Question

Given below are two statements:
Statement I: Aniline does not undergo Friedel-Crafts alkylation reaction.
Statement II: Aniline cannot be prepared through Gabriel synthesis.
In the light of the above statements, choose the correct answer from the options given below

• A. Both Statement I and Statement II are true.
• B. Both Statement I and Statement II are false.
• C. Statement I is correct but Statement II is false.
• D. Statement I is incorrect but Statement II is true

Answer 1

The Correct Option is A

Aniline, a primary aromatic amine, indeed does not undergo the Friedel-Crafts alkylation reaction. The reason for this lies in the neutralization of the Lewis acid catalyst (such as AlCl₃) used in the Friedel-Crafts reaction by the lone pair of electrons on the nitrogen atom of aniline, forming a complex that deactivates the catalyst. Hence, Statement I is true.

Regarding Statement II, Gabriel synthesis is a method used to prepare primary amines from alkyl halides. In the Gabriel synthesis, phthalimide is first alkylated, and then hydrolyzed to produce primary amines. However, this method is not suitable for preparing aryl amines like aniline, because aryl halides (such as bromobenzene) do not readily undergo nucleophilic substitution reactions that are fundamental to this synthesis. Therefore, Statement II is also true.

Given these explanations, both statements are correct: Both Statement I and Statement II are true.