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Topic: acid-base  (Read 2602 times)

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Offline Imo

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acid-base
« on: April 28, 2012, 09:35:20 PM »
Why salicylic acid is not amphoteric ? The group OH could react with H+ , not?
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Offline Dan

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Re: acid-base
« Reply #1 on: April 29, 2012, 06:53:11 AM »
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Offline orgopete

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Re: acid-base
« Reply #2 on: April 29, 2012, 08:23:40 PM »
Given that phenol is more acidic than water, this means its electrons are less available for protonation than water. The pKa of hydronium ion is circa -1.7. The pKa of the conjugate acid of the protonated species would have to be more than the pKa of the carboxylic acid, ca. 4. Oxygen just isn't basic enough.
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