Benzene undergoes electrophilic substitution reactions rather than nucleophilic substitution reactions due to its high stability resulting from aromaticity. The electron density in the π cloud of benzene is spread evenly across all six carbon atoms, forming a stable aromatic system.
In electrophilic substitution reactions, an electrophile (electron-seeking species) attacks the electron-rich benzene ring. The pi electrons are readily available for bonding with the electrophile, and the resulting intermediate is stabilized by the aromatic character of benzene.
On the other hand, nucleophilic substitution reactions typically involve the replacement of a leaving group by a nucleophile. However, benzene's stability makes it less prone to nucleophilic attacks, as breaking the aromatic system would require significant energy input.
In summary, the high stability arising from aromaticity in benzene favors electrophilic substitution reactions over nucleophilic substitution reactions.
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