Which of the following compounds would you ex | vedclass

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(B) The acidity of a carbon acid depends on the stability of the conjugate base formed after the removal of a proton. In $CH_2(CO_2Et)_2$ and $CH_3COC

Vedclass · Accepted Answer

Bicyclo[$2.2$.$1$]heptane$-2,3-$dione

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(B) The acidity of a carbon acid depends on the stability of the conjugate base formed after the removal of a proton. In $CH_2(CO_2Et)_2$ and $CH_3COCH_2COOC_2H_5$,the conjugate base is stabilized by resonance with two carbonyl groups. However,in bicyclic systems,the acidity is significantly influenced by the geometry. In bicyclo[$2.2$.$1$]heptane$-2,3-$dione,the two carbonyl groups are adjacent to each other. The removal of a proton from the bridgehead or adjacent carbon creates a carbanion that is stabilized by the inductive and resonance effects of the two adjacent carbonyl groups. Specifically,the enolate formed from bicyclo[$2.2$.$1$]heptane$-2,3-$dione is highly stabilized due to the proximity of the two carbonyl groups,making it a stronger carbon acid compared to the others listed.

Which of the following compounds would you expect to be the strongest carbon acid?

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