Chemistry Hydrocarbons NUMS 2024
PMDC Verified Question 16 of 65
The most readily sulphonated compound is:
A
Benzene
B
Chlorobenzene
C
Nitrobenzene
D
Toluene
Tap any option to test your recall and reveal the step-by-step Propolis autopsy.

Propolis Cognitive Error Autopsy

Official Correct Choice:
Option D: Toluene
Concept:

The rate of electrophilic aromatic substitution (like sulfonation) depends on the electron density of the aromatic ring. Electron-donating groups activate the ring (making it react faster), while electron-withdrawing groups deactivate it.

Solution:

  • Benzene: The baseline standard.


  • Nitrobenzene: The \( -\text{NO}_2 \) group is highly electronegative and strongly withdraws electrons via resonance, heavily deactivating the ring.


  • Chlorobenzene: Halogens withdraw electrons inductively, making the ring mildly deactivated compared to benzene.


  • Toluene (Methylbenzene): The methyl group (\( -\text{CH}_3 \)) pushes electron density into the ring through inductive effects and hyperconjugation. This makes the ring significantly more electron-rich and thus most reactive/readily sulphonated among the choices.


Why other options are incorrect:

  • Benzene lacks the activating methyl group.


  • Chlorobenzene and Nitrobenzene are deactivated and react much slower than pure benzene.

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