Why does the arenium ion intermediate (Wheland intermediate) possess a substantial positive charge distribution over the remaining five hybridized carbon atoms, rather than localizing the positive cha

Question

Why does the arenium ion intermediate (Wheland intermediate) possess a substantial positive charge distribution over the remaining five $sp^2$ hybridized carbon atoms, rather than localizing the positive charge entirely on the carbon adjacent to the site of attack?

Prashant Kotian · Accepted Answer

Correct answer: A. Once the electrophile attacks, one carbon becomes hybridized. The remaining five -orbitals remain conjugated. The 4 remaining electrons are delocalized across these five -orbitals, effectively spreading the positive charge over the ortho and para positions relative to the carbon, generating 3 primary resonance structures.

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