Acid Chlorides or Acyl Chlorides : Acid Chlorides Manufacturers
Acyl Chloride: Reactions & Synthesis Acyl Chlorides and Related Functional GroupsAcid Chlorides, sometimes called acid chlorides, are often smelly organic compounds that are very reactive. The term acyl chloride describes a functional group containing a carbonyl group (C=O) and a chlorine atom (Cl). Molecules containing this functional group can be referred to as acyl chlorides themselves. They are used in organic synthesis to convert carboxylic acids into other functional groups because of their high reactivity.
Remember, a functional group is simply an arrangement of atoms in a particular orientation on a molecule. Some of the atoms in a functional group can have multiple bonds to them. The functional groups that are most important in this lesson are carboxylic acid, acyl chloride, acid anhydride, ester and amide:
Carboxylic acid functional group and derivative functional groups
Notice that each of these functional groups contains a carbonyl group (a carbon double bonded to an oxygen). If there is an OH group next to the carbonyl group, the molecule is a carboxylic acid; if there is a Cl atom, the molecule is an acyl chloride.
Acyl Chlorides in Synthesis
Acyl chlorides, acid anhydrides (or just 'anhydrides'), esters, and amides are all derivatives of carboxylic acids, but it is difficult to make them directly from this functional group. This is because the OH group in the carboxylic acid is hard to replace with a new group; carboxylic acids are not very reactive in this way. By converting a carboxylic acid to the more reactive acyl chloride, we can then synthesize many carboxylic acid derivatives.
Acyl Chloride Formation
Let's put on our safety glasses and check out some of the reactions we can do in the lab involving acyl chlorides. First of all, carboxylic acids can be made into acyl chlorides by treatment with thionyl chloride. Make sure you have good ventilation, because thionyl chloride is one smelly compound! The reaction looks like this:
Reaction of a carboxylic acid to form an acyl chloride
Notice in the reaction intermediate shown in braces that the oxygen atom of the carboxylic acid becomes attached to the sulfur atom of thionyl chloride. A reaction intermediate is formed when reactions have multiple distinct steps on the way to forming the product. To form the intermediate shown, one chlorine atom leaves the thionyl chloride molecule. The intermediate contains a good leaving group, which are the pieces of the molecule that are able to depart the molecule because they are relatively stable on their own. When the intermediate is converted to the product, the chlorine atom that was released in the first step comes back and replaces the sulfur-containing leaving group, forming the acid chloride.
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