 Solution

ID: past-exam-of-the-chemistry-course-of-the-year-3-of-the-natural-sciences-course-of-the-university-of-cambridge/2022/paper-4/66/a/i/solution

For the ordinary esters, hydroxide adds to the acyl carbon, producing a tetrahedral oxyanion; collapse expels 2,4-dinitrophenoxide, followed by acid-base equilibration to the benzoate. This is base-promoted acyl-oxygen cleavage, a BAC2 mechanism. Rate-limiting addition naturally gives the observed bimolecular dependence on ester and OH

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