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?

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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

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