a. When a carboxylic acid is dissolved in isotopically labeled water (H 2 18 O) and an

Chapter 16, Problem 64

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a. When a carboxylic acid is dissolved in isotopically labeled water (H 2 18 O) and an acid catalyst is added, the label is incorporated into both oxygens of the acid. Propose a mechanism to account for this. + H2O CH3 OH 18 + H2O CH3 OH 18 18 C O C O HCl b. If a carboxylic acid is dissolved in isotopically labeled methanol (CH 3 18 OH) and an acid catalyst is added, where will the label reside in the product? c. If an ester is dissolved in isotopically labeled water (H 2 18 O) and an acid catalyst is added, where will the label reside in the product?

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