JEE Main Chemistry question
Ethyl acetate labelled with the oxygen-18 isotope at its carbonyl oxygen, , is hydrolysed with aqueous NaOH (saponification). What is the mass number of the oxygen atom marked with an asterisk that ends up in the carboxylate product?
Answer: 18
Solution
Base-catalysed ester hydrolysis proceeds by hydroxide attacking the carbonyl carbon to form a tetrahedral intermediate, which then expels the alkoxy (ethoxide) oxygen, not the original carbonyl oxygen; this is "acyl-oxygen cleavage." The
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