Apparently, for keto-enol tautomerism, the enol content of a given carbonyl compound increases when in a non-polar solvent.
What is the reason for this?
Chemistry Stack Exchange is a question and answer site for scientists, academics, teachers, and students in the field of chemistry. It only takes a minute to sign up.Sign up to join this community
In diketone example acetyl acetone ........... Enol content in water is 15% but enol content in hexane is 92% . Reason... Water form hydrogen bond with Co group of keto form which reduce the intramolecular hydrogen bonding of enol form. Hence enol content increase in non polar aprotic solvent example hexane but increase in polar protic or polar aprotic solvent example water acetone. Enol content order in different solvent Hexane >benzene >acetone >methanol >water