Gabriel Synthesis Reaction Mechanism - Alkyl Halide to Primary Amine

This organic chemistry video tutorial provides 2 versions of the mechanism of the gabriel synthesis reaction which converts alkyl halides into primary amines.  It uses phthalamide as the starting material which has an imide functional group.  A strong base such as KOH is used to activate the imide by deprotonation followed by an SN2 backside attack of the nitrogen on the alkyl halide.  If Hydrazine is used in the third step, the side product will be Phthalimide Hydrazide.  If acid hydrolysis H2O / HCl is used in the third, Phthalic acid will be produced instead.

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• #amine
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• #hydrazine
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