Grignard Attacks Nitrile to Form Ketone - Reaction and Mechanism
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- Опубліковано 21 лют 2022
- Leah4sci.com/Grignard presents: Grignard reacting with a nitrile to form a ketone, complete reaction and step by step mechanism
📺Watch Next: Organometallic Reagents and Reactions • Organometallic Reagent...
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Grignard reagents are my go-to for chain elongation reactions in orgo 2. This video takes you through the reaction and mechanism of a grignard attacking a nitrile to form a ketone as well as showing you the steps for hydrolysis of the imine intermediate.
You’ll learn the step-by-step mechanism for breaking each of the bonds between the carbon and nitrogen through a sequence of proton transfers and see how a water molecule attacks the iminium ion intermediate to form a new bond to oxygen.
You’ll also learn a shortcut for predicting the structure of the final product.
↪ Links & Resources Mentioned In This Video ↩
▸Grignard Series + Cheat Sheet Leah4sci.com/Grignard
▸Polar and Nonpolar Covalent Bonding • Ionic, Polar Covalent ...
▸Functional Groups Guide Leah4sci.com/functional-group...
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⏱ In this video:
[0:15] Overview of Reaction
[0:33] Why a Grignard Attacks a Nitrile
[0:50] Mechanism for the Grignard and Nitrile Reaction
[1:47] Formation of Imine Intermediate
[4:08] Ammonia Leaving Group
[5:10] Final Ketone Product
[5:53] Shortcut for Predicting Final Product
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perfect timing, this is exactly what we’re learning in ochem2
Glad this came at the right time! Hope the trick helps you save time
Hats off to your contribution in the field of organic reaction mechanisms and product guessing. Great 👌 job , nice fundamental explanation of how the things go on during a reaction. Full credit to you for creating the channel and providing best quality education in the world about organic reactions.
You're so very welcome, and thanks so much for your kind words!
@@Leah4sci go ahead
The way you have explained is such what the actual quality of teaching is required from the professors to the students for better understanding of concepts in organic reactions
I appreciate your kind words, and I'm so happy to help you and others better understand.
@@Leah4sci waiting for many more concepts of mechanisms explanation in organic reactions
oh! what a teaching way absolutely delightful
Glad you found this helpful
Thankyou so much 🫂💗
you're very welcome
wow did not now grignard was THAT important in organic chemistry, thanks for the hint with the cheat sheet, nice and quick video and well thought out didactics
You're very welcome! I love using grignards for synthesis at the orgo 2 level
Too good ma'am 👍...Subscribed
Thanks so much! 😊
Excellent lecture and full of information.. Nice mam
Thank you
You really helped me in my reaction mechanism concept of jee
Happy to help!
Hi, from Turkey your videos really benefical thanks😊 I will be chemist soon
You're so welcome!
THANK YOU 😀
You're welcome!
I remember where they told me that grignard’s reagents are too active and when we reduce a compound to ketone, it doesn’t stop there and the remaining Grignard reagent reacts with the formed ketone to make it an alcohol!
That’s why ig we use nitriles so that it can stop at the ketone step.
Btw can we also use Corey house reagent I guess it was gilman’s reagent to stop at ketone because it’s also not much active as compared to grignards reagent??
When I think of grignards not stopping at ketone I think of something like an ester getting attacked. This reaction destroys the grignard and has no way to continue past the ketone since we lose the grignard way before. As for C-H not sure how that ties in here
@@Leah4sci yes ma’am actually now I remember that ketones from nitriles by RMgX doesn’t convert to alcohol because the H+ ions is consumed during hydrolysis of RCN group. Anyways thank you ma’am for replying with the answer. Absolutely appreciate it
Plz make video on Olympiad lvl problem
Sorry, I don't teach for that
is this a substitution or addition reaction?
A Grignard reaction is in its own category of organometallic reactions. It is the addition of an organomagnesium halide to a ketone, aldehyde, nitrile or similar to form an alcohol. For a full review, make sure to see my tutorial at Leah4sci.com/Grignard
@@Leah4sci Thank you very much
M.Sc. of chemistry here: An interesting issue that people need to realize is that a nitrile is a hidden/protected carboxy-group. And then you actually realize it's a redox-reaction. 😉
Yes, thanks for watching! :)