Orgo II Tutorial: -OH Synthesis Methods from Alkenes
\({\bf{Three~Basic~Mechanisms:}}\) 1. Oxymercuration-Demercuration (see my Oxy-Dem tutorial) 2. Acid-catalyzed hydration > acid HA (often use H2SO4) hydrates one end of the double bond, creating a cation on the other double bond. The cation is then attacked by water, while the conjugate base from the protonation takes one hydrogen off from the water. > Net result: addition of -OH and -H in the Markovnikov positions 3. Hydroboration oxidation > BH3 and THF used in the first step to add H to the more substitued end and BR2 to the less substituted end (anti-M) > Net result: anti-Markovnikov addition of -OH and -H in the syn position
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after that, H2O2 and -OH must be added (must be done in basic conditions) replaces the BH3 with an OH
Anyway, that's the end of my tutorial, I hope it was a helpful resource. Source material is Organic Chemistry 12th edition by Solomons, et. al.
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