a) Write a mechanism for the esterifi cation of propanoic acid with 18O-labeled ethanol

Chapter 19, Problem 39

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a) Write a mechanism for the esterifi cation of propanoic acid with 18O-labeled ethanol. Showclearly the fate of the 18O label. (b) Acid-catalyzed hydrolysis of an unlabeled ester with18O-labeled water (H218O) leads to incorporation of some 18O into both oxygens of the carboxylicacid product. Explain by a mechanism. (Hint: You must use the fact that all steps in the mechanismare reversible.)2.4 2.2 2.0 1.8 1.6300-MHz 1H NMR spectrum ppm ()1H NMRIR-GIRTransmittance (%)100Wavenumber

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