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Concept
Α,β-Unsaturated carbonyl compound
Summary
α,β-Unsaturated carbonyl compounds are organic compounds with the general structure (O=CR)−Cα=Cβ-R. Such compounds include enones and enals. In these compounds the carbonyl group is conjugated with an alkene (hence the adjective unsaturated). Unlike the case for carbonyls without a flanking alkene group, α,β-unsaturated carbonyl compounds are susceptible to attack by nucleophiles at the β-carbon. This pattern of reactivity is called vinylogous. Examples of unsaturated carbonyls are acrolein (propenal), mesityl oxide, acrylic acid, and maleic acid. Unsaturated carbonyls can be prepared in the laboratory in an aldol reaction and in the Perkin reaction.
α,β-Unsaturated carbonyl compounds can be subclassified according to the nature of the carbonyl and alkene groups.
File:MVK-2D-skeletal.png|[[Methyl vinyl ketone]], the simplest α,β-unsaturated ketone
File:Acrolein-skeletal.png|[[Acrolein]], the simplest α,β-unsaturated aldehyde
File:Methyl acrylate.png|[[Methyl acrylate]], an α,β-unsaturated ester
File:Acrylamide-2D-skeletal.png|[[Acrylamide]], precursor to polyacrylamide
File:Maleinsäure.svg|[[Maleic acid]], an α,β-unsaturated ''di''carbonyl
File:Fumaric-acid-2D-skeletal.png|[[Fumaric acid]], isomeric with maleic acid
File:Acryloyl chloride2.png|[[Acryloyl chloride]]
File:Chalcone.svg|[[Chalcone]]
α,β-Unsaturated carbonyl compounds featuring a carbonyl conjugated to an alkene that is terminal, or vinylic, contain the acryloyl group (H2C=CH−C(=O)−); it is the acyl group derived from acrylic acid. The preferred IUPAC name for the group is prop-2-enoyl, and it is also known as acrylyl or simply (and incorrectly) as acryl. Compounds containing an acryloyl group can be referred to as "acrylic compounds".
An α,β-unsaturated acid is a type of α,β-unsaturated carbonyl compound that consists of an alkene conjugated to a carboxylic acid. The simplest example is acrylic acid (CH2=CHCO2H). These compounds are prone to polymerization, giving rise to the large area of polyacrylate plastics. Acrylate polymers are derived from but do not contain the acrylate group.
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