Chemistry Alcohols & Phenols BUMHS 2022
PMDC Verified Question 52 of 95
Phenol is more reactive than benzene towards electrophilic substitution. This characteristic is due to which of the following?
A
Hydrogen bonding
B
Inductive effect
C
Strong mesomeric effect
D
Weak mesomeric effect
Tap any option to test your recall and reveal the step-by-step Propolis autopsy.

Propolis Cognitive Error Autopsy

Official Correct Choice:
Option C: Strong mesomeric effect
Concept:

The reactivity of an aromatic ring towards electrophiles is governed by the electron density of the ring. Groups that donate electrons into the ring activate it.

Formula:

Not applicable to this conceptual question.

Solution:

  • The oxygen atom of the -OH group has lone pairs of electrons.


  • Despite oxygen being more electronegative than carbon (which exerts an electron-withdrawing inductive effect, -I), the lone pairs heavily overlap with the \(\pi\)-system of the ring.


  • This donates massive electron density via resonance, known as a strong positive mesomeric effect (+M).


  • This +M effect vastly outweighs the -I effect, making the ring highly reactive.


Why other options are incorrect:

Hydrogen bonding affects physical properties (boiling point, solubility) but not the internal ring electron density. The inductive effect of -OH is actually electron-withdrawing (-I), which would deactivate the ring if not for the overpowering mesomeric effect.

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