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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!

Reply 1

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 1 year ago)

Reply 2

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?

Reply 3

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

Reply 4

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

Reply 5

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?

Reply 6

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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