Question

Consider the following statements: I. Aniline does not give Friedel-Crafts reaction. II. Aromatic primary amines cannot be prepared by Gabriel phthalimide synthesis.

• A. Both I and II
• B. Neither I nor II
• C. Only II
• D. Only I

Hint:

Aniline fails to undergo Friedel-Crafts reactions because it forms a complex with the Lewis acid catalyst. Gabriel synthesis is restricted mainly to aliphatic primary amines.

Answer 1

The Correct Option is A

Concept: This question is identical to Question 56 and tests important properties of aromatic amines.

Step 1: Aniline and Friedel-Crafts reaction. Aniline contains a lone pair on nitrogen. This lone pair forms a coordinate bond with Lewis acids such as \[ AlCl_3 \] used in Friedel-Crafts reactions. As a result, the catalyst becomes ineffective and the reaction does not proceed normally. Therefore Statement I is correct.

Step 2: Gabriel synthesis and aromatic amines. Gabriel synthesis proceeds through nucleophilic substitution of alkyl halides. Aryl halides do not undergo this reaction easily. Hence aromatic amines cannot be prepared using Gabriel phthalimide synthesis. Therefore Statement II is correct.

Step 3: Final conclusion. Both statements are correct. \[ \boxed{(A)\ \text{Both I and II}} \]