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Question 32 of 34

Q.Which of the following species does not exert a resonance effect ?

(a) C6H5NH2
(b) C6H5OH
(c) C6H5NH3+
(d) C6H5Cl
Puducherry TnboardTamil Nadu HSC First Year (DGE) Board 2025MCQ· 1mImportance★★★★★
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C6H5NH3+ (the anilinium/phenylammonium ion) shows no resonance effect because nitrogen's lone pair, which would otherwise conjugate with the ring, is used up forming a bond to the extra proton.

Check each species for a lone pair (or pi electrons) available to conjugate with the benzene ring's pi system:

  1. C6H5NH2 (aniline): nitrogen has a lone pair that conjugates into the ring, donating electron density by resonance (+M effect) — this is why aniline is a stronger base... actually more relevantly here, why the ring is activated towards electrophilic substitution. Resonance effect present.
  2. C6H5OH (phenol): oxygen's lone pair conjugates into the ring similarly (+M effect), activating the ring. Resonance effect present. …

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