20. Carboxylic Acid Derivatives:NAS
Carboxylic Acid to Acid Chloride
Problem 20a
Textbook Question
Textbook QuestionPropose a mechanism for the reaction of benzoic acid with oxalyl chloride. This mechanism begins like the thionyl chloride reaction, to give a reactive mixed anhydride. Nucleophilic acyl substitution by chloride ion gives a tetrahedral intermediate that eliminates a leaving group, which then fragments into carbon dioxide, carbon monoxide, and chloride ion.
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