When dealing with electrophilic aromatic substitutions, fluorine was a weaker electron withdrawing group than chlorine and bromine, making EAS faster for fluorobenzene than for chloro/bromobenzene. This was explained by the weaker back bonding of the large chlorine and bromine atoms compared to fluorine. However, when dealing with nucleophilic aromatic substitutions, for some reason fluorine becomes more electron withdrawing than the other 2 atoms. Why is that?



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