Which of the following will undergo deprotona | vedclass

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(A) The ease of deprotonation depends on the stability of the resulting carbanion. The carbanion is stabilized by the electron-withdrawing effect of t

Vedclass · Accepted Answer

$a$

Vedclass · Answer

(A) The ease of deprotonation depends on the stability of the resulting carbanion. The carbanion is stabilized by the electron-withdrawing effect of the adjacent carbonyl groups. In compound $b$ (dimethyl malonate),the central carbon is flanked by two ester groups $(-COOCH_3)$. The ester group is less electron-withdrawing than a ketone group due to the $+M$ effect of the oxygen atom. In compound $a$ (acetylacetone),the central carbon is flanked by two ketone groups $(-COCH_3)$. Ketones are more electron-withdrawing than esters. In compound $c$ (methyl acetoacetate),the central carbon is flanked by one ketone and one ester group. The acidity of the $\alpha$-hydrogens follows the order: $a > c > b$. Therefore,compound $a$ will undergo deprotonation most readily.

Which of the following will undergo deprotonation most readily in a basic medium?

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