Which of the following amines can be prepared by Gabriel phthalimide reaction?

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JEE Mains Previous Paper 1 (Held On: 08 Apr 2019 Shift 1)
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  1. n-butylamine
  2. triethylamine
  3. t-butylamine
  4. neo-pentylamine

Answer (Detailed Solution Below)

Option 1 : n-butylamine
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JEE Main 04 April 2024 Shift 1
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Detailed Solution

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Concept:

Gabriel phthalimide synthesis is used for the preparation of primary amines, phthalimide on treatment with ethanolic potassium hydroxide formed salts of phthalimide which in heating with alkyl halide followed by alkyl hydrolysis produce corresponding primary amines. Aromatic primary amines cannot be prepared by this synthesis because aryl halides do not undergo nucleophilic substitution with the anion formed by phthalimide.

The Gabriel phthalimide reaction transforms primary alkyl halides into primary amines.

From the given options, n-butylamine is the only aliphatic primary amine compound.

Actually, Gabriel phthalimide synthesis is used for the preparation of aliphatic primary amines. It involves nucleophilic su nucleophilic bstitution (SN2) of alkyl halides by the anion formed by the phthalimide. Hence, aromatic primary amines cannot be prepared by this process.
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