Question:

Which of the following does not show a resonance effect

Updated On: May 24, 2024
  • $C_6H_5OH$
  • $C_6H_5Cl$
  • $C_6H_5NH_2$
  • $C_6H_5NH_3$
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The Correct Option is D

Solution and Explanation

$C_6H_5\overset{+}{N}H_3$ (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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Concepts Used:

Structure of Amines

The structure of Amines is shown below:

Alkyl Amines:

Alkylamines consist of tetrahedral nitrogen centers where the C-N-H and C-N-C bond angle is 109°. The distance between C-N bonds is smaller in comparison to the C-C range. The amines can also display a chiral property wherein the center of the nitrogen atom holds for replacements which creates solo pairs.

The bond angle in the case of trimethylamine is 108° which results in the Pyramidal structure of trimethylamine-

Aromatic Amine:

Due to the mixture of the solo pair with the aryl substituent, nitrogen nearly has a planar structure in aromatic amines. The C-N range is very short. In aniline, the distance between C-N bonds is similar to the distance between C-C bonds.

Read More: Structure of Amines