(i) In Friedel–Crafts reaction, AlCl3 is added as a catalyst which is a Lewis acid. It forms a salt with aniline due to which the nitrogen of aniline acquires positive charge. This positively charged nitrogen acts as a strong deactivating group, hence aniline does not undergo Friedel– Crafts reaction.
(ii) The ammonolysis of alkyl halides with ammonia is a nucleophilic substitution reaction in which ammonia acts as a nucleophile by donating the electron pair on nitrogen atom to form primary amine as the initial product. Now, the primary amine can act as a nucleophile and combine with alkyl halide (if available) to give secondary amine and the reaction continues in the same way to form tertiary amine and finally quaternary ammonium salt. Thus, a mixture of products is formed and it is not possible to separate individual amines from the mixture.
