NTA Abhyas JEE Main2020ChemistryGeneral Organic ChemistryPractice
The order of stability of the following tautomeric compound is CH 2 = C ( OH ) - CH 2 - CO - CH 3 I → CH 3 - CO - CH 2 - CO - CH 3 II → CH 3 - C ( OH ) = CH - CO - CH 3 III
Options
- AIII > II > I
- BII > I > III
- CII > III > I
- DI > II > II
Correct answer
A. III > II > I
Step-by-step solution
The enol of beta-dicarbonyl compounds are more stable because of conjugation and intramolecular H-bonding. Thus, the order of stability is, CH 3 − C | = OH CH − C | | O − CH 3 III > CH 3 − CO − CH 2 − CO − CH 3 II > CH 2 = C ( OH ) − CH 2 − CO − CH 3 I I is less stable as (=) bond is not in conjugation with carbonly group. III is most stable due to conjugation of (=) bond and intramolecular hydrogen bonding.