Q.Which of the following species does not exert a resonance effect?
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Start your 14-day free trial to unlock the full solution →The anilinium ion, C6H5NH3+, does not show the substituent resonance effect because its nitrogen has no lone pair left to donate.
In aniline (C6H5NH2), the lone pair on nitrogen conjugates with the benzene ring's π system, giving resonance structures that place negative charge at the ortho/para carbons — this is why aniline is more reactive than benzene towards electrophilic substitution and less basic than typical aliphatic amines.
In the anilinium ion (C6H5NH3+), the nitrogen has already used its lone pair to bond the extra proton (forming the fourth N-H bond), so there is no lone pair left on nitrogen to conjugate with the ring. Hence this species does not exert the (lone-pair) resonance effect the way aniline, phenol, and chlorobenzene do.
By contrast: …
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