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.
Both Statement I and Statement II are incorrect.
Statement I is correct and Statement II is incorrect.
Statement I is incorrect and Statement II is correct.
Both Statement I and Statement II are correct.
Statement I is correct: Aniline does not undergo Friedel-Crafts alkylation or acylation reactions. This is because aniline is a basic compound (Lewis base) and reacts with the Lewis acid catalyst (such as anhydrous ) to form a complex/salt. As a result, the nitrogen atom acquires a positive charge, acting as a strong deactivating group, thus preventing electrophilic substitution from occurring.
Statement II is also correct: Gabriel phthalimide synthesis is exclusively used for the preparation of pure aliphatic primary amines. It cannot be used to prepare aromatic primary amines like aniline because the required substrate, aryl halides, do not undergo nucleophilic substitution () with the phthalimide anion under normal conditions.
This question aligns with the NEET CHEMISTRY syllabus, specifically targeting concepts from Amines. Mastering this topic is crucial for scoring well in the upcoming medical entrance examinations. Solving conceptually related problems will help you understand the nuances of these concepts and improve your problem-solving speed.
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