecular hydrogen bonding ( chelation), the amount of enolic form is much greater.

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Aman Bansal

Askiitian Expert

but sir intramolecular hydrogen bonding is present in both the compounds ,i.e enolic form of acetoacetic ester and acetyl acetone..

sir please clear my doubt... i'am very confused..

The enolic form of acetylaceton is more stable because of h-bond and conjugation bw c=o and c=c.In acetoaceticester's inolic form there is a h-bond but because of CROSS CONJUGATION bw (c=o and c=c) and (c=o and oxygen's lp) it is less stable than its ketonic form.Because cross conjugation decrease the stablity of compouds.