All your observations are correct.But one thing you seem to be missing is the presence of vacant d orbitals in Chlorine.I am sorry but I couldn't find pictures as such but I am sure you will understand after drawing out the resonance structures.
So when the lone pair on oxygen is delocalized and is at para position,then the d orbital of chlorine can "take up" and stabilize the compund.Flourine can't do the same.
All your observations are correct.But one thing you seem to be missing is the presence of vacant d orbitals in Chlorine.I am sorry but I couldn't find pictures as such but I am sure you will understand after drawing out the resonance structures.
So when the lone pair on oxygen is delocalized and is at para position,then the d orbital of chlorine can "take up" and stabilize the compund.Flourine can't do the same.
@Karan Singh If it was at the ortho position then I would have agreed but at such a long distance it doesnt seem very accurate.More
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Order of -I in Halogens is −F > −Cl > −Br > −I
Order of +M in Halogens is −F > −Cl > −Br > −I
So whenever halogens are in resonance (as in p-fluorophenol and p-chlorophenol), we take combined effect as:
−F < −Cl < −Br < −I
and consider halogens as an overall EWG.
Hence, p-chlorophenol is more acidic than p-fluorophenol.
Order of -I in Halogens is −F > −Cl > −Br > −IOrder of +M in Halogens is −F > −Cl > −Br > −I
So whenever halogens are in resonance (as in p-fluorophenol and p-chlorophenol), we take combined effect as:−F < −Cl < −Br < −Iand consider halogens as an overall EWG.
Hence, p-chlorophenol is more acidic than p-fluorophenol.
This is a wrong answer, your second line contradicts itself. Halogens are considered overall as electron-withdrawing groups. Right. Then the withdrawing effect is inductive effect, so shouldnt the order of -I in halogens be considered, giving F > Cl? Think it over. Also, when you answer, including a source, from a good textbook or online resource, is a great idea.More
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This is due to the fact that we also consider +M effect . In fluorine it’s 2p orbital that participated in overlapping but in chlorine it’s 3 p orbital. 3p of chlorine does not overlap efficiently with 2p of benzene carbon so +m decreases in chlorine thus acidic nature increases
This is due to the fact that we also consider +M effect . In fluorine it’s 2p orbital that participated in overlapping but in chlorine it’s 3 p orbital. 3p of chlorine does not overlap efficiently with 2p of benzene carbon so +m decreases in chlorine thus acidic nature increases
All your observations are correct.But one thing you seem to be missing is the presence of vacant d orbitals in Chlorine.I am sorry but I couldn't find pictures as such but I am sure you will understand after drawing out the resonance structures.
So when the lone pair on oxygen is delocalized and is at para position,then the d orbital of chlorine can "take up" and stabilize the compund.Flourine can't do the same.
All your observations are correct.But one thing you seem to be missing is the presence of vacant d orbitals in Chlorine.I am sorry but I couldn't find pictures as such but I am sure you will understand after drawing out the resonance structures.
So when the lone pair on oxygen is delocalized and is at para position,then the d orbital of chlorine can "take up" and stabilize the compund.Flourine can't do the same.
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Order of -I in Halogens is −F > −Cl > −Br > −I Order of +M in Halogens is −F > −Cl > −Br > −I
So whenever halogens are in resonance (as in p-fluorophenol and p-chlorophenol), we take combined effect as: −F < −Cl < −Br < −I and consider halogens as an overall EWG.
Hence, p-chlorophenol is more acidic than p-fluorophenol.
Order of -I in Halogens is −F > −Cl > −Br > −IOrder of +M in Halogens is −F > −Cl > −Br > −I
So whenever halogens are in resonance (as in p-fluorophenol and p-chlorophenol), we take combined effect as:−F < −Cl < −Br < −Iand consider halogens as an overall EWG.
Hence, p-chlorophenol is more acidic than p-fluorophenol.
More
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This is due to the fact that we also consider +M effect . In fluorine it’s 2p orbital that participated in overlapping but in chlorine it’s 3 p orbital. 3p of chlorine does not overlap efficiently with 2p of benzene carbon so +m decreases in chlorine thus acidic nature increases
This is due to the fact that we also consider +M effect . In fluorine it’s 2p orbital that participated in overlapping but in chlorine it’s 3 p orbital. 3p of chlorine does not overlap efficiently with 2p of benzene carbon so +m decreases in chlorine thus acidic nature increases
More
VOTE