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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Chad, you are gifted by God to teach! thank you so much!!
@ChadsPrep
7 ай бұрын
You're welcome and Thank You.
I just found your channel couple weeks ago and honestly your explanations are crystal clear , especially since I am having problems with understanding my organic chem lectures. You are heaven sent and I just want to thank you.
@ChadsPrep
2 жыл бұрын
You're welcome, Kay - glad you found the channel!
There are two really big organic chemistry KZread channels with millions of subscribers. They need to be taking notes because your videos are the clearest by far!
@ChadsPrep
9 ай бұрын
Thank you very much.
@rubyraptor
7 ай бұрын
100% agree. So much clearer than the others (I’ve tried them all!)
@ChadsPrep
7 ай бұрын
@@rubyraptor Glad the channel is helping you.
This was a great video. Everything was so clear. Preciate you sir 🤝🏽
@ChadsPrep
2 ай бұрын
Glad to hear it!
Heaven sent, so helpful. Ochem actually makes sense now. Your lessons have amazing structure and organization that makes the material easy to follow and understand.
@ChadsPrep
Жыл бұрын
That sounds great - Glad you find the channel so useful!
such an awesome channel, I'm always able to count on your stuff to help me when I need it
@ChadsPrep
Жыл бұрын
Excellent, Tyler - glad to hear it!
Im so glad I found you, your explanations are very clear. Thank you
@ChadsPrep
2 жыл бұрын
We are too, c santrich - You're welcome!
literally just right now I was like hmmm i’m having trouble in this chapter, let me see if chads prep has anything on youtube. i then come to see you posted this video 5 minutes ago. it’s as if you read my mind chad. 😭
@ChadsPrep
3 жыл бұрын
Awesome Mohab! It is advantageous to post these right when they are likely to be watched so I'm trying! But obviously there is a little variation in timing from class to class and school to school and I've also heard that a number of colleges are ending the semester early due to the pandemic so my apologies to any for whom this is posted too late to be of help! Happy studying!🙃
i don't know what i would do for ochem without your videos
@ChadsPrep
8 ай бұрын
Glad the videos are helping you!
it's crazy how some professors don't emphasize teaching specific differences. Super helpful thanks!
@ChadsPrep
2 жыл бұрын
You're welcome, Franco!
somehow understood more in a 20 min video than what I did in my entire lecture. tysm 😄😄😄
@ChadsPrep
7 ай бұрын
You're welcome - Glad you found us!
I love u man ... Pls keep going don't stop ❤️❤️❤️❤️❤️☺️
@ChadsPrep
3 жыл бұрын
Thanks for the feedback! Keep up the learning!
Thank you Chad!!!!!
@ChadsPrep
Жыл бұрын
You're welcome.
you're a genius chad
@ChadsPrep
Жыл бұрын
Thank you - Happy Studying!
19:37 "I've seen once in 20 years, students be on the hook for this." I love the fact that I am the lucky student to be on the hook for this
@ChadsPrep
8 ай бұрын
You win!
@maymunamohamed3783
8 ай бұрын
Same.
Thank you
@ChadsPrep
7 ай бұрын
Welcome!
Hi Chad, My orgo professor says that a more substituted alkene would be less reactive towards acid catalyzed hydration than say something like ethene, since ethene is less stable, and thus more reactive. Yet, it forms the least stable carbocation, so wouldn't it be less reactive than something like 1-methylpropene? Thanks.
Hello Chad, does H2SO4 cat. mean the same thing as H2SO4 dilute?
At 4:50, where did the single H at the left side go?
20:43 soooo if you don’t have 3 alkenes the product wont work? Highly unlikely but random question
Hi Chad! I'm doing chem at uni so unfortunate not off the hook for learning the last step involving peroxide and base for the hydroboration mech. You mentioned that that part of the mech is on your website, but I can't seem to find it - is it ok if you could link it to me pls? Thanks!!
@ChadsPrep
5 ай бұрын
Not a problem. You'll find it at the bottom of this page: www.chadsprep.com/chads-organic-chemistry-videos/hydration-of-alkenes/ 😊
@wel_r
5 ай бұрын
@@ChadsPrep chad, you are the holy grail of organic chemistry. You deserve everything on your bucket list !!
@ChadsPrep
5 ай бұрын
😊😊😊
@ChadsPrep
5 ай бұрын
@@wel_r Happy Studying!
23:30 you drew a racemic mixture but it's anti-addition? Shouldn't it just be the left enantiomer?
@ChadsPrep
9 ай бұрын
Hi Austin! Both enantiomers are the result of anti-addition. Keep in mind the anti addition refers to the relationship between the OH added and the H that is added on the terminal carbon. The enantiomer on the left has the OH on a wedged bond so the H would have been added with a dashed bond. The enantiomer on the right has the OH on a dashed bond so the H would have been added with a wedged bond. It is easy to miss on this one because we are not drawing in the H that was added and it is not on a chiral center anyways. But where the OH added is a chiral center in the product. And remember, when you form 1 chiral center in an alkene addition reaction will always form both R and S (and if it is the only chiral center in the entire molecule then it will be a racemic mixture). And it wouldn't matter if it was syn addition, anti addition, or didn't have any stereoselectivity at all. With only 1 chiral center forming, you get both R and S. Hope this helps!
@austin7843
9 ай бұрын
That makes perfect sense. Thank you so much!!!!!!
CPM=0.6172839
:)
@ChadsPrep
4 ай бұрын
Hydroboration is anti markovnikov bc it doesn’t want to be borane 😂 like the other hydration mechanisms. 15:06