Which of the following compounds possess an overall thermodynamic acidic strength greater than that — GOC and Organic Chemistry Basics Chemistry Question
Question
Which of the following compounds possess an overall thermodynamic acidic strength greater than that of unsubstituted benzoic acid ($C_6H_5COOH$)?
Answer: A,B,C
💡 Solution & Explanation
Formic acid is stronger than benzoic acid due to the destabilizing $+R$ effect of the phenyl ring in the latter. Salicylic acid is exceptionally strong due to stabilization of the conjugate base via intramolecular hydrogen bonding (ortho-effect). Picric acid is highly acidic ($pKa \approx 0.71$) due to three strong $-M$ and $-I$ nitro groups. p-Anisic acid is weaker due to the electron-donating $+M$ effect of the methoxy group.
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