Phenols are more acidic than alcohols due to the resonance stabilization of the phenoxide anion by the aromatic ring, which increases its stability and propensity to dissociate. Most phenols are not soluble in aqueous sodium bicarbonate, unlike carboxylic acids, allowing for their separation. A video link is provided for further information.

1. Acidity of phenols

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Phenols are more acidic than alcohols because the phenoxide anion is resonance-stabilized by the
aromatic ring. Sharing the negative charge over the ring increases the stability of the phenoxide
anion and thus increases the tendency of the corresponding phenol to dissociate (Figure ).
Figure: A resonance-stabilized phenoxide ion is more stable than an alkoxide ion.
Electrostatic potential maps show how the negative charge is more concentrated on
oxygen in the methoxide ion but is less concentrated on the phenoxide oxygen.
More stable
Less stable

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Most phenols, however, are not soluble in aqueous sodium bicarbonate (NaHCO3), but
carboxylic acids are soluble. Thus, aqueous NaHCO3 provides a method for distinguishing and
separating most phenols from carboxylicacids.

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