Why does the carboxylate ion () exhibit greater thermodynamic stability than the corresponding undis — GOC and Organic Chemistry Basics Chemistry Question
Question
Why does the carboxylate ion ($RCOO^-$) exhibit greater thermodynamic stability than the corresponding undissociated carboxylic acid ($RCOOH$), despite the acid being a neutral molecule?
Answer: B
💡 Solution & Explanation
In the carboxylate ion, the resonance creates two identical and equivalent canonical structures where the negative charge is equally shared by two electronegative oxygen atoms. Equivalent resonating structures provide massive stability. The acid generates unequal structures with charge separation.
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