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The big fluffy d electrons of iodine allow that molecule to have a cyclo-iodonium ion resonance structure which reacts with bromine in a polar fashion and the Br- generated can attack the other 2 position maybe. My idea felt like a Payne rearrangement with a bunch of halides
I have to admit this reaction was a bit too complex for me, too many proton transfers 😅 As for the next week's reaction, the first steps is the electrophilic addition of bromine to the alkene, forming a bromonium intermediate which will open by attack of the remaining bromide, leading to the 1,2.dibromo compound. This will happen in the opposite face of the iodine group due to its huge size. Then, the central bromo group will form a new bromonium ring by kicking the iodine atom, which will open this ring through the central carbon in the opposite face of both bromine atoms. This leads to the product with correct stereochemistry, which is more stable thanks to the alternating halides, which minimizes steric hindrance 😄😄😄
Maybe we can predict here, as a cyclic ketone in fairly acidic may form a carboxylic and since same molecule has hydroxyl, it will undergo esterification which occurs usually in acidic medium.
Ngl heterocycle cascade mechanisms are more fun to figure out than organometallics, including photoredox type couplings but they’re still fun in the aspects that some side products still form and have to be rationalised I unfortunately do not know much about organometallics
Haha! You’re definitely not alone in that. There’s a whole other world of reactivity to explore in organometallic chemistry. I’m an organometallic chemist so I’m biased but I agree mechanisms are more fun in traditional organic chemistry - more well understood as well!
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
So clear - pls keep making these!
Thanks so much, Henry! I appreciate the kind words!
Very interesting mechanism! Thank you for showing it to us. As always, looking forward to Mondays. :)
Ayyy! So glad to hear that. Thank you!
Excellent explaination
Thank you so much!
The big fluffy d electrons of iodine allow that molecule to have a cyclo-iodonium ion resonance structure which reacts with bromine in a polar fashion and the Br- generated can attack the other 2 position maybe. My idea felt like a Payne rearrangement with a bunch of halides
Might steal that Payne rearrangement for a future video! 😉
I have to admit this reaction was a bit too complex for me, too many proton transfers 😅 As for the next week's reaction, the first steps is the electrophilic addition of bromine to the alkene, forming a bromonium intermediate which will open by attack of the remaining bromide, leading to the 1,2.dibromo compound. This will happen in the opposite face of the iodine group due to its huge size. Then, the central bromo group will form a new bromonium ring by kicking the iodine atom, which will open this ring through the central carbon in the opposite face of both bromine atoms. This leads to the product with correct stereochemistry, which is more stable thanks to the alternating halides, which minimizes steric hindrance 😄😄😄
Absolutely crushed it for next week, which I would actually argue is more difficult than this week!
Did not get this one but what an impressive reaction (I was close though) ! Can't wait to see the next one !
The next 2 have relatively similar pathways so see if you can use them as an opportunity to learn some new reactivity!
Maybe we can predict here, as a cyclic ketone in fairly acidic may form a carboxylic and since same molecule has hydroxyl, it will undergo esterification which occurs usually in acidic medium.
Ngl heterocycle cascade mechanisms are more fun to figure out than organometallics, including photoredox type couplings but they’re still fun in the aspects that some side products still form and have to be rationalised
I unfortunately do not know much about organometallics
Haha! You’re definitely not alone in that. There’s a whole other world of reactivity to explore in organometallic chemistry. I’m an organometallic chemist so I’m biased but I agree mechanisms are more fun in traditional organic chemistry - more well understood as well!
Missing a carbon atom in the structure drawn in cyan at 3:00. But cute.