Can carboxyllic acids form hydrates?

[airstrikee]

If we had a carboxyllic acid like benzoic acid that is treated with an acid such as HCl what would be the major product? Would it be a hydrate? I've attached a picture of a mechanism i made

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[amy_k]

Looks feasible but I would call that a triol or an ortho-acid, not a hydrate.

 

[Teleologist]

http://en.wikipedia.org/wiki/Orthoacetic_acid

Steps 1 and 2 in your hypothetical mechanism are uphill journeys, both enthalpically and entropically. I don't see why this would be something that occurs on a large scale unless you had some very, very strong acid. Even then, entropy isn't exactly on your side.

 

[airstrikee]

http://en.wikipedia.org/wiki/Orthoacetic_acid

Steps 1 and 2 in your hypothetical mechanism are uphill journeys, both enthalpically and entropically. I don't see why this would be something that occurs on a large scale unless you had some very, very strong acid. Even then, entropy isn't exactly on your side.

Ah, so what is a possibility for a major product when adding an acid such as HCl to a carboxyllic acid?

 

[Teleologist]

I would think that the carboxylic acid stays mostly intact.