Consider the pKa values of the following constitutional isomers: OH O OH pKa = 3.0

Chapter 3, Problem 3.57

(choose chapter or problem)

Consider the pKa values of the following constitutional isomers: OH O OH pKa = 3.0 Salicylic acid O OH HO pKa = 4.6 para-Hydroxybenzoic acid 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?

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