electron-withdrawing groups

Electron-withdrawing groups act as both meta-directors and deactivators in the electrophilic aromatic substitution (EAS reaction). Carbonyl groups, in which the carbonyl is directly attached to the aromatic ring, are very common EWGs. The polarized carbonyl has a partial positive charge on the carbonyl carbon. The partial positive on carbon destabilizes the intermediates that lead to ortho and para substitution, so the meta product is favored. Because EWGs pull electron density from the ring, they also cause the ring to be less reactive as a nucleophile. Other common EWGs include nitriles and nitro groups.

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