What is the correct order of acidity of salic | vedclass

Name: Exam Paper Generator | JEE NEET Paper Generator | Vedclass
Brand: Vedclass
Rating: 5 (35 reviews)

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?

Similar Questions

What happens when $LiAlH_4$ is added to an ester?

Which one of the following compounds forms a red coloured solution on treatment with neutral $FeCl_3$ solution?

Which of the following is the strongest acid?

How many organic products will be formed when the following compound undergoes decarboxylation?
(Image: $A$ substituted cyclopentane ring with two $-COOH$ groups at the same carbon atom,and two $-CH_3$ groups at adjacent carbons.)

Vedclass Test Series

Exam Paper Generator

Online Exam Module