Chemistry Alcohols & Phenols SET 2019
PMDC Verified Question 64 of 95
Ethanol, ethanoic acid and phenol all contain acidic functional groups, the order of the acidic strength is Ethanoic acid > Phenol > Ethanol. This is mainly due to
A
Electron releasing (donating) effect of ethanoic acid is greater than that of ethanol
B
Electron releasing (donating) effect of phenol is greater than that of ethanol
C
Electron with drawing effect of phenol is greater than that of ethanol
D
Electron with drawing effect of ethanoic acid is greater than that of phenol
Tap any option to test your recall and reveal the step-by-step Propolis autopsy.

Propolis Cognitive Error Autopsy

Official Correct Choice:
Option D: Electron with drawing effect of ethanoic acid is greater than that of phenol
Concept:

Acidic strength is determined by the electron-withdrawing capacity of the group attached to the acidic -OH, which stabilizes the resulting negative charge on the conjugate base.

Formula:

$$ K_a \propto \text{Stability of anion} \propto \text{Electron withdrawing groups} $$

Solution:

  • In ethanoic acid, the carbonyl group (C=O) exerts a strong electron-withdrawing inductive and resonance effect, massively stabilizing the acetate ion.


  • In phenol, the phenyl ring also withdraws electrons via resonance, stabilizing phenoxide, but it is less effective than the carbonyl group.


  • Ethanol has an electron-donating alkyl group, destabilizing the ethoxide ion.


  • Thus, the electron-withdrawing effect of ethanoic acid is greater than that of phenol.


Why other options are incorrect:

Acidity is not increased by electron-releasing effects (rules out A and B). While C is partially true (phenol withdraws more than ethanol), D is the primary reason that bridges the complete trend provided in the question.

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