Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
Which of the following compounds is the strongest carbon acid?
Options
- ACH ₃ COCH ₂ COOEt
- BCH ₂( COOEt )₂
Correct answer
B. CH ₂( COOEt )₂
Step-by-step solution
The acidity of a carbon acid depends on the stability of the carbanion formed after the removal of a proton. The carbanion is stabilized by the delocalization of the negative charge over adjacent electron-withdrawing groups. In the given compounds, the most acidic protons are generally those of the active methylene group located between two carbonyl groups. For compound (1), CH ₃ COCH ₂ COOEt , the conjugate base is resonance stabilized by one ketone group and one ester group. For compound (2), cyclohexane-1,3-dion