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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:
Aniline complexes with AlCl3 catalyst (killing Friedel-Crafts) AND aryl halides cannot do SN2 with phthalimide (killing Gabriel synthesis) -> Both are TRUE!
Friedel-Crafts alkylation requires an anhydrous Lewis acid catalyst like AlCl3 to generate carbocation electrophiles. Aniline has a basic lone pair on nitrogen that donates to the electron-deficient AlCl3, forming a coordinate adduct. The resulting positive formal charge on nitrogen (-NH2⁺-AlCl3⁻) exerts a potent electron-withdrawing (-I) effect, severely deactivating the benzene ring against electrophilic aromatic substitution:
Gabriel phthalimide synthesis is exclusively designed for the preparation of primary aliphatic amines. In the key step, potassium phthalimide acts as a nucleophile in an SN2 displacement of halide from an alkyl halide. Because aryl halides (like bromobenzene) have partial double bond character due to resonance and the aryl ring repels backside nucleophilic attack, they do not undergo SN2 reactions:
Diagnose every choice: Know exactly why the right option works and why distractors fail.
Statement II is completely true: aromatic 1° amines cannot be prepared by Gabriel synthesis.
Statement I is completely true: aniline fails Friedel-Crafts reactions.
Both canonical limitations of aniline reactions are 100% verified by NCERT.
Both statements are well-known fundamental principles of amine chemistry.
Gabriel phthalimide synthesis produces ONLY primary aliphatic amines (R-NH2). It completely fails for aromatic primary amines (Ar-NH2) because aryl halides cannot undergo SN2 substitution.
"Aniline does not undergo Friedel-Crafts reaction due to salt formation with AlCl3; aromatic primary amines cannot be prepared by Gabriel synthesis because aryl halides do not undergo SN2."
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