
- A– group is highly meta-directive
- B– substitution always takes place at meta-position
- CFormation of anilinium ion
- Dlow temperature
View written solutionFree
Correct answer: C
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Identify the reaction situation
The question refers to nitration of aniline (or a related ring containing the group), where along with the expected products, a meta-nitro product is also formed.
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Usual directing effect of
The amino group is normally a strong activating, ortho/para-directing group because its lone pair donates electron density into the benzene ring by resonance.
So, if free aniline undergoes electrophilic substitution, we expect mainly:
- ortho product
- para product
Therefore, option A is false because is not meta-directing.
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What happens during nitration conditions?
Nitration is carried out in a strongly acidic medium, usually with a mixture of concentrated and concentrated .
In this acidic medium, the amino group gets protonated:
This species is called the anilinium ion.
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Directing effect of anilinium ion
The group is electron-withdrawing and meta-directing.
Hence, once aniline is converted into anilinium ion under nitration conditions, some substitution occurs at the meta position, which explains the formation of the meta-nitro product.
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Check other options
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B: " substitution always takes place at meta-position"
False. The entering electrophile is the nitronium ion , and the position of substitution depends on the group already present on the ring. -
D: low temperature
False. Low temperature is not the reason for meta substitution here.
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Conclusion
The meta product is formed because the amino group is protonated in acidic medium to give anilinium ion, which is meta-directing.
Therefore, the correct option is:
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