Chemistry Hydrocarbons PMC 2021
PMDC Verified Question 19 of 65
Which of the following act as electrophile during nitration of benzene?
A
\( \text{NO}^+ \)
B
\( \text{NO}_3^+ \)
C
\( \text{HNO}_2^+ \)
D
\( \text{NO}_2^+ \)
Tap any option to test your recall and reveal the step-by-step Propolis autopsy.

Propolis Cognitive Error Autopsy

Official Correct Choice:
Option D: \( \text{NO}_2^+ \)
Concept:

Nitration relies on the creation of a highly electrophilic, positively charged nitrogen species from nitric acid.

Formula:

$$ \text{HNO}_3 + 2\text{H}_2\text{SO}_4 \rightleftharpoons \text{NO}_2^+ + \text{H}_3\text{O}^+ + 2\text{HSO}_4^- $$

Solution:

  • Concentrated sulfuric acid protonates nitric acid, forcing it to lose a water molecule.


  • The resulting species is the nitronium ion, \( \text{NO}_2^+ \).


  • This linear ion contains a central nitrogen with a full positive charge and empty orbitals, making it the aggressive electrophile that attacks the benzene pi cloud.


Why other options are incorrect:

  • \( \text{NO}^+ \) is the nitrosonium ion, used in nitrosation, not nitration.


  • \( \text{NO}_3^+ \) and \( \text{HNO}_2^+ \) are not the stable active intermediates generated in standard nitrating mixtures.

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