What is the correct order of acidity of salic | vedclass

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Question

(A) The acidity of these compounds depends on the stability of their conjugate bases. $2,6-$dihydroxybenzoic acid has two $-OH$ groups at ortho positi

Vedclass · Accepted Answer

$2,6-$dihydroxybenzoic acid > salicylic acid > $4-$hydroxybenzoic acid

Vedclass · Answer

(A) The acidity of these compounds depends on the stability of their conjugate bases. $2,6-$dihydroxybenzoic acid has two $-OH$ groups at ortho positions relative to the $-COOH$ group. The conjugate base is highly stabilized by strong intramolecular hydrogen bonding between the carboxylate oxygen and both ortho-hydroxyl groups. Salicylic acid ($2-$hydroxybenzoic acid) has only one ortho $-OH$ group, providing less stabilization than $2,6-$dihydroxybenzoic acid. $4-$hydroxybenzoic acid lacks ortho-stabilization and the $-OH$ group at the para position exerts an electron-donating effect ($+M$ effect), which destabilizes the carboxylate anion, making it the least acidic. Therefore, the correct order is: $2,6-$dihydroxybenzoic acid > salicylic acid > $4-$hydroxybenzoic acid.

What is the correct order of acidity of salicylic acid, $4-$hydroxybenzoic acid, and $2,6-$dihydroxybenzoic acid?

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