- Aalkylated product with ortho and para substitution.
- Bsecondary amine after acidic treatment.
- Can amide product.
- Dpositively charged nitrogen at benzene ring.
View written solutionFree
Correct answer: D
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Key fact about aniline in Friedel–Crafts reaction
Aniline is . In Friedel–Crafts alkylation, a Lewis acid catalyst such as is used.
The amino group of aniline has a lone pair on nitrogen. This lone pair strongly coordinates with :
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Effect of coordination/protonation on the ring
When nitrogen donates its lone pair, it acquires a positive character. The species behaves like an anilinium-type complex, and the benzene ring becomes strongly deactivated toward Friedel–Crafts alkylation.
This may be represented by resonance/complex forms in which nitrogen bears a positive charge:
Thus, instead of normal ortho/para alkylation, aniline forms a complex where the nitrogen is effectively positively charged and the ring is not activated for Friedel–Crafts reaction.
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Check each option
A: alkylated product with ortho and para substitution
Incorrect. Although is ordinarily an ortho/para-directing group, under Friedel–Crafts conditions it coordinates with and deactivates the ring.B: secondary amine after acidic treatment
Incorrect. Friedel–Crafts alkylation of aniline does not give a secondary amine after acidic treatment.C: an amide product
Incorrect. No amide is formed in Friedel–Crafts alkylation.D: positively charged nitrogen at benzene ring
Correct. Due to interaction of the amino group with the Lewis acid catalyst, nitrogen develops positive charge, preventing normal Friedel–Crafts alkylation. -
Final answer
Therefore, the correct option is:
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