8.4 Addition of an Alcohol | Acid-Catalyzed Addition and Alkoxymercuration-Demercuration | OChem
Chad covers two reactions that involve the addition of an alcohol to an alkene resulting in an ether.
Chad first covers acid-catalyzed addition of an alcohol showing how the mechanism is analogous to that of acid-catalyzed hydration explaining why it results in Markovnikov addition of H and OR, has no stereoselectivity, and is subject to carbocation rearrangements.
Chad then covers alkoxymercuration-demercuration showing how the mechanism is analogous to that of oxymercuration-demercuration explaining why it results in Markovnikov addition of H and OR, and anti addition for stereoselectivity, and is NOT subject to carbocation rearrangements.
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00:00 Lesson Introduction
01:09 Acid-Catalyzed Addition of an Alcohol to an Alkene
02:00 Acid-Catalyzed Addition of an Alcohol Mechanism
04:04 Alkoxymercuration-Demercuration of Alkenes
04:40 Alkoxymercuration-Demercuration Mechanism
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At 2:40, when the alkene deprotonates the protonated methanol, is it not more straight forward for the alkene to deprotonate the sulfuric acid, which then creates a carbocation that gets attacked by the alcohol? Or will all the sulfuric acid have already protonated the methanol, so there is no chance for this to happen?
Hey chad a little confused at 2:40. You said when h2SO4 gets in water it turns into H3O+ yet I see a oxygen bonded to two H’s and a CH3. Where did that CH3 come from?
@onespeedbjj3846
Жыл бұрын
The alcohol is the solvent in this reaction not water. So when you put H2SO4 in methanol it will form a protonated methanol and HSO4- as the conjugate base. He was using H3O+ as an example.
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CPM = 0.274599
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