Question

Which of the following does not show a resonance effect

• A. $C_6H_5OH$
• B. $C_6H_5Cl$
• C. $C_6H_5NH_2$
• D. $C_6H_5NH_3$

Answer 1

Answer: (D)

$C_6H_5NH_3$

Answer 2

$C_6H_5\overset{+}{N}H_3$ (protonated aniline) does not show resonance effect. The nitrogen of protonated aniline does not have any non-bonding electrons that can be delocalised. Whereas all other options have non-bonding electrons that can be delocalised.

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