1
$\begingroup$

Having learned that aldehydes exist in equilibrium with their hydrate form - Hydrate form of Aldehyde

Do carboxylic acids do the same in a water solvent and form a hydrate with 3 $\ce{OH}$ groups and one alkyl group?

$\endgroup$
4

1 Answer 1

3
$\begingroup$

Let me go against the previous answers, and say that they "do" form hydrates. What you should consider is that the equilibrium towards such hydrates is extremely unfavorable, making them virtually non-existent.

There have been, anyway, clever ways of "blocking" those forms as orthoesters. If I recall correctly, Corey used a protecting group of the OBO family in the synthesis of a natural product.

A more recent paper, which describes a protecting group of that nature, is this: https://pubs.acs.org/doi/abs/10.1021/ol047493n?journalCode=orlef7

Anyway, in normal mechanism-writing, that hydrate is not considered, being highly unfavored and unlikely to form.

$\endgroup$
1
  • 1
    $\begingroup$ Ortho esters are well known (i.e. trimethylorthoformate). Ortho acids are not known $\endgroup$ Commented Aug 25, 2018 at 12:42

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service and acknowledge you have read our privacy policy.

Not the answer you're looking for? Browse other questions tagged or ask your own question.