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

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

Grade:12

1 Answers

AskiitianExpert Shine
10 Points
12 years ago

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.

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