Question

The method by which aniline cannot be prepared is

• A. Nitration of benzene followed by reduction with Sn and con HCI
• B. Degradation of benzamide with bromine in alkaline solution
• C. Reduction of nitrobenzene with $H_2 / Pd$ is ethanol
• D. Potassium salt of phthalimide treated with chlorgbenzene followed by the hydrolysis with aqueous NaOH solution

Answer 1

The Correct Option is D

Aniline is an aromatic amine, and there are several synthetic routes to prepare it. Let's evaluate each given option to determine which method cannot be used to synthesize aniline:

1. Nitration of benzene followed by reduction with Sn and conc. HCl:
   • Benzene can be converted to nitrobenzene via nitration.
   • Nitrobenzene can then be reduced to aniline using a reducing agent like Sn and conc. HCl.
   • This method is a well-known process for synthesizing aniline.
   • Hence, this method can indeed prepare aniline.
2. Degradation of benzamide with bromine in alkaline solution (Hoffmann bromamide reaction):
   • In this reaction, benzamide is degraded to aniline after treatment with bromine in the presence of an alkali.
   • The reaction involves migration of the aryl group to nitrogen with a loss of carbon dioxide.
   • This is a known method for aniline synthesis.
3. Reduction of nitrobenzene with H_2 / Pd in ethanol:
   • Nitrobenzene can be reduced using hydrogen gas and a palladium catalyst.
   • This reduction yields aniline as the product.
   • Therefore, this method is also viable for preparing aniline.
4. Potassium salt of phthalimide treated with chlorobenzene followed by hydrolysis with aqueous NaOH solution (Gabriel phthalimide synthesis):
   • The Gabriel phthalimide synthesis is typically used for the preparation of primary aliphatic amines, not aromatic amines.
   • In this process, the phthalimide anion acts as a nucleophile and reacts with alkyl halides. Subsequent hydrolysis leads to the liberation of the amine.
   • However, this method is ineffective for forming aromatic amines like aniline because the aryl halide (chlorobenzene) does not react favorably under these conditions.
   • Thus, this method cannot be used to prepare aniline.

In conclusion, the method by which aniline cannot be prepared is: Potassium salt of phthalimide treated with chlorobenzene followed by hydrolysis with aqueous NaOH solution.