20.13Because ester hydrolysis in base proceeds by acyl–oxygen cleavage, the 18O label becomes incorporated into acetate ion .20.14Step 1: Nucleophilic addition of hydroxide ion to the carbonyl groupStep 2: Proton transfer from water to give neutral form of tetrahedral intermediateStep 3: Dissociation of tetrahedral intermediateStep 4: Proton transfer from benzoic acid20.15The starting material is a lactone, a cyclic ester. The ester function is converted to an amide bynucleophilic acyl substitution.Methylamine4-Pentanolide4-Hydroxy-N-methylpentanamide1CH3NH2OCH3OCH3NHCCH2CH2CHCH3OHOBenzoic acidHydroxideionOC6H5COH1WaterBenzoate ion2C6H5CO1HO2111Tetrahedral intermediate
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This note was uploaded on 09/30/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.