The two carboxyl groups in 3-chlorohexanedioic acid are not equivalent and thus have different dissociation constants

Chemistry Sep 09, 2020

The two carboxyl groups in 3-chlorohexanedioic acid are not equivalent and thus have different dissociation constants. which carboxylic group is more acidic?

Expert Solution

The structure of 3-chlorohexandioic acid is: HOOC-CH2-CH2-CH-CH2-COOH
|Cl Since, the Cl group causes negative indutive effect to the molecule, but it is not same distance from both the acid groups, it means that the effect due to Chlorine atom is different for both COOH groups, and will make that group more acidic which is close to it, this means the COOH group at 1-C atom will be more acidic

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