Halogens act as anomalous substituents on the benzene ring. Despite being highly electronegative, th — Aromatic Hydrocarbons Chemistry Question

💡 Solution & Explanation

Halogens are unique because they have a strong inductive electron-withdrawing effect ($-I$) which reduces the overall electron density of the ring, making the reaction slower than benzene (deactivating). However, when electrophilic attack occurs, the lone pairs on the halogen can participate in resonance ($+M$), forming a stable halonium-like intermediate that specifically stabilizes the ortho and para transition states.