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Using the rules that we developed in this chapter (ARIO), we might have expected these two compounds to have the same pKa. Nevertheless, they are different. Salicylic acid is apparently more acidic than its constitutional isomer. Can you offer an explanation for this observation

Sagot :

Histrionicus

Answer:

The correct answer is

- after deprotonation carboxylic acid stabilizes by binding -OH group with hydrogen bonding in salicylic acid and while it's not possible with its constitutional isomer (para-hydroxy benzoic acid).

The more electronegative atoms are replaced by the H atom of the carboxylic group and form more stabilize carboxylic acid which not takes place in para-hydroxy benzoic acid.

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