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Grade 12Organic Chemistry

Why does a polar protic solvent tend to stabilize the keto form relative to the enol form?

Profile image of sumit kumar
17 Years agoGrade 12
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1 Answer

Profile image of AskiitianExpert Shine

Hi

The enol form is least polar of the two tautomers , because intramolecular hydrogen bonds help reduce the dipole dipole interaction(repulsion) of the carbonyl groups, this is unreduced in the keto form. furthermore the enol stabilisation due to intramolecular h bonding would be more when intermolecular h bonding does not compete.

Thus a change to more polar solvent increases the tendency of intermolecular h bonding, and thus enol conc decreases.