Hydration of Alkenes: What You NEED to Know to Ace the Test

In this video I'm going to discuss the ins and outs of the catalytic hydration of alkenes leading to the formation of alcohols.
00:00 What is the hydration of alkenes?
00:56 Which catalyst we should choose for the reaction
01:41 What is the correct first step if this reaction mechanism?
03:14 Why do I need a catalyst to begin with?
04:15 Continue with the mechanism
08:32 Markovnikov's Rule
09:52 Carbocation rearrangements
13:31 Challenge Question
#organicchemistry #organicchemistrytutor #alkenes #markovnikov #hydration
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[@peybak]

That was great. Victor, I remember studying acetal formation with acid catalysts and I remember the book saying it's the alcohol getting protonated first and not the carbonyl. But I guess they meant, that in a separate step alcohol gets protonated, and next carboyl will nab a proton from it and so on. That always bugged me! because they didn't explain why that happens. What you were saying around 2:30 or so, seems to be the same idea, but here it's water getting protonated first. Am I correct?

[@VictortheOrganicChemistryTutor]

Yeah.
When it comes to the mechanisms, we often simplify things and often do so unreasonably. Here, water is the reagent + solvent. What is more statistically likely to happen: direct protonation of an alkene or water? Also, from the equilibrium standpoint, what’s more favorable: formation of oxonium or a carbocation? Same with acetal formation. We often skip the step where we protonate the alcohol which then protonates the carbonyl. But in reality, the most reasonable and thermodynamically favorable step is to get your ROH2+ which *then* serves as your actual acid in the reaction.

[@peybak]

@@VictortheOrganicChemistryTutor Thanks a lot. That makes sense and clears it up. I guess the more I learn, the more I find out I don't knw! It's like the old saying.