reaction between chlorobenzene and sodium methoxide in presence of cupric salts
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Chlorobenzene is inert towards most forms of nucleophilic substitution. In particular:
A SN1SN1 mechanism is not likely here because the carbon is sp2sp2 hybridised, the C−ClC−Clbond is strong, and the dissociation of Cl−ClX− is therefore not very likely.SN2SN2 substitution doesn't occur because 1) the C−ClC−Cl bond is strong 2) the σ∗σ∗ orbital is in the middle of the ring and is inaccessible to a nucleophile.The SNArSNAr mechanism could be followed if there is an electron-withdrawing grouportho or para to the chlorine atom, but in chlorobenzene, there is no such EWG. This reaction is well-documented with both NaOHNaOH and NaNH2NaNHX2. I don't have the time to look if it's been done with NaOMeNaOMe, but I strongly believe that it does happen this way.
A SN1SN1 mechanism is not likely here because the carbon is sp2sp2 hybridised, the C−ClC−Clbond is strong, and the dissociation of Cl−ClX− is therefore not very likely.SN2SN2 substitution doesn't occur because 1) the C−ClC−Cl bond is strong 2) the σ∗σ∗ orbital is in the middle of the ring and is inaccessible to a nucleophile.The SNArSNAr mechanism could be followed if there is an electron-withdrawing grouportho or para to the chlorine atom, but in chlorobenzene, there is no such EWG. This reaction is well-documented with both NaOHNaOH and NaNH2NaNHX2. I don't have the time to look if it's been done with NaOMeNaOMe, but I strongly believe that it does happen this way.
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