Alkyne Oxymercuration Demercuration Reaction and Mechanism

Leah4sci.com/Alkyne presents: Alkyne Oxymercuration Demercuration: Reaction and Step-by-Step Mechanism
📺Watch Next: Chain Elongation - Terminal Alkynes • Chain Elongation via A...
Need help with Orgo? Download my free guide ’10 Secrets to Acing Organic Chemistry’ HERE: leah4sci.com/orgo-ebook/
This video shows you the reaction and mechanism for the oxymercuration of alkynes, in which an alkyne reacts with a mercuric ion catalyst to form a ketone product at the more substituted position, following Markovnikov’s rule.
You’ll learn the step-by-step alkyne oxymercuration mechanism, including Keto Enol Tautomerization to isomerize an unstable enol intermediate.
And finally you’ll learn about the regioselectivity when starting with an asymmetrical alkyne
↪ Links & Resources Mentioned In This Video ↩
▸ Alkyne Reaction Series + Cheat Sheet leah4sci.com/alkyne
▸Keto Enol Tautomerization • Keto Enol Tautomerism ...
▸Markovnikov’s Rule Leah4sci.com/markovnikov
▸Hybridization Leah4sci.com/hybrid
▸Drawing Skeletal Structures Leah4sci.com/skeletal
▸Carbocation Stability Leah4sci.com/carbocation
▸Retrosynthesis leah4sci.com/organic-chemistr...
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⏱ In this video:
[0:14] Oxymercuration of Alkynes Overview
[1:14] Alkene Oxymercuration Review
[2:10] Shortcut for Drawing the Alkyne Oxymercuration Product
[3:02] Forming the Mercurinium Ion Intermediate
[4:53] Hydration of Intermediate at Markovnikov Position
[6:48] Keto Enol Tautomerization to Form Ketone Product
[9:10] Review of Regioselectivity
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Пікірлер: 37

  • @g.davidtenenbaum8563
    @g.davidtenenbaum85632 жыл бұрын

    Leah's course can definitely make the difference between understanding the material which is required to get a really good grade and trying to memorize the new york phone book. I shared some of Leah's videos with chemistry professors and friends of mine steeped in organic chemistry and the consensus is Leah's course is exceptional. As a bar candidate, I sought out the best bar prep course which definitely made taking the bar exam a one time event. I have no doubt that Leah's course will do the same for orgo students.

  • @Leah4sci

    @Leah4sci

    2 жыл бұрын

    oh wow thank you so much!! I really appreciate the kind words :) hahaha please don't memorize the phone book, sounds terrifying!!

  • @watchrocksgrow
    @watchrocksgrow2 жыл бұрын

    Thank you so much for this! Can't wait for your video on hydroboration-oxidation of alkynes!

  • @Leah4sci

    @Leah4sci

    2 жыл бұрын

    This one? leah4sci.com/hydroboration-oxidation-of-alkenes/ Happy to help!

  • @fengalex9961
    @fengalex9961 Жыл бұрын

    Thank you so much Leah!!! I love you!!

  • @Leah4sci

    @Leah4sci

    Жыл бұрын

    you're welcome.

  • @pexaminer
    @pexaminer2 жыл бұрын

    Great video!

  • @Leah4sci

    @Leah4sci

    2 жыл бұрын

    Thanks!

  • @atharva4180
    @atharva41802 жыл бұрын

    This really helps me in my exams, thanks. At least this isn't the most difficult thing in High School :P

  • @Leah4sci

    @Leah4sci

    2 жыл бұрын

    Perfect timing!

  • @spectroxis6418
    @spectroxis64182 жыл бұрын

    Ok she's definetly following a syllabus, my class legit just covered this today kek

  • @Leah4sci

    @Leah4sci

    2 жыл бұрын

    Wow talk about perfect timing! I asked my students what to cover next so I'm guessing quite a few of them are following a similar pace/curriculum as your professor. Glad this came at the right time

  • @BSbscchemistry-wc6kt
    @BSbscchemistry-wc6kt Жыл бұрын

    Thank you Mam .😊

  • @Leah4sci

    @Leah4sci

    11 ай бұрын

    you're so welcome

  • @JohnCena-sc9id
    @JohnCena-sc9id2 жыл бұрын

    Thanks for such wonderful explanation, but can you please explain how Hg+ was removed in the final step

  • @Leah4sci

    @Leah4sci

    2 жыл бұрын

    As you see in the text of the video, that step is typically not taught in the undergraduate Organic Chemistry curriculum. Since I don't offer tutoring over social media, for help with questions like this and more, I recommend joining the organic chemistry study hall. Details: leah4sci.com/join or contact me through my website leah4sci.com/contact/

  • @andreasgriesser3711
    @andreasgriesser3711 Жыл бұрын

    What a video

  • @Leah4sci

    @Leah4sci

    Жыл бұрын

    Thank you! I hope you've liked it.

