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Q7.14:
Give two reactions that show the acidic nature of phenol. Compare acidity of phenol with that of ethanol.

Solution :

1. Chemical Reactions Demonstrating the Acidic Nature of Phenol

Phenol ($C_6H_5OH$) exhibits acidic character due to the polar $O-H$ bond, where the electron-withdrawing phenyl group stabilizes the resulting phenoxide ion through resonance. The following two reactions provide empirical evidence for this acidity:

Reaction A: Reaction with Active Metals
Phenol reacts with reactive metals like sodium to liberate hydrogen gas, a characteristic property of Brønsted acids.

$2C_6H_5OH + 2Na \rightarrow 2C_6H_5ONa + H_2 \uparrow$
[Justification: Displacement reaction where $Na$ replaces the acidic hydrogen of the hydroxyl group.]

Reaction B: Reaction with Strong Bases
Phenol undergoes neutralization when treated with aqueous sodium hydroxide to form sodium phenoxide and water.

$C_6H_5OH + NaOH \rightarrow C_6H_5ONa + H_2O$
[Justification: Neutralization reaction between an acid (phenol) and a base (NaOH) to form a salt and water.]

2. Comparative Analysis: Phenol vs. Ethanol

The relative acidity of phenol and ethanol is determined by the stability of their respective conjugate bases: the phenoxide ion ($C_6H_5O^-$) and the ethoxide ion ($C_2H_5O^-$).

Feature Phenol ($C_6H_5OH$) Ethanol ($C_2H_5OH$)
Conjugate Base Phenoxide ion ($C_6H_5O^-$) Ethoxide ion ($C_2H_5O^-$)
Electronic Effect Resonance stabilization Inductive effect ($+I$ effect)
Stability High (negative charge delocalized into ring) Low (alkyl group intensifies negative charge)
Acidity More acidic Less acidic

Analytical Justification:

  • Phenol: The lone pair of electrons on the oxygen atom in the phenoxide ion enters into resonance with the $\pi$-system of the benzene ring. This delocalization spreads the negative charge across the ortho and para positions, significantly stabilizing the anion [Per the Resonance Theory].
  • Ethanol: The ethyl group ($C_2H_5-$) is an electron-donating group ($+I$ effect). It increases the electron density on the oxygen atom, thereby destabilizing the ethoxide ion [Per the Inductive Effect Principle].

3. Visual Representation of Phenoxide Resonance

O⁻ Resonance Stabilization CH₃-CH₂-O⁻ Inductive Destabilization

Final Solution: Phenol is significantly more acidic than ethanol because the negative charge on the phenoxide ion is delocalized via resonance throughout the benzene ring, whereas the negative charge on the ethoxide ion is intensified by the electron-releasing inductive effect of the ethyl group.


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