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

Answer 1

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.

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Answer 2

Xavier Avery

Chlorine substitution on a phenyl ring can modify the reactivity of the ring by influencing the electron density distribution. Chlorine is an electron-withdrawing group, which means it pulls electron density away from the phenyl ring through its electronegativity. This decreases the electron density around the ring, making it less reactive towards electrophilic aromatic substitution reactions. Additionally, the presence of chlorine can also direct the regioselectivity of further substitution reactions on the phenyl ring.

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Answer from HIX Tutor

When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.