Part A Why do the nitro groups change the relative leaving tendencies of the car

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Part A Why do the nitro groups change the relative leaving tendencies of the carboxy and 2,4-dinitrophenoxy groups in the tetrahedral intermediate in the reaction below? 02 CHC-O CH.COHO CH ug When there are no nitro substituents on the aromatic ring, the carboxylate ion is a weaker base (a poorer leaving group) than the 2,4-dinitrophenolate ion, so the tetrahedral intermediate reforms the anhydride. In contrast, the 2,4-dinitrophenolate ion is a weaker base (a poorer leaving group) than the carboxylate ion, so the tetrahedral intermediate forms the ester. When there are no nitro substituents on the aromatic ring, the carboxylate ion is a weaker base (a better leaving group) than the 24-dinitrophenolate ion, so the tetrahedral intermediate reforms the ester. In contrast, the 2,4-dinitrophenolate ion is a weaker base (a better leaving group) than the carboxylate ion, so the tetrahedral intermediate forms the anhydride. When there are no nitro substituents on the aromatic ring, the carboxylate ion is a stronger base (a poorer leaving group) than the 2,4-dinitrophenolate ion, so the tetrahedral intermediate reforms the ester. In contrast, the 2,4-dinitrophenolate ion is a stronger base (a poorer leaving group) than the carboxylate ion, so the tetrahedral intermediate forms the anhydride. When there are no nitro substituents on the aromatic ring, the carboxylate ion is a stronger base (a better leaving group) than the 2,4-dinitrophenolate ion, so the tetrahedral intermediate reforms the anhydride. In contrast, the 2,4-dinitrophenolate ion is a stronger base (a better leaving group) than the carboxylate ion, so the tetrahedral intermediate forms the ester. Submit My Answers Give Up Continue

Explanation / Answer

2 option is correct. i.e.

When there are no nitro sustituents on the aromatic ring, the carboxylate ion is a weaker base (a better leaving group) than the 2,4-dinitrophenolate ion, so the tetrahedral intermediate reforms the ester. In contrast, the 2,4-dinitro phenolate ion is a weaker base (a better leaving group) than the carboxylate ion, so the tetrahedral intermediate reforms the anhydride.

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