The mechanism for hydrolysis of an ester in aqueous acid involves formation of a tetrahedral carbonyl addition intermediate. Evidence in support of this mechanism comes from an experiment designed by Myron Bender. He first prepared ethyl benzoate enriched with oxygen-18 in the carbonyl oxygen and then carried out acid-catalyzed hydrolysis of the ester in water containing no enrichment in oxygen-18. If he stopped the experiment after only partial hydrolysis and isolated the remaining ester, the recovered ethyl benzoate lost a portion of its enrichment in oxygen-18. In other words, some exchange had occurred between oxygen-18 of the ester and oxygen-16 of water. Show how this observation bears on the formation of a tetrahedral carbonyl addition intermediate during acid-catalyzed ester hydrolysis.
The mechanism for hydrolysis of an ester in aqueous acid involves formation of a tetrahedral carbonyl addition intermediate. Evidence in support of this mechanism comes from an experiment designed by Myron Bender. He first prepared ethyl benzoate enriched with oxygen-18 in the carbonyl oxygen and then carried out acid-catalyzed hydrolysis of the ester in water containing no enrichment in oxygen-18. If he stopped the experiment after only partial hydrolysis and isolated the remaining ester, the recovered ethyl benzoate lost a portion of its enrichment in oxygen-18. In other words, some exchange had occurred between oxygen-18 of the ester and oxygen-16 of water. Show how this observation bears on the formation of a tetrahedral carbonyl addition intermediate during acid-catalyzed ester hydrolysis.
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