Loading VerChem
Preparing your chemistry tools...
Preparing your chemistry tools...
Also known as: EAS, SEAr
The characteristic reaction of aromatic rings: an electrophile replaces a hydrogen on the ring while preserving aromaticity. The mechanism involves formation of a non-aromatic carbocation intermediate (arenium ion/sigma complex) followed by deprotonation to restore aromaticity.
Generation of the electrophile (E⁺), often with a Lewis acid catalyst. Example: Br₂ + FeBr₃ → Br⁺ + FeBr₄⁻.
Lewis acid activates the electrophile
The π electrons of the aromatic ring attack the electrophile, forming the arenium ion (sigma complex). Aromaticity is temporarily lost.
Slow step — rate determining
A base removes a proton from the sp³ carbon of the arenium ion, restoring aromaticity. This is fast because aromaticity is highly stabilizing.
Fast step — aromaticity restored
Benzene
Br₂, FeBr₃
Bromobenzene
Toluene
HNO₃, H₂SO₄
o-Nitrotoluene + p-Nitrotoluene
Benzene
HNO₃, H₂SO₄
Nitrobenzene
The most important reaction class for building substituted aromatic compounds. Foundation of pharmaceutical and materials chemistry.