Chemistry Hydrocarbons MDCAT 2017
PMDC Verified Question 45 of 65
When benzene reacts with Acetyl chloride (\( \text{CH}_3\text{COCl} \)) in the presence of \( \text{AlCl}_3 \) acetophenone is formed. The electrophile in this reaction will be
A
\( \text{CH}_3\text{C}^+\text{O} \)
B
\( \text{C}^+\text{H}_3 \)
C
\( \text{AlCl}_3 \)
D
\( \text{CH}_3\text{COCl} \)
Tap any option to test your recall and reveal the step-by-step Propolis autopsy.

Propolis Cognitive Error Autopsy

Official Correct Choice:
Option A: \( \text{CH}_3\text{C}^+\text{O} \)
Concept:

In Friedel-Crafts acylation, the Lewis acid catalyst serves specifically to strip a chloride ion from the acyl chloride, producing the active electrophile.

Formula:

$$ \text{CH}_3\text{COCl} + \text{AlCl}_3 \rightarrow \text{CH}_3\text{C}^+=\text{O} + \text{AlCl}_4^- $$

Solution:

  • Acetyl chloride (\( \text{CH}_3\text{COCl} \)) loses \( \text{Cl}^- \) to \( \text{AlCl}_3 \).


  • This generates the highly reactive, resonance-stabilized acylium ion: \( \text{CH}_3\text{C}^+\text{O} \).


  • This acylium ion acts as the direct electrophile that attacks the benzene ring to yield acetophenone.


Why other options are incorrect:

  • \( \text{C}^+\text{H}_3 \) is a methyl carbocation, which would be the electrophile for Friedel-Crafts alkylation using methyl chloride, not acylation.


  • \( \text{AlCl}_3 \) is the catalyst, not the attacking electrophile on the ring.


  • \( \text{CH}_3\text{COCl} \) is the neutral starting reagent, not yet activated into an electrophile.

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