Question:

Amine that cannot be prepared by Gabriel- phthalimide synthesis is

Updated On: Jun 9, 2024
  • aniline
  • benzyl amine
  • methyl amine
  • iso-butyl amine
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The Correct Option is A

Solution and Explanation

Only aliphatic primary amines can be prepared by Gabriel synthesis. Aniline cannot be prepared by this method because aryl halides ( $ {{C}_{6}}{{H}_{5}}Cl $ or $ {{C}_{6}}{{H}_{5}}Br $ ) do not undergo nucleophilic substitution with potassium phthalimide under ordinary conditions to give N-phenyl phthalimide (ie, cleavage of $ CX $ bond in haloarenes is quite difficult)
( $ RX= $ aliphatic halide)
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Concepts Used:

Amines

Amine is a type of compound which is derived from ammonia (NH3). According to Organic chemistry, they are basically classified as the functional groups of the organic nitrogen compounds that contain nitrogen atoms with a lone pair.

Amine - Types

Primary Amines:

It is formed when one hydrogen atom in ammonia is substituted by an alkyl or aromatic group. Amino acids and methyl amine are the best examples that why aromatic amines include aniline.

Secondary Amines:

Amines that have two organic substitutes either alkyl or aryl ones or both and are bound to the nitrogen together with one hydrogen are termed as secondary amines. For Example, Dimethylamine.

Tertiary Amines:

Tertiary Amines are the amines where the nitrogen consists of three organic substitutes. For example, Trimethylamine and EDTA.