Chemistry Hydrocarbons MDCAT 2018
PMDC Verified Question 42 of 65
Which one of the following acts as an electrophile in the electrophilic substitution of benzene with bromine?
A
\( \text{Br}^+ \)
B
\( \text{FeCl}_4^- \)
C
\( \text{Fe}^{+3} \)
D
\( \text{Fe}^{+2} \)
Tap any option to test your recall and reveal the step-by-step Propolis autopsy.

Propolis Cognitive Error Autopsy

Official Correct Choice:
Option A: \( \text{Br}^+ \)
Concept:

Electrophilic aromatic substitution demands a powerful electrophile, normally generated via the interaction of the reagent with a Lewis acid catalyst.

Formula:

$$ \text{Br}_2 + \text{FeBr}_3 \rightarrow \text{Br}^+ + \text{FeBr}_4^- $$

Solution:

  • When bromine (\( \text{Br}_2 \)) interacts with a Lewis acid (like \( \text{FeBr}_3 \) or \( \text{FeCl}_3 \)), the halogen bond is polarized and broken.


  • This heterolytic cleavage produces the highly reactive bromonium ion, \( \text{Br}^+ \), which is electron-deficient.


  • \( \text{Br}^+ \) is the actual electrophile that attacks the electron-rich pi cloud of the benzene ring.


Why other options are incorrect:

  • \( \text{FeCl}_4^- \) is a negatively charged counterion (a weak nucleophile), not an electrophile.


  • \( \text{Fe}^{+3} \) and \( \text{Fe}^{+2} \) represent oxidation states of iron in the catalyst; they do not act as the carbon-attacking electrophile in the aromatic substitution step.

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