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Multiple Choice

Benzene can undergo which type of reaction, according to classic aromatic chemistry?

Benzene’s ring is stabilized by a delocalized π electron system, which makes reactions that keep the ring aromatic highly favorable. In electrophilic aromatic substitution, the ring temporarily forms a nonaromatic intermediate, but deprotonation quickly restores the aromatic system, yielding a substituted benzene. This pathway preserves aromatic stability, so benzene readily undergoes substitution rather than adding to the ring, polymerizing, or doing nothing under normal conditions. Classic examples include nitration, halogenation, and Friedel–Crafts alkylation/acylation, all of which replace a hydrogen with an electrophile while maintaining the aromatic framework.

Benzene’s ring is stabilized by a delocalized π electron system, which makes reactions that keep the ring aromatic highly favorable. In electrophilic aromatic substitution, the ring temporarily forms a nonaromatic intermediate, but deprotonation quickly restores the aromatic system, yielding a substituted benzene. This pathway preserves aromatic stability, so benzene readily undergoes substitution rather than adding to the ring, polymerizing, or doing nothing under normal conditions. Classic examples include nitration, halogenation, and Friedel–Crafts alkylation/acylation, all of which replace a hydrogen with an electrophile while maintaining the aromatic framework.