In Friedel-Crafts alkylation of aniline, one gets:

In Friedel-Crafts alkylation of aniline, one gets:
  1. alkylated product with ortho and para substitution.
  2. secondary amine after acidic treatment.
  3. an amide product.
  4. positively charged nitrogen at benzene ring.

Solution

Aniline does not undergo Friedel-crafts reaction due to salt formation with aluminium chloride, the Lewis acid, which is used as a catalyst, whereas aniline is a strong base. So, an acid-base reaction will take place. Thus, aniline reacts with AlCl3 to form a salt.

Due to the positive charge on the nitrogen atom (shows -I effect and it is meta directing), electrophilic substitution in the benzene ring is deactivated. Hence, the Friedel-Crafts reaction will not take place in aniline.

Asked in: JEE Main 2022 (29 Jun Shift 2)

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