Question:

Given below are two statements, one is labelled as Assertion A and the other is labelled as Reason R

Assertion (A) : Gabriel phthalimide reaction can be used to prepare aryl and alkyl amines. 

Reason (R) : Aryl halides have same reactivity as alkyl halides towards nucleophilic substitution reactions

In the light of the above statements, choose the correct answer from the options given below

Updated On: Apr 6, 2023
  • If both Assertion and Reason are true and Reason is correct explanation of Assertion.
  • If both Assertion and Reason are true but Reason is not the correct explanation of Assertion.
  • If Assertion is true but Reason is false.
  • If both Assertion and Reason are false.
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The Correct Option is D

Solution and Explanation

Gabriel phthalimide reaction can be used to prepare alkyl and alkyl primary amines. These undergo nucleophilic substitution reactions but aryl halides do not.
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Concepts Used:

Preparation of Amines

  • Reduction of nitro compounds: Nitro compounds are reduced to amines by reduction with metals in an acidic medium or by passing them through hydrogen gas in the presence of finely divided nickel, palladium, or platinum.
  • Ammonolysis of alkyl halides: Alkyl benzyl halide undergoes a nucleophilic substitution reaction while reacting with an ethanolic solution of ammonia where the halogen atom is replaced by an amino group and this process of splitting of the C-X bond by an ammonia molecule is called ammonolysis.
  • Reduction of Nitriles: On reduction of nitriles with lithium or aluminum hydride or catalytic hydrogenation are used.
  • Reduction of amides: On reduction, the amides with lithium aluminum hydride yield amines.
  • Gabriel phthalimide synthesis: Gabriel synthesis is used to prepare primary amines. Phthalimidewhen treated with ethanolic potassium hydroxide, forms potassium salt of phthalimide which when heated with alkyl halide followed by alkaline hydrolysis leads to the formation of the corresponding primary amine.
  • Hoffmann bromamide degradation reaction: In the Hoffmann bromamide degradation reaction, the transfer of an alkyl or aryl group takes place from the carbonyl carbon of the amide to the nitrogen atom. The amine so formed, therefore, contains one carbon less than that present in the initial amine.