Acid Chlorides

Acid chlorides are much more reactive than their carboxylic acid counterparts. Therefore, they are often preferred for industrial processes.

Functional Group and Nomenclature

The suffix for acid chlorides is "-anoyl chloride"/

The functional group is always on the terminal carbon (numbered as "1").

Preparation

Acid chlorides are prepared by reacting a carboxylic acid with thionyl chloride:

Reactions

All reactions of acid chlorides produce HCl gas as a byproduct, except amide formation (which only liberates HCl gas when a primary amide is made, with heat provided).

WITH WATER

Acid chlorides do not dissolve in water because they react with water molecules instead:

ESTERIFICATION

Acid chlorides are a very efficient way to make esters, because the reaction is not reversible:

AMIDE FORMATION

Reacting with ammonia and heat will produce a primary amide, with ammonium chloride as a byproduct.

Reacting with amines will produce secondary and tertiary amides, with an amino salt as a byproduct.