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10. Protonation of carboxylic acid may occur either on the hydroxyl group or on the carbonyl oxygen to give structures 1 and 2. (5

 

10. Protonation of carboxylic acid may occur either on the hydroxyl group or on the carbonyl oxygen to give structures 1 and 2. (5 pts) Substituent H 2 The equilibrium constants for protonation of a number of substituted benzoic acids have been determined. CO,H pk Drom OH 7.26 COH + H+ m-Me p-Me 7.19 6.92 K m-MeO 7.45 OH* OH p-MeO 6.68 m-Cl p-CI 7.73 7.48 m-NO 7.97 Convert this to Hammet plots using and + and by correlation of the above results with one of these graphs determine the protonation (1 or 2). Explain your answer by showing some illustrations.

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