Friedel-Crafts alkylation necessitates an electrophilic aromatic substrate. Aniline does not undergo Friedel-Crafts alkylation. This is due to the strong activation of the benzene ring by the amino group (-\(NH_2\)), which leads to excessive reactivity, hindering reaction control. Additionally, the lone electron pair on aniline's nitrogen atom forms a complex with Lewis acid catalysts (e.g., \(AlCl_3\)), deactivating the ring and inhibiting alkylation. The carbylamine test yields a positive result for primary amines, and aniline, being a primary amine, will consequently produce a positive test.
The correct order of the rate of reaction of the following reactants with nucleophile by \( \mathrm{S_N1} \) mechanism is:
(Given: Structures I and II are rigid) 