JEE MainChemistryGeneral Organic Chemistry
Which of the following compounds has the lowest enol content?
Options
- A3,3-Dimethylpentane-2,4-dione
- B1,3-Diphenylpropane-1,3-dione
- CPentane-2,4-dione
- D3-Oxobutanal
Correct answer
A. 3,3-Dimethylpentane-2,4-dione
Step-by-step solution
The enol content in -dicarbonyl compounds is typically very high due to the formation of a stable, six-membered, intramolecularly hydrogen-bonded ring and extended conjugation. This stabilization requires the presence of at least one -hydrogen atom on the active methylene group situated between the two carbonyl groups. In 3,3-dimethylpentane-2,4-dione, the carbon atom between the two carbonyl groups is bonded to two methyl groups and has no hydrogen atoms. Because the active methylene position is blocked, it cannot