Organic Chemistry: Concepts and Applications - Headley Allan D. 2020

Nucleophilic Substitution Reactions at Acyl Carbons
16.8 Substitution Reactions Involving Oxalyl Chloride

Oxalyl chloride is a unique organic compound that has adjacent carbonyl groups and chlorines bonded to each carbonyl carbon as shown below. These structural features make oxalyl chloride a very reactive compound, which is primarily used to convert carboxylic acids to acid chlorides. This reaction is a substitution reaction in which the ─OH group from the carboxylic acid is substituted with a chlorine from the oxalyl chloride. An example of this reaction is shown in Reaction (16-104).

(16-104)Image

A driving force for this reaction to proceed to give the products is that gaseous products are produced, an increase in entropy for the reaction.