Which of the following acids has the smallest | vedclass

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(C) The dissociation constant $(K_a)$ of a carboxylic acid is directly proportional to its acidity. The acidity is increased by the electron-withdrawi

Vedclass · Accepted Answer

$BrCH_2CH_2COOH$

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(C) The dissociation constant $(K_a)$ of a carboxylic acid is directly proportional to its acidity. The acidity is increased by the electron-withdrawing inductive effect ($-I$ effect) of substituents.$1$. Comparing the substituents: $F$ has a stronger $-I$ effect than $Br$.$2$. Comparing the position: The closer the substituent is to the $-COOH$ group,the stronger the $-I$ effect.$3$. In $CH_3CHFCOOH$ and $CH_3CHBrCOOH$,the halogen is on the $\alpha$-carbon,exerting a strong $-I$ effect.$4$. In $FCH_2CH_2COOH$ and $BrCH_2CH_2COOH$,the halogen is on the $\beta$-carbon,exerting a weaker $-I$ effect.$5$. Between $FCH_2CH_2COOH$ and $BrCH_2CH_2COOH$,$Br$ has a weaker $-I$ effect than $F$.Therefore,$BrCH_2CH_2COOH$ has the weakest $-I$ effect,making it the least acidic and thus having the smallest dissociation constant $(K_a)$.

Which of the following acids has the smallest dissociation constant?

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