How did you do? I'd love to hear your proposals for next week's mechanism so drop them down below! Subscribe for more chemistry content, and hit the notification bell to stay updated! #ScienceCommunity #MechanismMonday #OrganicChemistry
Thanks! I love that you thought it about it on your own and basically checked your answer with the video! That’s the best way to learn, in my opinion! Always appreciate your comments!
For next weeks mechanism 1. Primary amine kicks off the Cl forming a secondary amine with the epoxide hanging off of it 2. The last hydrogen on the secondary amine might be hydrogen bonding with the epoxide (5 member pseudo-ring) allowing it to undergo markovnikov type substitution (even though its basic conditions) with the carbonate anion as a nucleophile 3. Nitrogen attacks the carbonate carbon kicking off an OH with some proton transfer happening 4. Work up with acid and voila maybe?
Better late then never! The amine attacks the epoxide at the least substituted position, then the alkoxide intermediate kicks off the chlorine forming another epoxide ring. The chloride then deprotonates the amine forming HCl. This protonates the potassium carbonate which generates CO2 in situ. The amine then attacks the CO2 forming a carbamate anion. Anion picks up a proton from the amine to make every thing neutral. Then the epoxide is protonated by the carbamic acid. This opens the ring and gives a positive charge on the most substituted position of the epoxide. Which then carbamate dumps its electrons into the carbocation forming our final product.
@@abs0lute-zer061 Solution is up. I think you'll be surprised by the first step. We actually do a similar reaction in our labs at GT and most students initially expect epoxide opening to occur first.
@rojaslab neither way I feel like is wrong. But in my synthesis lab, we were synthesizing propranolol from 1-napthol and epichlorohydrin. My professor showed the mechanism with the ring opening and then kicking off the chlorine. So I guess it stuck lol
How did you do? I'd love to hear your proposals for next week's mechanism so drop them down below! Subscribe for more chemistry content, and hit the notification bell to stay updated! #ScienceCommunity #MechanismMonday #OrganicChemistry
Didn't get this one (almost however), thanks for explaining the mechanism so well ! Hope the serie continues
Thanks! I love that you thought it about it on your own and basically checked your answer with the video! That’s the best way to learn, in my opinion! Always appreciate your comments!
Thank you!! you’re videos are great for people like me who don’t study chem in college but love it! Keep up the amazing work!!
Thanks so much for saying that! It means a lot to me and I’m glad you’re enjoying them!
For next weeks mechanism
1. Primary amine kicks off the Cl forming a secondary amine with the epoxide hanging off of it
2. The last hydrogen on the secondary amine might be hydrogen bonding with the epoxide (5 member pseudo-ring) allowing it to undergo markovnikov type substitution (even though its basic conditions) with the carbonate anion as a nucleophile
3. Nitrogen attacks the carbonate carbon kicking off an OH with some proton transfer happening
4. Work up with acid and voila maybe?
A! You’re a star! That’s an excellent proposal!
Better late then never!
The amine attacks the epoxide at the least substituted position, then the alkoxide intermediate kicks off the chlorine forming another epoxide ring. The chloride then deprotonates the amine forming HCl. This protonates the potassium carbonate which generates CO2 in situ. The amine then attacks the CO2 forming a carbamate anion. Anion picks up a proton from the amine to make every thing neutral. Then the epoxide is protonated by the carbamic acid. This opens the ring and gives a positive charge on the most substituted position of the epoxide. Which then carbamate dumps its electrons into the carbocation forming our final product.
Ayyy just in the nick of time, I’d say! The CO2 part, That’s a really clever idea!
@rojaslab I suppose we'll see tomorrow haha
@@abs0lute-zer061 Solution is up. I think you'll be surprised by the first step. We actually do a similar reaction in our labs at GT and most students initially expect epoxide opening to occur first.
@rojaslab neither way I feel like is wrong. But in my synthesis lab, we were synthesizing propranolol from 1-napthol and epichlorohydrin. My professor showed the mechanism with the ring opening and then kicking off the chlorine. So I guess it stuck lol
Do you make these videos because for the sole purpose of education?
Yeah! Many of them, I use for my own real classes I teach at Georgia Tech, and for the love of chemistry!
@@rojaslab that's fantastic, the work you're doing is necessary, and a public good. Thank you for making it available