Question

Explain why the nucleophilic substitution reaction of aryl halide is difficult and takes place under drastic conditions?

Answer 1

Aryl halides are relatively unreactive toward nucleophilic substitution reactions. This lack of reactivity is due to several factors. Steric hindrance caused by the benzene ring of the aryl halide prevents S N2 reactions. Likewise, phenyl cations are unstable, thus making S N1 reactions impossible.

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Answer 2

Answer:

Aryl halides are relatively unreactive toward nucleophilic substitution reactions. This lack of reactivity is due to several factors. Steric hindrance caused by the benzene ring of the aryl halide prevents S N2 reactions. Likewise, phenyl cations are unstable, thus making S N1 reactions impossible. In addition, the carbon‐halogen bond is shorter and therefore stronger in aryl halides than in alkyl halides. The carbon‐halogen bond is shortened in aryl halides for two reasons. First, the carbon atom in aryl halides is sp 2 hybridized instead of sp 3 hybridized as in alkyl halides. Second, the carbon‐halogen bond has partial double bond characteristics because of resonance.

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