Chad orgo question...oops??? (Pic inside)

[Cofo]

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i'm confused...why would one of the alpha carbons get deprotonated....since Chad's nucleophile DOES have a hydrogen directly bonded to it?

 

[yappy]

edit: http://www.chemtube3d.com/Nucleophilic%20substitution%20at%20the%20carbonyl%20group%20-%20Enamine%20formation.html

Check out where the hydrogen goes in this example. I think it suggests that it leaves as water then a lp has is pulled in to the N.

 

[AllahIsGreater]

secondary amine with a keytone yields an enamine. just remember that forever. in primary we just remove an H2O. this is all you will ever need. i never do mechanisms, to me those are a joke/huge waste of time. orgo is just tricks. if you have any other questions on rxns feel free to pm me, ill help you to the best of my ability.

 

[yappy]

I agree that you dont need to know every mech for the DAT - but it's foolish to call mechanisms in chemistry a joke.

secondary amine with a keytone yields an enamine. just remember that forever. in primary we just remove an H2O. this is all you will ever need. i never do mechanisms, to me those are a joke/huge waste of time. orgo is just tricks. if you have any other questions on rxns feel free to pm me, ill help you to the best of my ability.

 

[ajhalls3]

I see 3 carbon groups attached to that nitrogen where he is pointing.... Your purple circle is not what he is talking about but part of the substrate to get to the product.

 

[AllahIsGreater]

I agree that you dont need to know every mech for the DAT - but it's foolish to call mechanisms in chemistry a joke.

lol idk man for me they are a joke. but then again i am one of those people who thinks anyone can do well in orgo, for me its just memorization. just depends on how u teach urself i guess. i never look at mechanisms ever. just make up ur own rules. it works for me 🙂

 

[Cofo]

lol idk man for me they are a joke. but then again i am one of those people who thinks anyone can do well in orgo, for me its just memorization. just depends on how u teach urself i guess. i never look at mechanisms ever. just make up ur own rules. it works for me 🙂

The stars are made up of condensed smoke that came from burning trash in Paddy's Bar (It's Always Sunny lovers will get this reference). I just make up my own rules (my own understanding). it works for me 🙂

Well, I'm glad it works for you dude lol...just personally, i want to actually have a true understanding of this mechanism.

 

[Cofo]

I see 3 carbon groups attached to that nitrogen where he is pointing.... Your purple circle is not what he is talking about but part of the substrate to get to the product.

AJ, where are you seeing a third alkyl group (third carbon) attached to the nitrogen?
I see 2 carbons, 1 lone pair, and 1 Hydrogen in the purple circle that i drew.
Even LOOK AT THE PRINTOUT that you get from the videos...it says its a Secondary amine, implying 2 carbons, not 3.

 

[ddslee]

i'm confused...why would one of the alpha carbons get deprotonated....since Chad's nucleophile DOES have a hydrogen directly bonded to it?

I hope this help...

 

[Cofo]

I hope this help...

👍👍👍
Thank you so much, I understand it now. You rock.