Vinyl group

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Chemical structure of the vinyl functional group. Vinyl group.png
Chemical structure of the vinyl functional group.

In organic chemistry, a vinyl group (abbr. Vi; [1] IUPAC name: ethenyl group [2] ) is a functional group with the formula −CH=CH2. It is the ethylene (IUPAC name: ethene) molecule (H2C=CH2) with one fewer hydrogen atom. The name is also used for any compound containing that group, namely R−CH=CH2 where R is any other group of atoms.

Contents

An industrially important example is vinyl chloride, precursor to PVC, [3] a plastic commonly known as vinyl.

Chessboard made from polyvinyl chloride Rollup chessboard.jpg
Chessboard made from polyvinyl chloride

Vinyl is one of the alkenyl functional groups. On a carbon skeleton, sp2-hybridized carbons or positions are often called vinylic. Allyls, acrylates and styrenics 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 polymers. Vinyl polymers contain no vinyl groups. Instead they are saturated. The following table gives some examples of vinyl polymers.

Monomer exampleExample of resulting polymer
Vinyl chloride Polyvinyl chloride (PVC)
Vinyl fluoride Polyvinyl fluoride (PVF)
Vinyl acetate Polyvinyl acetate (PVAc)

Synthesis and reactivity

Vinyl derivatives are alkenes. If activated by an adjacent group, the increased polarization of the bond gives rise to characteristic reactivity, which is termed vinylogous:

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 of carbon it was believed to be 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. [4]

The modern term was coined by German chemist Hermann Kolbe in 1851, who rebutted Liebig's hypothesis. [5] 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 word "hylos" 'υλος (matter or material), because of its relationship with ethyl alcohol.

See also

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<span class="mw-page-title-main">Alkyne</span> Hydrocarbon compound containing one or more C≡C bonds

In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond. The simplest acyclic alkynes with only one triple bond and no other functional groups form a homologous series with the general chemical formula CnH2n−2. Alkynes are traditionally known as acetylenes, although the name acetylene also refers specifically to C2H2, known formally as ethyne using IUPAC nomenclature. Like other hydrocarbons, alkynes are generally hydrophobic.

<span class="mw-page-title-main">Carboxylic acid</span> Organic compound containing a –C(=O)OH group

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<span class="mw-page-title-main">Ketone</span> Organic compounds of the form >C=O

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<span class="mw-page-title-main">Aldehyde</span> Organic compound containing the functional group R−CH=O

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<span class="mw-page-title-main">Allyl group</span> Chemical group (–CH₂–CH=CH₂)

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<span class="mw-page-title-main">Allyl alcohol</span> Organic compound (CH2=CHCH2OH)

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<span class="mw-page-title-main">Organozinc chemistry</span>

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<span class="mw-page-title-main">Allyl bromide</span> Chemical compound

Allyl bromide (3-bromopropene) is an organic halide. It is an alkylating agent used in synthesis of polymers, pharmaceuticals, perfumes and other organic compounds. Allyl bromide is a colorless liquid, although commercial samples appear yellow or brown. It is an irritant and a potentially dangerous alkylating agent. Allyl bromide is more reactive but more expensive than allyl chloride, and these considerations guide its use.

Group 14 hydrides are chemical compounds composed of hydrogen atoms and group 14 atoms.

α,β-Unsaturated carbonyl compound Functional group of organic compounds

α,β-Unsaturated carbonyl compounds are organic compounds with the general structure (O=CR)−Cα=Cβ-R. Such compounds include enones and enals, but also carboxylic acids and the corresponding esters and amides. In these compounds, the carbonyl group is conjugated with an alkene. 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.

References

  1. Rules for abbreviation of protecting groups p.310
  2. IUPAC Provisional Recommendations 2004 Chapter 5
  3. Endo, Kiyoshi (December 2002). "Synthesis and structure of poly(vinyl chloride)". Progress in Polymer Science. 27 (10): 2021–2054. doi:10.1016/S0079-6700(02)00066-7.
  4. Constable, Edwin C.; Housecroft, Catherine E. (2020-04-20). "Before Radicals Were Free – the Radical Particulier of de Morveau". Chemistry. 2 (2): 293–304. doi: 10.3390/chemistry2020019 . ISSN   2624-8549.
  5. 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 on page 376.