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Ch.21 - Organic Chemistry
Chapter 21, Problem 103

Explain why carboxylic acids are much stronger acids than alcohols.

Verified step by step guidance
1
Carboxylic acids and alcohols both contain an -OH group, but the key difference lies in the structure and stability of their conjugate bases.
When a carboxylic acid donates a proton (H+), it forms a carboxylate ion, which is resonance-stabilized. This means the negative charge can be delocalized over two oxygen atoms, making the conjugate base more stable.
In contrast, when an alcohol donates a proton, it forms an alkoxide ion, which lacks resonance stabilization. The negative charge is localized on the oxygen atom, making the conjugate base less stable.
The greater stability of the carboxylate ion compared to the alkoxide ion means that carboxylic acids are more willing to donate a proton, thus making them stronger acids.
Additionally, the presence of the carbonyl group (C=O) in carboxylic acids can further stabilize the conjugate base through inductive effects, enhancing the acid strength compared to alcohols.