Oxymercuration Demercuration Reaction Mechanism
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- Опубліковано 15 вер 2024
- This organic chemistry video tutorial provides a basic introduction into the oxymercuration demercuration reaction mechanism of alkenes into alcohols using Hg(OAC)2 with H2O and NaBH4.
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Syn Vs Anti Addition Test Question:
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Alkene Epoxidation Test Question:
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Alkoxymercuration Demercuration Test Question:
• Alkene + Hg(OAc)2 - Al...
Ozonolysis Test Question:
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Holy crud I might cry, it's near the end of the semester and I've discovered this guy's Ochem full playlist. I will watch these and study them for my primary ochem knowledge through the end of ochem 1 and all of ochem 2. He even made final exam reviews for both...OChem tutor, you are my hero now, I'm not even kidding, I am on the verge of tears of relief
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Things starting to get interesting!
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The video explains the oxymercuration-demercuration reaction of alkenes, its regioselectivity, and mechanism. It also provides a practice problem and offers100 multiple choice problems for a chemistry final exam.
[00:00] The video explains the oxymercuration demercuration reaction of alkanes
- The reaction involves reacting an alkene with mercury two acetate and water
- The oxymercuration step adds an OH group to the more substituted carbon and mercury to the less substituted carbon
- The demercuration step removes the mercury and replaces it with a hydrogen atom using sodium borohydride
- The mechanism involves the ionization of mercury acetate, attack of the alkene on the mercury atom, and stabilization of the intermediate by resonance
[03:00] Oxymercuration reaction produces a racemic mixture of both R and S two-butanol.
- Secondary carbons with a positive charge are more stable than primary carbons
- The major resonance contributor is the most stable resonance structure
- Water attacks the secondary carbon atom due to its higher partial positive charge
- The oxymercuration step involves using a base to remove a hydrogen atom
- Sodium borohydride is added in the final step to get the alcohol product
[06:05] Oxymercuration reaction does not undergo rearrangement and results in OH group on more substituted carbon atom of double bond
- No rearrangement occurs in oxymercuration reaction
- OH group is added to the more substituted carbon atom of the double bond
- Results in a racemic mixture of products
[09:05] The oxymercuration reaction results in anti-addition and can produce enantiomers
- The O-H group and mercury acetate group must be on opposite sides
- The alcohol group can be placed on either carbon atom of the double bond
- For a non-chiral carbon, only one stereoisomer is produced
- For a chiral carbon, two stereoisomers can be produced with the O-H group on the wedge or dash
Thank you, the problems helped a lot!
welcome
@@darshmenon5538why the hell are you saying welcome 💀💀
Super helpful video. Thank you so much!
sir
you must add THF to H2o
to make a reaction
Thank you so much sir
Thank you so much for making this video
Sir, in the hybrid structure, the +ve charge on Hg>+ve charge on 2°C atom>+ve charge on 1°C atom.Now,H2O is a nucleophile.Then it should attack the most electron deficient region of the hybrid that is, the Hg atom.But instead of that it attacks the 2°C atom.Why is this so?Could you explain?
no space for h2o to attack
ong this guy deserves more
I love your teaching
thanks
Why aren't we doing ring expansion at 8:30?
by May 2021 you will be at 3M subs
3 years later in 2024… almost 8M
Why didn't you do a ring expansion for the vinyl pentene and mercury acetate with sodium borohydride reaction
In the first example, why did the carbocation not shift to the left since it has more alpha-H and will be stabilized by hyper-conjugation?
My prof said no rearrangement for these reactions. Don’t ask me why … I’ve just accepted it and committed it to memory 😂
Why mercury has more than 2 valence electrons?
11:31 is first one major due to inductive effect stabilizing carbocation?
There is no carbocation formation
Thank you so much!!
What is the product formed when i carry out oxymercuration-demercuration hydration of a benzyl methyl ketone like 1-phenyl-3-butanone?
sir pls my question is, are the acetate and the mecury gonna form part of the products for the anti addition?
Thanks man
man I love you
What about the intramolecular capture of mercuronium salt?
CH3-CH2-CH(OH)-CH2(HgOAc)
Как называется это вещество?
Butan-2-ol acetoxymercury
Ullrich Extension
Ariel Walks
Oberbrunner Ferry
Cara Street
are we always adding OH
Theodora Manors
mercuric acetate with water without THF
does not make any reaction
I love you really ❤️
Claudia Villages
Elinor Forges
Emma Key
Freddie Courts
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How much did you get
Ebert Groves
methyl shift?? 8:20
why wouldn't the cyclopentane under go a ring expansion during the time there is a carbocation intermediate?
Rearrangements don't occur in oxymercuration reactions.
Spencer Vista
Great
welcome
Beahan Extension
On the problem of 7:33, why can't you do a methyl shift?
I assume that hydride/ methyl shifts just aren't a thing for this type of reaction
No rearranging due to non formation of carbocation
How old are you?
15 years
Quigley Run
Alayna Trace
Damon Ramp
Was the reaction at 11:28 correct?
I thought the one at the right was primary so you'd only have one place for the nucleophile to attack but then again I am not the best o chem student around so idk
it is correct
u stupid boy
Can somebody help Me? !!
My exam is tomorrow 😭
Can someone explain to me why there is no ring expansion at 8:45 ?
no time
I believe it is because there are no rearrangements with oxymercuration reactions
no carbocation forms so there is no substitution or expansion
Nyc
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Senger Run
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Romaguera Dale
Damn
Mayra Shore
Thumbnail inaccurate, terrible job