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Can carboxyllic acids form hydrates?

Discussion in 'MCAT Study Question Q&A' started by airstrikee, 10.29.14.

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  1. airstrikee

    airstrikee 2+ Year Member

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    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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  3. amy_k

    amy_k

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

    Teleologist 2+ Year Member

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    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.
     
    Last edited: 10.30.14
  5. airstrikee

    airstrikee 2+ Year Member

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

    Teleologist 2+ Year Member

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    I would think that the carboxylic acid stays mostly intact.
     

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