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Problem- In the early days of studies of the mechanism of the hydroxide ion-promoted hydrolysis of ester, it was not clear which bond was broken- the acyl C-O bond or the akyl C-O bond. using ethyl benzoate labeled as shown below, which of the products would contain the 18O label if (a) the acyl C-O bond is broken and (b) the alkyl C-O bond is broken?

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