Question

Answer the following questions:  

a. Aniline does not undergo Friedel Crafts reactions.

b. Although -NH2 is an ortho-para directing group, nitration of aniline produces 47% meta substituted product.  

c. Aniline cannot be prepared by Gabriel pthalimide synthesis.

Answer 1

a) Aniline does not undergo Friedel Craft acylation or alkylation. This is due to salt formation between base i.e., aniline and Lewis acid i.e., anhydrous AlCl3 used as octalyst in the reaction. Due to this, nitrogen of aniline acquires positive charge and thus acts as a strong deactivating group.

c) Gabriel's synthesis can not prepare aniline. Using this process, aniline can not be prepared, because aryl halides do not undergo nucleophilic substitution with the phthalimide-formed anion.