The order of stability of the following tautomeric compounds is [figure]
- II > I > III
- II > III > I
- I > II > III
- III > II > I
Answer
(4) III > II > I
Solution
I and III are enol forms and II is the keto form (pentane-2,4-dione) of the same compound.
∵ In I the C=C bond is isolated; it is not conjugated with C=O and there is no intramolecular H-bond.
⇒ I is the least stable form.
∵ In III the C=C bond is conjugated with C=O, and the enolic –OH forms an intramolecular hydrogen bond with the C=O oxygen (a stable six-membered ring).
⇒ III is more stable than the keto form II (pentane-2,4-dione exists mainly in the enol form).
∴ Order of stability: III > II > I
Answer: (4)