Carboxylic Acid Chloride Reactions

You may use these summaries and problems but you may NOT download them for use at another site, nor may you charge for access to them. Copyright Linda M. Sweeting 1997

The following example reactions are organized by type, with references to text chapters. Links within these summaries (which may show up as boxes around reagents) will provide further information about the reagents and their other reactions. Return to Reaction Summaries menu for other functional group choices.

Note that products are shown after neutralization, and neutralization of products is NOT shown here for simplicity. Exception: acid-base reactions.

Anhydrides react in essentially the same way but yield one mole of the carboxylic acid instead of HCl as product. In addition, sulfonic, sulfuric, phosphoric, and other acid chlorides and anhydrides undergo analogous reactions to form esters, amides, etc.

Addition / Elimination Reactions

+ HCl
Mechanism!
McMurry 21.4, Fessenden 15.3C, Schmid 16.5
To other syntheses of acids

+ HCl
Mechanism!
McMurry 21.4, Fessenden 15.3C, Schmid 16.5
To other syntheses of esters

+ HCl
Schmid 16.5

+ NaCl
Mechanism!
McMurry 21.2, Fessenden 15.3C, 15.4B, Schmid 16.5

+ HCl
Mechanism!
McMurry 21.4, 24.9, Fessenden 15.3C, Schmid 16.5
To other syntheses of amides

+ HCl
Mechanism!
McMurry 21.4, 24.7, Fessenden 15.3C, Schmid 16.5
To other syntheses of amides

Addition / Reduction

Other reagents: NaBH₄
McMurry 21.4, Fessenden 15.3C, Schmid 16.12
To syntheses of alcohols

McMurry 21.4, Fessenden 15.3C, Schmid 16.14, A
To: Syntheses of aldehydes

Note that two moles of Grignard reagent are required to do this reaction. The product from addition of one mole of Grignard is a ketone which also reacts with Grignard. If two moles of Grignard are not present, incomplete reaction yields a mixture of products and starting materials.
McMurry 21.4, Fessenden 15.3C, Schmid 16.13
To: Synthesis of alcohols

McMurry 21.4. Fessenden 15.3C, Schmid 16.14, B
To: Synthesis of ketones

To main reactions menu
Last update Februrary 1999