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NEET CHEMISTRYMedium

Mark the reaction that does not yield aniline from the given options:

A

Hydrolysis of phenyl isocyanide with an acidic solution

B

Degradation of benzamide with bromine in alkaline solution

C

Reduction of nitrobenzene with H2/PdH_2/Pd in ethanol

D

Treatment of potassium salt of phthalimide with chlorobenzene followed by hydrolysis in an aqueous NaOH solution

Step-by-Step Solution

Gabriel phthalimide synthesis is used for the preparation of primary aliphatic amines. It cannot be used for the preparation of primary aromatic amines (like aniline) because aryl halides (such as chlorobenzene) do not undergo nucleophilic substitution with the anion formed by phthalimide due to the resonance stabilization and partial double bond character of the C-Cl bond.

Other reactions:

  1. Hydrolysis of phenyl isocyanide with an acidic solution yields aniline and formic acid.
  2. Hofmann bromamide degradation of benzamide with bromine in an alkaline solution yields aniline.
  3. Catalytic reduction of nitrobenzene with H2/PdH_2/Pd in ethanol yields aniline.
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