How does chlorine substitution on a phenyl ring modify the reactivity of the ring?

1 Answer
Apr 1, 2016

Because the electronegative chlorine atom withdraws electron density from the ring, making the ring less nucleophilic.


So, by induction, the chloro-substituted phenyl ring is a less powerful nucleophile, and thus, less likely to undergo substitution by electrophiles. Because of the lone pairs on the chloride, it is an #"ortho"# and #"para"# director in those reactions where it does undergo substitution.