Editing Vinyl group

{{Short description|1=Chemical group (–CH=CH₂)}}
{{For-multi|the music technology company|Vinyl Group|the carbocation|Vinyl cation|6=Vinyl (disambiguation){{!}}Vinyl}}
[[File:Vinyl group.png|thumb|100px|right|Chemical structure of the vinyl functional group.]]

In [[organic chemistry]], a '''vinyl group''' (abbr. '''Vi''';<ref>Rules for abbreviation of protecting groups [http://iupac.org/publications/pac/pdf/2013/pdf/8501x0307.pdf p.310]</ref> [[IUPAC name]]: '''ethenyl group'''<ref>IUPAC Provisional Recommendations 2004 [http://old.iupac.org/reports/provisional/abstract04/BB-prs310305/Chapter5.pdf Chapter 5]</ref>) is a [[functional group]] with the formula {{chem2|\sCH\dCH2}}.  It is the [[ethylene]] (IUPAC name: ethene) molecule ({{chem2|H2C\dCH2}}) with one fewer [[hydrogen]] atom.  The name is also used for any compound containing that group, namely {{chem2|R\sCH\dCH2}} where R is any other group of atoms.

An industrially important example is [[vinyl chloride]], precursor to [[polyvinyl chloride|PVC]],<ref name="Endo-2002">{{cite journal |last1=Endo |first1=Kiyoshi |title=Synthesis and structure of poly(vinyl chloride) |journal=Progress in Polymer Science |date=December 2002 |volume=27 |issue=10 |pages=2021–2054 |doi=10.1016/S0079-6700(02)00066-7}}</ref> a plastic commonly known as ''vinyl''. 

[[File:Rollup chessboard.jpg|right|thumb|[[Chessboard]] made from [[polyvinyl chloride]]]]

Vinyl is one of the [[alkenyl]] functional groups. On a carbon skeleton, [[Orbital hybridisation#sp2|sp<sup>2</sup>-hybridized]] carbons or positions are often called '''vinylic'''. [[Allyl]]s, [[acrylate]]s and [[styrenic]]s contain vinyl groups. (A styrenic crosslinker with two vinyl groups is called ''[[divinyl benzene]]''.)

==Vinyl polymers==

{{main|Vinyl polymer}}

Vinyl groups can [[polymerization|polymerize]] with the aid of a radical initiator or a catalyst, forming [[vinyl polymer]]s. Vinyl polymers contain no vinyl groups.  Instead they are saturated. The following table gives some examples of vinyl polymers.

{| class="wikitable"
|-
! Monomer example !! Example of resulting polymer
|-
| [[Vinyl chloride]] || [[Polyvinyl chloride]] (PVC)
|-
|  [[Vinyl fluoride]] || [[Polyvinyl fluoride]] (PVF)
|-
|  [[Vinyl acetate]] || [[Polyvinyl acetate]] (PVAc)
|}

==Synthesis and reactivity==
Vinyl derivatives are [[alkene]]s.  If activated by an adjacent group, the increased polarization of the bond gives rise to characteristic reactivity, which is termed [[vinylogous]]:
* In [[allyl]] compounds, where the next carbon is saturated but substituted once, [[allylic rearrangement]] and related reactions are observed.
** Allyl [[Grignard reagent]]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]] and [[vinyl tributyltin]], participate in [[vinylation]]s including coupling reactions such as in [[Negishi coupling]].

==History and etymology==
The radical was first reported by [[Henri Victor Regnault]] in 1835 and initially named ''aldehydène''. Due to the incorrect measurement of the [[atomic mass]] of carbon it was believed to be {{chem2|C4H6}} at the time. Then in 1839 it was renamed by [[Justus von Liebig]] to "[[acetyl]]", because he believed it to be the radical of the [[acetic acid]].<ref>{{Cite journal |last1=Constable |first1=Edwin C. |last2=Housecroft |first2=Catherine E. |date=2020-04-20 |title=Before Radicals Were Free – the Radical Particulier of de Morveau |journal=Chemistry |language=en |volume=2 |issue=2 |pages=293–304 |doi=10.3390/chemistry2020019 |issn=2624-8549|doi-access=free }}</ref>

The modern term was coined by German chemist [[Hermann Kolbe]] in 1851, who rebutted Liebig's hypothesis.<ref>H. Kolbe (1851), [https://books.google.com/books?id=jJ8wAAAAYAAJ&pg=PA369 "On the chemical constitution and nature of organic radicals,"] ''The Quarterly Journal of the Chemical Society of London'', '''3''' (4) :  369-405; see footnote on [https://books.google.com/books?id=jJ8wAAAAYAAJ&pg=PA376 page 376.]</ref> However even in 1860 [[Marcellin Berthelot]] still based the name he coined for [[acetylene]] on Liebig's nomenclature and not on Kolbe's.

The [[etymology]] of "vinyl" is the [[Latin]] ''vinum'' = "[[wine]]", and the [[Greek language |Greek]] word "hylos" 'υλος (matter or material), because of its relationship with [[Ethanol|ethyl alcohol]].

==See also==
* [[Acetylenic]]
* [[Allylic|Allylic/Homoallylic]]
* [[Alpha-olefin]]
* [[Benzyl#Benzylic position|Benzylic]]
* [[Propargylic|Propargylic/Homopropargylic]]
* [[Vinylogous]]

== References ==
{{reflist}}

{{Functional group}}

[[Category:Alkenyl groups]]
[[Category:Monomers]]
[[Category:Functional groups]]