Chemistry Alcohols & Phenols MDCAT 2017
PMDC Verified Question 79 of 95
The phenoxide ion is more stable than ethoxide ion as
A
Lone pair on O-atom overlaps with the delocalized \(\pi\)-bonding system in benzene
B
Oxygen atom is directly bonded with benzene ring in phenoxide ion
C
The negative charge is localized on oxygen atom of phenoxide ion
D
The negative charge is delocalized on oxygen atom of ethoxide ion
Tap any option to test your recall and reveal the step-by-step Propolis autopsy.

Propolis Cognitive Error Autopsy

Official Correct Choice:
Option A: Lone pair on O-atom overlaps with the delocalized \(\pi\)-bonding system in benzene
Concept:

The stability of a conjugate base determines the acidity of the parent compound. Resonance delocalization significantly enhances stability.

Formula:

Not applicable to this conceptual question.

Solution:

  • In the phenoxide ion (\(\text{C}_6\text{H}_5\text{O}^-\)), the negative charge resides on the oxygen atom.


  • One of the lone pairs on the oxygen atom resides in a p-orbital that is perfectly parallel to the \(\pi\)-system of the aromatic ring, allowing the negative charge to be delocalized over the ortho and para carbon atoms of the ring.


  • This dispersion of charge heavily stabilizes the phenoxide ion relative to the ethoxide ion, where the charge is completely localized on the oxygen.


Why other options are incorrect:

Option C is factually wrong (the charge is delocalized, not localized). Option D is wrong because ethoxide has no \(\pi\)-system for delocalization. Option B is a structural fact but doesn't explain the mechanism of stability like resonance (Option A) does.

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