The mechanism of the Fischer esterification was controversial until 1938, when IrvingRoberts and Harold Urey of Columbia University used isotopic labeling to follow thealcohol oxygen atom through the reaction. A catalytic amount of sulfuric acid was addedto a mixture of 1 mole of acetic acid and 1 mole of special methanol containing the heavy18O isotope of oxygen. After a short period, the acid was neutralized to stop the reaction,and the components of the mixture were separated.H2SO4OCH3 C O H CH3 O H CH3 C O CH3 H2OO18 + +(a) Propose a mechanism for this reaction.(b) Follow the labeled 18O atom through your mechanism, and show where it is found inthe products.(c) The 18O isotope is not radioactive. Suggest how you could experimentally determinethe amounts of 18O in the separated components of the mixture

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Chapter1: Chemical Foundations
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The mechanism of the Fischer esterification was controversial until 1938, when Irving
Roberts and Harold Urey of Columbia University used isotopic labeling to follow the
alcohol oxygen atom through the reaction. A catalytic amount of sulfuric acid was added
to a mixture of 1 mole of acetic acid and 1 mole of special methanol containing the heavy
18O isotope of oxygen. After a short period, the acid was neutralized to stop the reaction,
and the components of the mixture were separated.
H2SO4
O
CH3 C O H CH3 O H CH3 C O CH3 H2O
O
18 + +
(a) Propose a mechanism for this reaction.
(b) Follow the labeled 18O atom through your mechanism, and show where it is found in
the products.
(c) The 18O isotope is not radioactive. Suggest how you could experimentally determine
the amounts of 18O in the separated components of the mixture

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