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Why do we need to add FeBr3 for bromination of anisole, but not for bromination of phenol?
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Milan Woodson
Why do we need to add FeBr3 for bromination of anisole, but not for bromination of phenol?
I don't think polarization is the issue. Adding $\ce{FeBr3}$ is just to reduce the $\ce{Br-Br}$ bond strength, speeding up the reaction (attack of the aromatic ring on the bromine is part of the rate determining step, which is slow in the bromination of benzene). It functions as a catalyst being recycled when the $\ce{Br-}$ grabs a $\ce{H+}$ to restore aromaticity in the ring. I'm pretty sure — at least I see no reason to doubt — that the catalyst requirements for the bromination of anisole and the bromination of phenol do not differ much, if at all. That is, no catalyst is required for the bromination of anisole.
I don't think polarization is the issue. Adding $\ce{FeBr3}$ is just to reduce the $\ce{Br-Br}$ bond strength, speeding up the reaction (attack of the aromatic ring on the bromine is part of the rate determining step, which is slow in the bromination of benzene). It functions as a catalyst being recycled when the $\ce{Br-}$ grabs a $\ce{H+}$ to restore aromaticity in the ring. I'm pretty sure — at least I see no reason to doubt — that the catalyst requirements for the bromination of anisole and the bromination of phenol do not differ much, if at all. That is, no catalyst is required for the bromination of anisole.
@ag_dhruv I agree, but that is exactly what I said? The $\ce{Br+}$ is not present as a lose species, it would be too unstable. Im also not that big of a fan of UC Davis website. It contains plenty of incomplete (and erroneous) material. Cheers :)More
Um, as far as I know, FeBr3 is actually used to generate an electrophile. It grabs one Br atom from the Br2 molecule and gives us Br+, which is an electrophile. This make it easier for it to under bromination. Refer to this : More
I don't think polarization is the issue. Adding $\ce{FeBr3}$ is just to reduce the $\ce{Br-Br}$ bond strength, speeding up the reaction (attack of the aromatic ring on the bromine is part of the rate determining step, which is slow in the bromination of benzene). It functions as a catalyst being recycled when the $\ce{Br-}$ grabs a $\ce{H+}$ to restore aromaticity in the ring. I'm pretty sure — at least I see no reason to doubt — that the catalyst requirements for the bromination of anisole and the bromination of phenol do not differ much, if at all. That is, no catalyst is required for the bromination of anisole.
I don't think polarization is the issue. Adding $\ce{FeBr3}$ is just to reduce the $\ce{Br-Br}$ bond strength, speeding up the reaction (attack of the aromatic ring on the bromine is part of the rate determining step, which is slow in the bromination of benzene). It functions as a catalyst being recycled when the $\ce{Br-}$ grabs a $\ce{H+}$ to restore aromaticity in the ring. I'm pretty sure — at least I see no reason to doubt — that the catalyst requirements for the bromination of anisole and the bromination of phenol do not differ much, if at all. That is, no catalyst is required for the bromination of anisole.
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