S'21 - Magic 2 - Borane Oxidation - Turning B into O
Автор: Chem240_DJS
Загружено: 2021-04-17
Просмотров: 12
The second "magical"... let's just illustrate some principles... as opposed to believing that the mechanism goes like this:
Principle #1 - Boron both WANTS more electrons, and as soon as it gets them... wants to GET RID OF THEM.
Principle #2 - Electronegative atoms do NOT like to be bound to each other. O-O bonds are QUITE weak. So are Cl-Cl, so are Br-Br, F-F, I-I you get the idea.
These two thoughts combine in the work-up step after a hydroboration. The boron has an empty orbital, and the peroxide we add desperately wants to break that O-O bond.
Timestamps:
0:00 - Why "magic"?
0:24 - Borane is electron deficient... until it's not.
0:58 - X-X bonds are exceptionally weak.
1:36 - what you ACTUALLY need to know.
2:46 - borane gets attacked by peroxide.
3:56 - the peroxide gets broken by a bond migration.
4:45 - what happens next - repeat 2x.
6:10 - Hydroxide swaps out the alcohols.
7:25 - acidic workup.
7:45 - Take-homes.
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