8.3 Acid Catalyzed Hydration, Oxymercuration Demercuration, and Hydroboration Oxidation | OChemistry

Chad breaks down the three different was of hydrating an alkene: acid-catalyzed hydration, oxymercuration-demercuration, and hydroboration-reduction.
He starts with acid-catalyzed hydration of alkenes showing the reaction mechanism and explaining why it results in Markovnikov addition of H and OH, has no stereoselectivity, and is subject to carbocation rearrangements.

Chad then covers oxymercuration-demercuration of alkenes (aka oxymercuration-reduction) showing the reaction mechanism and explaining why it results in Markovnikov addition of H and OH, and how the halonium ion intermediate results in Anti addition for stereoselectivity and makes carbocation rearrangements not possible.

Third, Chad covers hydroboration-oxidation of alkenes showing the reaction mechanism and explaining why it results in anti-Markovnikov addition of H and OH and results in Syn addition for stereoselectivity.

Finally, Chad shows the product of each reaction on an alkene specially chosen as the difference between each of the three reactions is clear.

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00:00 Lesson Introduction
01:09 Acid-Catalyzed Hydration of Alkenes
03:07 Acid-Catalyzed Hydration Mechanism
06:06 Oxymercuration-Demercuration of Alkenes
07:21 Oxymercuration-Demercuration Mechanism
13:53 Hydroboration-Oxidation of Alkenes
15:35 Hydroboration-Oxidation Mechanism
20:57 Hydration of Alkenes Sample Problem

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