Halogens (like and ) act as anomalous substituents on the benzene ring. They are overall deactivating groups, yet they direct incoming electrophiles to the ortho and para positions. What explains this

Question

Halogens (like $-Cl$ and $-Br$) act as anomalous substituents on the benzene ring. They are overall deactivating groups, yet they direct incoming electrophiles to the ortho and para positions. What explains this dual behavior?

Prashant Kotian · Accepted Answer

Correct answer: C. Halogens withdraw electron density inductively (), deactivating the overall ring. However, during electrophilic attack, their lone pairs form halonium-like double bonds () that specifically stabilize the ortho and para transition states.

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