Gabriel phthalimide synthesis is a very convenient method for the preparation of pure aliphatic amines ( especially primary amines) Phthalimide on treatment with ethanolic KOH gives potassium phthalimide which on heating with a suitable alkyl hallide gives N-substituted phthalimides. These upon susbsequent hydrolysis with dil.HCl under pressure or with alkali gives primary amines.
Step 1: Phthalimide is treated with KOH to form potassium phthalimide
Step 2: Potassium phthalimde is treated with suitable alkyl hallide to form N-substituted phthalimides.
Step 3: N-substituted phthalimides undergoes hydrolysis in the prsence of dil HCl or with alkali(NaOH) to give primary amines.
∴ Gabriel phthalimide synthesis results in the formation of primary(1° amine) only. Secondary or tertiary amines are not formed through this synthesis. Hence, Gabriel phthalimide synthesis preferred for the formation of primary amines only.
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