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Aniline does not undergo Friedel – Crafts reaction
  • a)
    Anilium ion deactivates any further reaction.
  • b)
    aluminium chloride, the catalyst reacts with NH2 group
  • c)
    nitrogen of aniline acquires positive charge
  • d)
    all of these
Correct answer is option 'D'. Can you explain this answer?
Verified Answer
Aniline does not undergo Friedel – Crafts reactiona)Anilium ion ...
NH2 has lp of electron which reacts with AlCl3 or other catalyst that we add to form anilium ion.
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Aniline does not undergo Friedel – Crafts reactiona)Anilium ion ...
Explanation:

Aniline does not undergo Friedel-Crafts reaction due to the following reasons:

1. Anilium ion deactivates any further reaction:

The lone pair of electrons on the nitrogen of aniline can donate electrons to the benzene ring, making it more electron-rich. This makes it difficult for another electrophile to attack the ring, which is necessary for the Friedel-Crafts reaction to occur. Additionally, the anilium ion that is formed during the reaction deactivates the ring towards further electrophilic attack, making the reaction even more difficult.

2. Aluminium chloride, the catalyst reacts with NH2 group:

Aniline is a weakly basic compound, and the lone pair of electrons on the nitrogen can interact with the aluminum chloride catalyst in the Friedel-Crafts reaction. This interaction can lead to the formation of a complex between the catalyst and the aniline molecule, which can hinder the reaction.

3. Nitrogen of aniline acquires positive charge:

During the Friedel-Crafts reaction, the nitrogen of aniline can acquire a positive charge due to the interaction with the electrophile. This positive charge can destabilize the molecule and make it more reactive towards further electrophilic attack. However, this positive charge can also lead to the formation of the anilium ion, which deactivates the ring towards further reaction.

Therefore, all of these reasons contribute to the inability of aniline to undergo the Friedel-Crafts reaction.
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