- AReimer Tiemann reaction
- BFriedel Craft's alkylation
- CAcetylation of aniline
- DFriedel Craft's acylation
View written solutionFree
Correct answer: B
- Understand the question
We need to identify the reaction in which polysubstitution is a major drawback.
Polysubstitution means that after one substituent enters the aromatic ring, the product becomes even more reactive and undergoes further substitution, giving di-/tri-substituted products.
- Check each option
A. Reimer–Tiemann reaction
This reaction is used for formylation of phenols, typically giving salicylaldehyde.
- It is not especially known for polysubstitution as the major drawback.
- Main issue is usually mixture of ortho/para products or moderate yield.
So, A is not correct.
B. Friedel–Crafts alkylation
In Friedel–Crafts alkylation, an alkyl group is introduced into an aromatic ring using an alkyl halide and a Lewis acid such as .
Example:
Now, an alkyl group is electron-donating due to the effect and hyperconjugation. Therefore, once the first alkyl group enters the ring, the ring becomes more reactive than benzene itself.
So the product alkylbenzene undergoes further alkylation easily:
Hence, polysubstitution is a major drawback of Friedel–Crafts alkylation.
So, B is correct.
C. Acetylation of aniline
Acetylation of aniline forms acetanilide:
This is protection of the amino group, not an aromatic substitution reaction where polysubstitution is the main issue.
So, C is not correct.
D. Friedel–Crafts acylation
In Friedel–Crafts acylation, an acyl group is introduced:
The acyl group is electron-withdrawing due to the and effects, so after one acyl group enters, the ring becomes less reactive.
Therefore, polysubstitution does not occur easily in Friedel–Crafts acylation.
So, D is not correct.
- Conclusion
The reaction in which polysubstitution is a major drawback is:
- Comparison with stored correct answer
Stored correct answer: B
Our derived answer: B
They match.
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