Hydroboration oxidation

Lesson 6 of 9 • 4 upvotes • 13:18mins

Dhirpal

This step is a migration of an alkyl group. The pair of electrons in the C–B bond migrates to oxygen, leading to breakage of C–B and formation of C–O. The O-O bond is weak and also breaks down, forming hydroxide. This migration is very similar to 1,2-hydride and alkyl shifts we’ve seen previously, except that instead of migrating to the empty p orbital on a carbocation, the electron pair is essentially performing an attack on the σ* orbital of the O–O bond. The charge on boron goes from negative to neutral.