Question

Gabriel phthalamide synthesis​

Answer 1

The Gabriel synthesis is a chemical reaction that transforms primary alkyl halides into primary amines. Traditionally, the reaction uses potassium phthalimide. The reaction is named after the German chemist Siegmund Gabriel.

The reaction of phthalimide with ethanolic KOH gives potassium salt of phthalimide. It is then heated with alkyl halide to form N-alkyl phthalimide. Aromatic primary amines cannot be prepared as aryl halides do not undergo nucleophilic substitution with anion formed by phthalimide

The Gabriel method generally doesn't work with secondary alkyl halides. Another disadvantage of this synthesis is that using acidic/basic hydrolysis gives a low yield whereas the usage of hydrazine can make the conditions of the synthesis relatively harsh.

Answer 2

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