Acyl chloride

An acyl chloride is a carboxylic acid derivative with chlorine bonded to the carbonyl carbon. Its reactive acyl group readily transfers to nucleophiles.

Nucleophilic acyl substitution: A reaction in which a nucleophile replaces a leaving group attached to an acyl carbon. Acyl chlorides commonly react by addition to the carbonyl followed by chloride elimination.
Acyl group: A group derived from a carboxylic acid by removing its hydroxyl group. An acyl chloride consists of this group bonded to chlorine.
Amide: A carboxylic acid derivative in which nitrogen is bonded to the acyl carbon. Ammonia and amines react with acyl chlorides to form amides.
Carboxylic acid ester: A carboxylic acid derivative in which the acyl carbon is bonded to an oxygen-linked carbon group. Esters are generally less reactive toward nucleophilic acyl substitution than acyl chlorides.
Acylation: The introduction of an acyl group into a molecule. Replacing chloride with a nucleophile transfers the acyl group to that molecule.
Carboxylic acid: An organic compound containing a carboxyl group, –COOH. Replacing its hydroxyl group with chlorine gives the acyl chloride structure.
Ester: A carboxylic acid derivative containing an acyl–oxygen–carbon linkage. Alcohols react with acyl chlorides to produce esters.
Carboxamide: A carboxylic acid derivative in which nitrogen is bonded directly to the acyl carbon. Amides are less reactive because nitrogen donates electron density and is a poor leaving group.
Friedel–Crafts acylation: An electrophilic aromatic substitution that installs an acyl group on an aromatic ring. Acyl chlorides supply acyl electrophiles in the classic Lewis-acid-promoted reaction.
Carbonyl group: A functional group consisting of a carbon atom double-bonded to oxygen. The carbonyl bond makes the acyl carbon susceptible to nucleophilic attack.

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