Among the following,the marked proton of whic | vedclass

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(C) The $pK_{a}$ value is inversely proportional to the acidity of the compound. The acidity depends on the stability of the conjugate base formed aft

Vedclass · Accepted Answer

$C_6H_5-CH_2-CO-CH_3$ (marked $H$ on benzylic carbon)

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(C) The $pK_{a}$ value is inversely proportional to the acidity of the compound. The acidity depends on the stability of the conjugate base formed after the removal of the proton.$1$. In $A$,the conjugate base is stabilized by resonance with the carbonyl group,but it also experiences cross-conjugation with the $-OH$ group.$2$. In $B$,the conjugate base is stabilized by resonance with the carbonyl group.$3$. In $C$,the conjugate base is stabilized by resonance with the carbonyl group $AND$ the phenyl ring,making it highly stable.$4$. In $D$,the conjugate base is stabilized by resonance with the carboxylate group,but it is less stable than $C$ due to the nature of the resonance.Comparing the stability of the conjugate bases,the benzylic proton in $C$ $(C_6H_5-CH_2-CO-CH_3)$ forms the most stable conjugate base due to extended conjugation with both the phenyl ring and the carbonyl group. Therefore,it is the most acidic and has the lowest $pK_{a}$ value.

Among the following,the marked proton of which compound shows the lowest $pK_{a}$ value?

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