acid strength carboxylic vs alcohol

Question

Carboxylic acids are stronger acids than alcohols because:

RankGuru · Accepted Answer

1. **Acid Behavior**: $HA \rightleftharpoons H^+ + A^-$. Stability of $A^-$ (conjugate base) determines acid strength.
2. **Carboxylic Acid**: When it loses a proton, the **carboxylate ion** ($RCOO^-$) is formed.
3. **Resonance**: In carboxylate, the negative charge is delocalized over two highly electronegative oxygen atoms ($O \dot{-} C \dot{-} O$). These are equivalent structures, providing immense stabilization.
4. **Alcohol**: When it loses a proton, the **alkoxide ion** ($RO^-$) is formed. The charge is localized on a single oxygen atom and is actually destablized by the $+I$ effect of the alkyl group.
5. **Conclusion**: Greater stability of carboxylate makes carboxylic acids much stronger acids.

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acid strength carboxylic vs alcohol

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