Answer:
(i) Aniline does not undergo Friedel-Crafts reaction (alkylation
and acetylation) as it forms salt with AICI3 (catalyst, Lewis acid) ? group (electron-pair
donor, Lewis base) acquires positive charge and thus - group in
aniline becomes deactivating group for further reaction.
[1]
(ii)
In the above method, when R?X reacts with NH3 1°,
2°, 3° amines and quaternary ammonium salt is formed. In Gabriel phthalimide
reaction, two H of NH3 are blocked by phthalimide formation (only one H is left
reactive), hence 1° amine is formed.
[1]
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