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
I love pericyclic reactions, especially DIels-Alder, because how efficient and beautiful to draw they are. For the next reaction, the mitrile is hydrolyzed to a carboxylic acid, which then forms the lactone. For this hydrolysis, the acid protonates the nitrogen, making the carbon highly electrophilic. Here, a water molecule could attack the nitrile and form a C-OH and a C=NH bond; however, the intramolecular attack of the alcohol is probably more favored here. Then, the imine bond is hydrolyzed to a carbonyl (protonation of nitrogen, attack from water, proton transfer and removal of ammonia), which eventually forms the lactone.
Great analysis for next week. For pericycloc reactions, I’ve gotta be honest: in my younger years, I loathed them. I thought they were useless in most real world cases. Time has brought me the maturity to see that not everything requires palladium to be cool!
For next week, after protonation of nitrile we have an intramolecular nucleophilic attack from the alcohol, then hydrolysis of the resulting imine yields the product
Hello! I have a proposal for next weeks reaction. Hydrolysis of the cyano group will lead to formation of a carboxylic acid . And then the acid and alcohol groups undergo esterification reaction to produce a ester (I think its a lactone in this case)
@@rojaslabthen the alcohol just attacks the carbon and further attacks from water would directly produce the ester? Dang why am I always taking the long paths 😂
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
I love pericyclic reactions, especially DIels-Alder, because how efficient and beautiful to draw they are.
For the next reaction, the mitrile is hydrolyzed to a carboxylic acid, which then forms the lactone. For this hydrolysis, the acid protonates the nitrogen, making the carbon highly electrophilic. Here, a water molecule could attack the nitrile and form a C-OH and a C=NH bond; however, the intramolecular attack of the alcohol is probably more favored here. Then, the imine bond is hydrolyzed to a carbonyl (protonation of nitrogen, attack from water, proton transfer and removal of ammonia), which eventually forms the lactone.
Great analysis for next week. For pericycloc reactions, I’ve gotta be honest: in my younger years, I loathed them. I thought they were useless in most real world cases. Time has brought me the maturity to see that not everything requires palladium to be cool!
Super underrated channel holly
Ayyy thanks for the kind words! 🫡
neat mechanism! i really like diels alder reactions
I had a professor in graduate school who LOVED them! I always hated them but age has made me see the beauty 😂
For next week, after protonation of nitrile we have an intramolecular nucleophilic attack from the alcohol, then hydrolysis of the resulting imine yields the product
You and I are on the same wavelength! Bravo 👏🏾
for next week, hydrolysis of nitrile via amide then to RCOOH, followed by fischer esterification
I like the thought process but I actually think it’s simpler than that. Think what might happen if you protonate the nitrile. What might happen next?
@rojaslab the alcohol can directly attack as a nucleophile perhaps
@@real_nitrobenzene Nice work!
Pinner reaction for next week
A classic! How’d you know the name?
Hello!
I have a proposal for next weeks reaction.
Hydrolysis of the cyano group will lead to formation of a carboxylic acid . And then the acid and alcohol groups undergo esterification reaction to produce a ester (I think its a lactone in this case)
I love the way you’re thinking! I actually think it’s simpler than that though. If you protonate the nitrile, what might happen next?
@@rojaslabthen the alcohol just attacks the carbon and further attacks from water would directly produce the ester?
Dang why am I always taking the long paths 😂
@@milind774 haha keep in mind that I only know the shorter path because I've worked on a video for it. None of us are perfect!
Wtf?? The first reagent is not a byciclo
Time stamp? Because he said bicyclic indicating two ring system which the product is.
I believe the technical term is “bridged bicyclic.” But I’m just a guy on the internet so who knows? 🤷🏿♂️
The core skeleton of the first product is a [2.2.1] bicyclic ring with an oxygen bridge.