Practicing Success

Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Amines

Question:

Assertion: Gabriel phthalimide reaction can be used to prepare both aryl and aralkyl amines.

Reason: Aryl halides are as reactive as aralkyl halides towards nucleophilic substitution reactions. 

Options:

Both Assertion and Reason are correct and the Reason is the correct explanation for the Assertion.

Both Assertion and Reason are correct and the Reason is not the correct explanation for the Assertion.

Assertion is correct but the Reason is incorrect.

Both Assertion and Reason are incorrect.

Correct Answer:

Both Assertion and Reason are incorrect.

Explanation:

The correct answer is option 4. Both Assertion and Reason are incorrect.

Assertion: Gabriel phthalimide reaction can be used to prepare both aryl and aralkyl amines.

The Gabriel phthalimide reaction, also known as the Gabriel synthesis, is a method used to prepare primary amines from alkyl halides. In this reaction, a phthalimide ion reacts with an alkyl halide to form an N-alkylphthalimide intermediate. Subsequent hydrolysis of this intermediate results in the formation of a primary amine.

However, aryl halides typically do not react efficiently in the Gabriel synthesis. This is because aryl halides are less reactive towards nucleophilic substitution reactions compared to alkyl halides. The electron-withdrawing nature of the aromatic ring in aryl halides makes them less susceptible to nucleophilic attack. As a result, the Gabriel synthesis is not commonly used for preparing aryl amines.

Reason: Aryl halides are as reactive as aralkyl halides towards nucleophilic substitution reactions.

This statement is incorrect. Aryl halides are generally less reactive than aralkyl halides towards nucleophilic substitution reactions. The difference in reactivity arises from the electronic and steric effects of the aryl group.

Aryl halides undergo nucleophilic substitution reactions less readily due to the resonance stabilization of the aryl group. The delocalization of π electrons in the aromatic ring results in a partial positive charge on the carbon atom bearing the halogen, making it less electrophilic. As a result, aryl halides exhibit lower reactivity towards nucleophiles compared to alkyl halides.

In contrast, aralkyl halides (aryl-alkyl compounds) may exhibit higher reactivity than aryl halides due to the presence of an alkyl group, which can provide additional electrophilicity and may enhance the rate of nucleophilic substitution reactions.

Therefore, both the Assertion and the Reason are incorrect:

The Gabriel phthalimide reaction is primarily used for alkyl halides, not aryl halides.  Aryl halides are generally less reactive than aralkyl halides towards nucleophilic substitution reactions due to resonance stabilization effects.