GOC and Organic Chemistry BasicshardMCQ MULTIPLE

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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