12th Class Chemistry Amines

  • question_answer 21)
    Why cannot aromatic primary amines be prepared by Gabriel phthalimide synthesis? Gabriel phthalimide synthesis involves breaking of  where, X is halogen) bond and in aromatic halides bond acquires double bond character.  

    Answer:

    In Gabriel phthalimide reaction, potassium salt of phthalimide is formed. It reacts readily with alkyl halide to form the corresponding alkyl derivative. But aryl halide does not react with potassium phthalimide. BecauseC?X bond in haloarene (alkyl halide) is difficult to be cleaved due topartial double bond character. So, aromatic primary amines cannot beprepared by Gabriel phthalimide synthesis.      


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