Chemistry, asked by Arav75788, 1 year ago

Here is an organic question for you


Prepare n- butylamine by Gabriel synthesis.

Give the whole reaction and mechanism.


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Answered by biologyking1977
3

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Answered by Anonymous
11

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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.

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