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chemistry question organic

hi, please could i have help on part iv of this question? I thought there would be Br2 added onto the benzene ring, in the 2 and 4th position but the ms says this is wrong?
Here is the question: https://ibb.co/vqJbbBJ
Thanks!
Original post by anonymous56754
hi, please could i have help on part iv of this question? I thought there would be Br2 added onto the benzene ring, in the 2 and 4th position but the ms says this is wrong?
Here is the question: https://ibb.co/vqJbbBJ
Thanks!

It should add to the 3 (meta-) position rather than the 2 (ortho-) and 4 (para-) positions, since the carbonyls attached to the ring are electron-withdrawing and so make the 2 and 4 positions less electron-dense, hence they are less susceptible to electrophilic attack.

If you have covered resonance structures in your studies, they may be worth recapping. If not, then I have no clue why they are even bothering trying to explain arene directing effects.

Edit: technically speaking the 4 positions (relative to one carbonyl) are also the 3 positions (relative to the second carbonyl), so it's probably better to just refer to the 2 and 3 positions in this case. Apologies for the dubious explanation.
(edited 2 months ago)
Original post by TypicalNerd
It should add to the 3 (meta-) position rather than the 2 (ortho-) and 4 (para-) positions, since the carbonyls attached to the ring are electron-withdrawing and so make the 2 and 4 positions less electron-dense, hence they are less susceptible to electrophilic attack.
If you have covered resonance structures in your studies, they may be worth recapping. If not, then I have no clue why they are even bothering trying to explain arene directing effects.
Edit: technically speaking the 4 positions (relative to one carbonyl) are also the 3 positions (relative to the second carbonyl), so it's probably better to just refer to the 2 and 3 positions in this case. Apologies for the dubious explanation.

thank you, sorry i didn't recognise it was carbonyl. But in the ms, it says there are no Br atoms on the benzene ring, I'm not sure why not?
Original post by anonymous56754
thank you, sorry i didn't recognise it was carbonyl. But in the ms, it says there are no Br atoms on the benzene ring, I'm not sure why not?

Then I would guess it preferentially attacks the alkene. Since carbonyl groups are electron-withdrawing, they make the arene less electron-dense and so less reactive towards electrophiles like bromine
Original post by TypicalNerd
Then I would guess it preferentially attacks the alkene. Since carbonyl groups are electron-withdrawing, they make the arene less electron-dense and so less reactive towards electrophiles like bromine

Also, there was no mention of heating or a halogen carrier. With an arene even less reactive than benzene (due to the electron-withdrawing effects of the carbonyls bonded to the ring), you’d no doubt beed both
Original post by TypicalNerd
Also, there was no mention of heating or a halogen carrier. With an arene even less reactive than benzene (due to the electron-withdrawing effects of the carbonyls bonded to the ring), you’d no doubt beed both

sorry, what do you mean by halogen carrier?
Original post by anonymous56754
sorry, what do you mean by halogen carrier?


It’s just the term for any catalyst used in halogenating an arene, e.g AlBr3, FeBr3

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