20.9The starting material contains three acetate ester functions. All three undergo hydrolysis in aqueoussulfuric acid.The product is 1,2,5-pentanetriol. Also formed in the hydrolysis of the starting triacetate are threemolecules of acetic acid.20.10Step 1: Protonation of the carbonyl oxygenStep 2: Nucleophilic addition of waterStep 3: Deprotonation of oxonium ion to give neutral form of tetrahedral intermediateStep 4: Protonation of ethoxy oxygen1Oxonium ionC6H5COCH2CH3OHHOH1OHHWater1C6H5COCH2CH3OHHOTetrahedralintermediateOHHH1Hydroniumion1OHH1C6H5COCH2CH3OHO1HHC6H5COCH2CH3OH
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