Why does nitrobenzene fail to undergo Fieldel-Crafts alkylation with tert-butyl chloride and AlCl₃?

Question

Quizplus · Accepted Answer

Nitrobenzene is a poor nucleophile and cannot act as a strong electrophile in the Fieldel-Crafts alkylation reaction. The nitro group is a strong electron withdrawing group, which makes the benzene ring less susceptible to electrophilic attack. Therefore, the reaction is unlikely to occur with tert-butyl chloride and AlCl3. The tert-butyl cation is actually a good electrophile due to the presence of electron-withdrawing groups on the carbon atom, but the poor nucleophilicity of nitrobenzene prevents the reaction from taking place.

Why Does Nitrobenzene Fail to Undergo Fieldel-Crafts Alkylation with Tert-Butyl