First a claisen condensation reaction takes place which forms a bicyclic intermediate and the loss of ethanol. Then the acidic alpha hydrogen, in the middle of the two carbonyls, is deprotonated forming a new alkene that breaks the C-C bridge. The electrons from the broken bond moves towards the carbonyl that was once an ethyl ester. This creates the six membered ring and the alkoxide giving the final product.
I really enjoy these videos but it’s really disappointing if one can’t get to the right solution because the starting material was drawn incorrectly. The double bond was missing in the first figure. Are the double bonds correct in the product of the new exercise? If I draw the mechanism with a ring opening of the formed [2.2.0]-bicyclohexanone I get the double bonds in different positions
Hi Robin! Like most people, I’ve definitely made mistakes in my past. However, this go around I believe everything is correct and I’d encourage you to check again! Importantly for your double bonds on the 2nd one, it may be possible that your resonance structure is energetically equivalent, even if not identical!
Yeaaah mechanism monday 🕺
Haha! Love it! 💃🏼
Your clip is pretty interesting. Because of busy schedule, i could not watch fully but i still liked. Hope you successfull
Ayyy I appreciate the engagement for the UA-cam algorithm! You’re the best!
First a claisen condensation reaction takes place which forms a bicyclic intermediate and the loss of ethanol. Then the acidic alpha hydrogen, in the middle of the two carbonyls, is deprotonated forming a new alkene that breaks the C-C bridge. The electrons from the broken bond moves towards the carbonyl that was once an ethyl ester. This creates the six membered ring and the alkoxide giving the final product.
Ayyyy you love to see it! Absolutely crushed it!
I really enjoy these videos but it’s really disappointing if one can’t get to the right solution because the starting material was drawn incorrectly. The double bond was missing in the first figure.
Are the double bonds correct in the product of the new exercise? If I draw the mechanism with a ring opening of the formed [2.2.0]-bicyclohexanone I get the double bonds in different positions
Hi Robin! Like most people, I’ve definitely made mistakes in my past. However, this go around I believe everything is correct and I’d encourage you to check again! Importantly for your double bonds on the 2nd one, it may be possible that your resonance structure is energetically equivalent, even if not identical!
I thought it was a Diels-Alder Mechanism and tried everything but it obviously didnt work. Makes sense how you solved it.
I get these wrong all the time, which is why I think they’re so fun! We’re just sharpening our skills!