organic chemistry Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J ...

, a vinyl group (abbr. Vi; IUPAC name: ethenyl group) is a

functional group In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the r ...

with the formula . It is the

ethylene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds). Ethylene ...

(IUPAC name: ethene) molecule () with one fewer

hydrogen Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula . It is colorless, odorless, tasteless, non-to ...

atom. The name is also used for any compound containing that group, namely where R is any other group of atoms. An industrially important example is

vinyl chloride Vinyl chloride is an organochloride with the formula H2C=CHCl. It is also called vinyl chloride monomer (VCM) or chloroethene. This colorless compound is an important industrial chemical chiefly used to produce the polymer polyvinyl chloride (PVC ...

, precursor to PVC, a plastic commonly known as ''vinyl''. Rollup chessboard

Vinyl is one of the

alkenyl In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, a ...

functional groups. On a carbon skeleton, sp²-hybridized carbons or positions are often called vinylic.

Allyl In organic chemistry, an allyl group is a substituent with the structural formula , where R is the rest of the molecule. It consists of a methylene bridge () attached to a vinyl group (). The name is derived from the scientific name for garlic, ...

s, acrylates and

styrenic Styrene () is an organic compound with the chemical formula C6H5CH=CH2. This derivative of benzene is a colorless oily liquid, although aged samples can appear yellowish. The compound evaporates easily and has a sweet smell, although high concen ...

s contain vinyl groups. (A styrenic crosslinker with two vinyl groups is called '' divinyl benzene''.)

Vinyl polymers

Vinyl groups can polymerize with the aid of a radical initiator or a catalyst, forming

vinyl polymer In polymer chemistry, vinyl polymers are a group of polymers derived from substituted vinyl () monomers. Their backbone is an extended alkane chain . In popular usage, "vinyl" refers only to polyvinyl chloride (PVC). Examples Vinyl polymers ...

s. Vinyl polymers contain no vinyl groups. Instead they are saturated. The following table gives some examples of vinyl polymers.

Reactivity

Vinyl derivatives are

alkene In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic ...

s. If activated by an adjacent group, the increased polarization of the bond gives rise to characteristic reactivity, which is termed vinylogous: * In

allyl In organic chemistry, an allyl group is a substituent with the structural formula , where R is the rest of the molecule. It consists of a methylene bridge () attached to a vinyl group (). The name is derived from the scientific name for garlic, ...

compounds, where the next carbon is saturated but substituted once,

allylic rearrangement An allylic rearrangement or allylic shift is an organic reaction in which the double bond in an allyl chemical compound shifts to the next carbon atom. It is encountered in nucleophilic substitution. In reaction conditions that favor a SN1 react ...

and related reactions are observed. ** Allyl

Grignard reagent A Grignard reagent or Grignard compound is a chemical compound with the general formula , where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride and phenylmagnesium bromide . ...

s (organomagnesiums) can attack with the vinyl end first. * If next to an electron-withdrawing group, conjugate addition (Michael addition) can occur. Vinyl organometallics, e.g.

vinyllithium Vinyllithium is an organolithium compound with the formula LiC2H3. A colorless or white solid, it is encountered mainly as a solution in tetrahydrofuran (THF). It is a reagent in synthesis of organic compounds.. Preparation and structure So ...

and

vinyl tributyltin Vinyl tributyltin is an organotin compound with the formula Bu3SnCH=CH2 (Bu = butyl). It is a white, air-stable solid. It is used as a source of vinyl anion equivalent in Stille coupling reactions. As a source of vinyltin reagents, early work us ...

, participate in coupling reactions such as in Negishi coupling.

Etymology

The

etymology Etymology () The New Oxford Dictionary of English (1998) – p. 633 "Etymology /ˌɛtɪˈmɒlədʒi/ the study of the class in words and the way their meanings have changed throughout time". is the study of the history of the form of words ...

of ''vinyl'' is the

Latin Latin (, or , ) is a classical language belonging to the Italic languages, Italic branch of the Indo-European languages. Latin was originally a dialect spoken in the lower Tiber area (then known as Latium) around present-day Rome, but through ...

''vinum'' = "

wine Wine is an alcoholic drink typically made from Fermentation in winemaking, fermented grapes. Yeast in winemaking, Yeast consumes the sugar in the grapes and converts it to ethanol and carbon dioxide, releasing heat in the process. Different ...

", and the Greek word "hylos" 'υλος (matter or material), because of its relationship with ethyl alcohol. The term "vinyl" was coined by the German chemist Hermann Kolbe in 1851.H. Kolbe (1851)
"On the chemical constitution and nature of organic radicals,"
''The Quarterly Journal of the Chemical Society of London'', 3 (4) : 369-405; see footnote o
page 376.
/ref>

References

{{Functional group Alkenyl groups Monomers Functional groups

Vinyl polymers

Reactivity

Etymology

See also

References