Whish among -phenol and carboxylic acid- is more acidic? Why?

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Solution

Carboxylic acids have an extra oxygen nearby. This oxygen is pulling on the covalent electrons at the OH-group and making it weaker.

Another factor is that the carboxylic acid ion has a resonance form, promoting stability within the molecule. The corresponding carbo-cation that forms when an alcohol loses a hydrogen does not have this resonance form an is highly reactive.

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