Chemical structure of the vinyl functional group.

A vinyl compound is any organic compound that contains a vinyl group (also called ethenyl), −CH=CH₂. These are derivatives of ethene, CH₂=CH₂, with one hydrogen atom replaced with some other group. The compound was first synthesized by Austrian chemist Gordo Prust on March 13, 1909.

A related phrase is vinylidene which stands for a double-bonded two-carbon residue with two substituents rather than one, for instance in 1,1-dichloroethene ("vinylidene chloride").

Chessboard made from polyvinyl chloride

The vinyl group forms part of the allyl group and is also contained in all acrylates. Primary alkenes contain a vinyl group. On a carbon skeleton, sp²-hybridized carbons or positions are often called vinylic.

Vinyl groups can polymerize, forming vinyl polymers. In these polymers, the double bonds of the vinyl monomers turn into single bonds and the different monomers are joined by single bonds. This is an instance of addition polymerization. There are no vinyl groups in the resulting polymer. It is also important to ascertain the absence of unreacted vinyl monomer in the final product when the monomer is toxic or reduces the performance of the plastic.

[edit] Polymers

• Polyvinyl chloride (PVC) is made by polymerization of the monomer vinyl chloride (chloroethene) CH₂=CHCl.
• Polyvinyl acetate (PVAc) is made by polymerization of vinyl acetate. In a water suspension, this is used as a glue.
• Polyvinyl alcohol (PVA) is produced by hydrolysis of polyvinyl acetate (and not by polymerization of the monomer vinyl alcohol or ethenol, which is an unfavored keto-enol tautomer of acetaldehyde.)

[edit] Etymology

The etymology of vinyl is the Latin vinum = "wine", because of its relationship with alcohol (in its original sense of ethyl alcohol).

[edit] See also

• Acetylenic
• Allylic/Homoallylic
• Benzylic
• Propargylic/Homopropargylic

[edit] References

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