The hydroboration (of alkenes) reactions I've seen so far, were always followed by oxidation (to yield alcohols).

In those reactions we add $\ce{H2O2}$ & $\ce{NaOH}$ after hydroboration for oxidation.

Today I found a peculiar reaction in which acetic acid was added after hydroboration.

I don't quite understand what exactly happens after the hydroboration part. Can someone enlighten me here?

enter image description here

up vote 9 down vote accepted

Acetic acid effects protonolysis of the borane:

Borane protonolysis

If AcOD is used then RD (instead of RH) is formed.

  • 2
    don't you think the arrows should have been in a reverse manner? – chail10 Dec 15 '17 at 17:23

Your Answer


By clicking "Post Your Answer", you acknowledge that you have read our updated terms of service, privacy policy and cookie policy, and that your continued use of the website is subject to these policies.

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