Oxymercuration Demercuration Reaction Mechanism

[@TheOrganicChemistryTutor]

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[@JVC-e7p]

3:32 , The 2nd resonating has 3 membered ring it then how can it be said as more stabl?

[@redwillowofdreams8931]

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

[@ScottNguyenRCAC]

Prof lecture + this vid = perfection

[@albertmanqueros6896]

I am surprised this series has such few views. This guy has helped us all.

[@adrijeetnanda8134]

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

[@brooklynnb7782]

this is where i give up

[@tomatrix7525]

Brooklynn B Don’t give up! I’m finding this hard too, but you will do it? How did you do on your exams? I bet you passed. Do not give up, because that is worst thing you can do. I believe in you

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dont !!!!

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[@matthewmedina.]

After multiple lectures I never understood this but in 90 seconds you made it make sense. God bless you man

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I did poorly on my first exam but your videos are helping me keep up. Thank you for the help boss

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How'd the next one go?

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your teaching is lucid clear

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Things starting to get interesting!

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I love your teaching, you help me for many things.

[@darshmenon5538]

welcome

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Thank you, the problems helped a lot!

[@darshmenon5538]

welcome

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​@@darshmenon5538why the hell are you saying welcome 💀💀

[@lacbo9501]

on 2:23 you talk about the resonance structures of the alkene mercury acetate compound but then u start breaking sigma bonds and the octete rule which wouldn't make what you drew valid resonance structures, I am very confused as to why you did that maybe it was just a mistake or I'm missing something.

[@saphonymousplayer1235]

11:31 is first one major due to inductive effect stabilizing carbocation?

[@sandeep7973]

There is no carbocation formation

[@valerierachaelwinter4701]

The key with OCM watch and practice as much as possible ..expose yourself ..otherwise just watching without doing anything is risking....I watched this video first time it was hardddd ..but the more I practiced the more I got the drift and remembered what The OCM tutor was sayin in this video ..dont be lazy lol ..just practice

[@Ririavery]

Why aren't we doing ring expansion at 8:30?

[@zikraadhyastha5828]

because we dont do rearrangement on the oxymercuration - demercuration

[@aiyshasulaiman5755]

Super helpful video. Thank you so much!

[@abohamzamohamed8288]

sir you must add THF to H2o to make a reaction

[@debashree3012]

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?

[@realbruh850]

no space for h2o to attack

[@ebysco2360]

Thank you so much for making this video

[@subhadeepacharya6894]

I love your teaching

[@darshmenon5538]

thanks

[@lectures7852]

by May 2021 you will be at 3M subs

[@brax300]

3 years later in 2024… almost 8M

[@asquire9955]

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?

[@cddancefilm1752]

My prof said no rearrangement for these reactions. Don’t ask me why … I’ve just accepted it and committed it to memory 😂

[@Kynxs]

ong this guy deserves more

[@ayshaazath4240]

Thank you so much sir

[@fadophreumz5865]

Why mercury has more than 2 valence electrons?

[@ebennani9936]

Why didn't you do a ring expansion for the vinyl pentene and mercury acetate with sodium borohydride reaction

[@gersonmorales1139]

What about the intramolecular capture of mercuronium salt?

[@Anaschro]

On the problem of 7:33, why can't you do a methyl shift?

[@Anaschro]

I assume that hydride/ methyl shifts just aren't a thing for this type of reaction

[@sandeep7973]

No rearranging due to non formation of carbocation

[@tinimeshack2242]

What is the product formed when i carry out oxymercuration-demercuration hydration of a benzyl methyl ketone like 1-phenyl-3-butanone?

[@fstudies6913]

sir pls my question is, are the acetate and the mecury gonna form part of the products for the anti addition?

[@N1tTROxUMP45]

Can someone explain to me why there is no ring expansion at 8:45 ?

[@darshmenon5538]

no time

[@chrisattya5278]

I believe it is because there are no rearrangements with oxymercuration reactions

[@barkhagangwani4066]

no carbocation forms so there is no substitution or expansion

[@NavinKumar-im2gq]

Was the reaction at 11:28 correct?

[@NavinKumar-im2gq]

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

[@darshmenon5538]

it is correct u stupid boy

[@saramatraku6317]

methyl shift?? 8:20

[@p.vamshi5084]

Just OH according to markonvis rule (Oh adds on thw carbon of alkene which has less number of H)

[@МашаМаша-ь9й]

CH3-CH2-CH(OH)-CH2(HgOAc) Как называется это вещество?

[@WorldisOne]

Butan-2-ol acetoxymercury

[@ryanromola6267]

why wouldn't the cyclopentane under go a ring expansion during the time there is a carbocation intermediate?

[@nazehsaad9491]

Rearrangements don't occur in oxymercuration reactions.

[@aiyshasulaiman5755]

Thank you so much!!

[@maruather8588]

man I love you

[@melanierodriguez4168]

are we always adding OH

[@seny3053]

I love you 😖❤️

[@kingsleyobuobi7421]

Thanks man

[@abohamzamohamed8288]

mercuric acetate with water without THF does not make any reaction

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I love you really ❤️

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How old are you?

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15 years

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