Oxymercuration Demercuration Reaction Mechanism

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  • Опубліковано 26 лис 2024

КОМЕНТАРІ • 223

  • @TheOrganicChemistryTutor
    @TheOrganicChemistryTutor  2 роки тому

    Organic Chemistry PDF Worksheets: www.video-tutor.net/orgo-chem.html
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    • @JVC-e7p
      @JVC-e7p Місяць тому +1

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

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    @redwillowofdreams8931 2 роки тому +30

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    @ScottNguyenRCAC 5 років тому +36

    Prof lecture + this vid = perfection

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    @matthewmedina. Рік тому +1

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

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    @shreyaskarsaha9967 2 роки тому +2

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    @valerierachaelwinter4701 3 роки тому +3

    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

  • @adrijeetnanda8134
    @adrijeetnanda8134 4 місяці тому +1

    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

  • @christophemakilanko4704
    @christophemakilanko4704 5 років тому +4

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

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    @Sai1ence 4 роки тому +4

    Things starting to get interesting!

  • @lectures7852
    @lectures7852 3 роки тому +2

    by May 2021 you will be at 3M subs

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      @brax300 5 місяців тому

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  • @abohamzamohamed8288
    @abohamzamohamed8288 2 роки тому +2

    sir
    you must add THF to H2o
    to make a reaction

  • @TheToxicMegacolon
    @TheToxicMegacolon 6 років тому +6

    Thank you, the problems helped a lot!

    • @darshmenon5538
      @darshmenon5538 5 років тому

      welcome

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      @dQ__dU_dW 8 місяців тому +1

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  • @aiyshasulaiman5755
    @aiyshasulaiman5755 4 роки тому +2

    Super helpful video. Thank you so much!

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    ong this guy deserves more

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    Thank you so much sir

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    @ebysco2360 8 місяців тому

    Thank you so much for making this video

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    @subhadeepacharya6894 6 років тому +1

    I love your teaching

  • @lalusona59
    @lalusona59 3 роки тому +3

    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
      @realbruh850 9 місяців тому

      no space for h2o to attack

  • @maruather8588
    @maruather8588 4 роки тому

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  • @kingsleyobuobi7421
    @kingsleyobuobi7421 3 роки тому

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  • @asquire9955
    @asquire9955 Рік тому +1

    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
      @cddancefilm1752 Рік тому +1

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

  • @fadophreumz5865
    @fadophreumz5865 3 роки тому +1

    Why mercury has more than 2 valence electrons?

  • @aiyshasulaiman5755
    @aiyshasulaiman5755 4 роки тому

    Thank you so much!!

  • @ebennani9936
    @ebennani9936 3 місяці тому

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

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    @JohannaBohler-q6o Місяць тому

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  • @lacbo9501
    @lacbo9501 8 днів тому

    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.

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  • @tinimeshack2242
    @tinimeshack2242 2 роки тому

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

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    @mabe1272 4 роки тому

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  • @gersonmorales1139
    @gersonmorales1139 2 роки тому

    What about the intramolecular capture of mercuronium salt?

  • @МашаМаша-ь9й
    @МашаМаша-ь9й 3 роки тому +1

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

    • @WorldisOne
      @WorldisOne 3 роки тому

      Butan-2-ol acetoxymercury

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  • @saphonymousplayer1235
    @saphonymousplayer1235 5 років тому +3

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

    • @sandeep7973
      @sandeep7973 4 роки тому +1

      There is no carbocation formation

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  • @Ririavery
    @Ririavery 3 місяці тому +1

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

    • @zikraadhyastha5828
      @zikraadhyastha5828 Місяць тому +1

      because we dont do rearrangement on the oxymercuration - demercuration

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  • @abohamzamohamed8288
    @abohamzamohamed8288 2 роки тому

    mercuric acetate with water without THF
    does not make any reaction

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  • @fstudies6913
    @fstudies6913 2 роки тому

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

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