  • @namanbhardwaj6432
    @namanbhardwaj64322 жыл бұрын

    MAM PLEASE MAKE A VIDEO ON HOW TO MAKE STRUCTURES OF COMPOUNDS, NOT FOLLOWING THE OCTET RULE,...... AND HOW TO IDENTIFY WHEN IN A STRUCTURE WE HAVE TO REPLACE + AND - WITH A COVALENT BOND AND WHEN WITH A COORDINATE....... 🙏🙏🙏

  • @Leah4sci

    @Leah4sci

    2 жыл бұрын

    Thanks for the recommendation. I post free videos as I have time and am always looking for suggestions. For more help with this topic in the meantime, contact me through my website: leah4sci.com/contact

  • @richardkula437
    @richardkula437 Жыл бұрын

    Very helpful tutorial but What happened to the electrons from the Hg+ when broken? You did not show the electrons in the mechanism. I'm bit curious about this.

  • @Leah4sci

    @Leah4sci

    Жыл бұрын

    Thank you! Because this step is quite complicated and not taught in most undergrad classes, I simply provided an overview of what happens here without showing how the specific atoms and electrons make it happen.

  • @pranjalpagaria322
    @pranjalpagaria3222 жыл бұрын

    I studied from u 2 years back in my high school

  • @Leah4sci

    @Leah4sci

    2 жыл бұрын

    Oh wow, you learned all this in high school? that's impressive!

  • @pranjalpagaria322

    @pranjalpagaria322

    2 жыл бұрын

    @@Leah4sci Ya , I am from India

  • @atharva4180
    @atharva41802 жыл бұрын

    Helpful for my High school exams next month thank you

  • @Leah4sci

    @Leah4sci

    2 жыл бұрын

    Wow! Where do you go to school that you're learning this in high school?

  • @atharva4180

    @atharva4180

    2 жыл бұрын

    @@Leah4sci India. Preparing for JEE Advance. Also, what do you mean preparing in high school? When do you learn all this stuff?

  • @Leah4sci

    @Leah4sci

    2 жыл бұрын

    Undergrad. We barely did any chemistry (or difficult science) in high school

  • @atharva4180

    @atharva4180

    2 жыл бұрын

    @@Leah4sci Oh, so I guess it comes under "easy" category in undergrad if it is taught in high schools. Which year undergrad is it taught?

  • @bijayapanda2673
    @bijayapanda26732 жыл бұрын

    HgSO4 is a weak electrolyte, so the concentration of Hg^2+ ion will decrese in presence of H2SO4 due to common ion effect. Why can't we use other acid like H3PO4.

  • @Leah4sci

    @Leah4sci

    2 жыл бұрын

    That's an interesting question. I don't believe HgSO4 is a weak electrolyte. Even so, the presence of the strong acid is not necessary for this reaction to proceed. Any mercuric ion in solution will lead to an oxymercuration reaction with the alkyne.

  • @3nControlLP
    @3nControlLP2 жыл бұрын

    At 6:25 you simply Break the Hg-Bond and you give the lone pair to the carbon. Isnt that wrong? You would have a 5bonded carbon and Just one H at the carbon... I think it would be better to understand of you attack H3O+ with that Lone pair to get to the ch2group.

  • @Leah4sci

    @Leah4sci

    2 жыл бұрын

    That part of the mechanism is more complicated than what I show, that's why I have a note on the screen that it's not required. My students typically don't learn this and are simply told to skip that step. It is awesome though to recognize that it wouldn't happen exactly as shown

  • @pulkitbhardwaj7055
    @pulkitbhardwaj70552 жыл бұрын

    This reaction is catalytic acidic hydration not oxymercuration-demercuration

  • @Leah4sci

    @Leah4sci

    2 жыл бұрын

    I disagree. Though both would produce the same products, the difference is in the reagents used (and the mechanism). Hydration of an alkyne in acid would use only H2SO4 in water, while oxymercuration uses the HgSO4.

  • @pulkitbhardwaj7055

    @pulkitbhardwaj7055

    2 жыл бұрын

    @@Leah4sci if you use only H2SO4 then the reaction will not proceed as H+ is competitively weak nucleophile and not capable to attack on triple bond (Alkyne)

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