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

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

functional group In organic chemistry, a functional group is any substituent or moiety (chemistry), moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions 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 bond, carbon–carbon doub ...

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

hydrogen Hydrogen is a chemical element; it has chemical symbol, symbol H and atomic number 1. It is the lightest and abundance of the chemical elements, most abundant chemical element in the universe, constituting about 75% of all baryon, normal matter ...

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

Vinyl is one of the alkenyl 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 . It consists of a methylene bridge () attached to a vinyl group (). The name is derived from the scientific name for garlic, . In 1844, Theodor Wertheim isolated a ...

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

Vinyl polymers

Vinyl groups can

polymerize In polymer chemistry, polymerization (American English), or polymerisation (British English), is a process of reacting monomer molecules together in a chemical reaction to form polymer chains or three-dimensional networks. There are many form ...

with the aid of a radical initiator or a catalyst, forming vinyl polymers. Vinyl polymers contain no vinyl groups. Instead they are saturated. The following table gives some examples of vinyl polymers.

Synthesis and reactivity

Vinyl derivatives are

alkene In organic chemistry, an alkene, or olefin, is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or at the terminal position. Terminal alkenes are also known as Alpha-olefin, α-olefins. The Internationa ...

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 . It consists of a methylene bridge () attached to a vinyl group (). The name is derived from the scientific name for garlic, . In 1844, Theodor Wertheim isolated a ...

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

allylic rearrangement An allylic rearrangement or allylic shift is an organic reaction, organic chemical reaction in which reaction at a center Vicinal (chemistry), vicinal to a double bond causes the double bond to shift to an adjacent pair of atoms: It is encountered ...

and related reactions are observed. ** Allyl

Grignard reagent Grignard reagents or Grignard compounds are chemical compounds 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 bromi ...

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 vinylations 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 Atomic mass ( or ) is the mass of a single atom. The atomic mass mostly comes from the combined mass of the protons and neutrons in the nucleus, with minor contributions from the electrons and nuclear binding energy. The atomic mass of atoms, ...

of carbon it was believed to be at the time. Then in 1839 it was renamed by

Justus von Liebig Justus ''Freiherr'' von Liebig (12 May 1803 – 18 April 1873) was a Germans, German scientist who made major contributions to the theory, practice, and pedagogy of chemistry, as well as to agricultural and biology, biological chemistry; he is ...

to "

acetyl In organic chemistry, an acetyl group is a functional group denoted by the chemical formula and the structure . It is sometimes represented by the symbol Ac (not to be confused with the element actinium). In IUPAC nomenclature, an acetyl grou ...

", because he believed it to be the radical of the

acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main compone ...

. The modern term was coined by German chemist Hermann Kolbe in 1851, who rebutted Liebig's hypothesis.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> However even in 1860 Marcellin Berthelot still based the name he coined for

acetylene Acetylene (Chemical nomenclature, systematic name: ethyne) is a chemical compound with the formula and structure . It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is u ...

on Liebig's nomenclature and not on Kolbe's. The

etymology Etymology ( ) is the study of the origin and evolution of words—including their constituent units of sound and meaning—across time. In the 21st century a subfield within linguistics, etymology has become a more rigorously scientific study. ...

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 spoken by the Latins (Italic tribe), Latins in Latium (now known as Lazio), the lower Tiber area aroun ...

''vinum'' = "

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

", and the Greek word "hylos" 'υλος (matter or material), because of its relationship with

ethyl alcohol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an alcohol, with its formula also written as , or EtOH, where Et is the pseudoelement symbol ...

References

{{Functional group Alkenyl groups Monomers Functional groups

Vinyl polymers

Synthesis and reactivity

History and etymology

See also

References