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Explain why aromatic primary amines can'...

Explain why aromatic primary amines can't be prepared by Gabriel phthalimide process.

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The main step in the Gabriel phthalimide synthesis is a `S_(N)2` reaction in which the nucleophile, phthalimide anion displaces the halide ion from alkyl halides to form N-alkyl phthalimide which by subsequent acid or alkaline hydrolysis gives the corresponding aliphatic primary amine.
However, in aryl halides, nucleophilic substitution reaction does not occur easily due to the resonance in Ar-X. That is why, aromatic primary amines cannot be prepared by Gabriel phthalimide reaction.
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Knowledge Check

  • The basic character of amine can be explained :

    A
    In terms of lewis and Arrhenius concept
    B
    Only in terms of Lowry Bronsted concept
    C
    In terms of Lewis and Lowry Bronsted concept
    D
    Only in Lewis concept

  • Ethly amine can be prepared by the action of Br_2 and NaOH on :

    A
    Acetamide
    B
    Propionamide
    C
    Methylamine
    D
    Methyl cyanide

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