Question #cdcfc
1 Answer
Here's my explanation.
Explanation:
Acetoacetic acid displays keto-enol tautomerism.
However, the position of equilibrium depends strongly on the solvent.
The enol is the major form in nonpolar solvents, but the keto form is favoured in polar protic solvents.
(Adapted from Master Organic Chemistry)
The enol form is stabilized by two factors:
- intramolecular hydrogen bonding
- extended conjugation
In a polar protic solvent like water or ethanol, the ketone
The lone pairs on the
In effect, the solvent is removing the "free" β-ketoacid as a reactant, so the position of equilibrium moves to the left to restore the equilibrium.
Thus, the enol form becomes the minor component in a polar protic solvent.