Question
Sodium acetate reacts with 4-nitrophenyl benzoates to give mixed anhydrides when the reaction is conducted in a polar aprotic solvent in the presence of a crown ether. The reaction is strongly accelerated by a quaternary nitrogen substituent in the ortho position. Suggest an explanation for this substituent effect.
Step 1
Sodium acetate (NaOAc) is a nucleophile, and 4-nitrophenyl benzoate is an electrophile. In the presence of a crown ether, the sodium ion (Na+) is complexed, which increases the nucleophilicity of the acetate ion (OAc-). Show more…
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