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Prepare n- butylamine by Gabriel synthesis.
Give the whole reaction and mechanism.
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GABRIEL PHTHALIMIDE SYNTHESIS :-
=> when a phthalimide is treated with ethanolic potassium hydroxide ( KOH ), it forms salt of phthalimide which on heating with alkyl halide follwed by alkaline hydrolysis forms corresponding primary amines.
=> Aromatic primary amines cannot be prepared by this method.
This is because aryl halides do not undergo nucleophilic substitution with the anion formed by phthalimide.
Now,
Preparation of n- butylamine by Gabriel synthesis :-
Step 1.
potassium phthalimide is treated with ethanolic KOH it forms potassium salt of phthalimide called POTASSIUM PHTHALIMIDE.
Step 2.
This potassium salt is now treated with n- bromobutane which takes out the potassium bromide salt forming N- butylphthalimide.
Step 3.
Now, the N- butylphthalimide is treated with water to undergo hydrolysis forming the phthalic acid and 1° amine.
Result:
The 1° amine obtained is n- butylamine.
Note:-
The whole reaction and its mechanism is in the attachment.