ORGANIC CHEMISTRY II LAB MANUAL>CUSTOM<
ORGANIC CHEMISTRY II LAB MANUAL>CUSTOM<
9th Edition
ISBN: 9780534261641
Author: SIMEK
Publisher: Cengage Learning
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Chapter 20.15, Problem 20.22P

Propose 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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