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Vinyl

Vinyl

Overview
A vinyl compoundis any organic compound
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 that contains a vinyl group (Preferred IUPAC name
Preferred IUPAC name
In chemical nomenclature, a preferred IUPAC name is a unique name, assigned to a chemical substance and preferred among the possible names generated by IUPAC nomenclature. The "preferred IUPAC nomenclature" provides a set of rules for choosing between multiple possibilities in situations where it...

 ethenyl),
which are derivatives of ethene, CH2=CH2, with one hydrogen
Hydrogen
Hydrogen is the chemical element with atomic number 1. It is represented by the symbol H. With an average atomic weight of , hydrogen is the lightest and most abundant chemical element, constituting roughly 75% of the Universe's chemical elemental mass. Stars in the main sequence are mainly...

 atom replaced with some other group. An industrially important example is vinyl chloride
Vinyl chloride
Vinyl chloride is the 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 . At ambient pressure and temperature, vinyl chloride...

, precursor to PVC
Polyvinyl chloride
Polyvinyl chloride, commonly abbreviated PVC, is a thermoplastic polymer. It is a vinyl polymer constructed of repeating vinyl groups having one hydrogen replaced by chloride. Polyvinyl chloride is the third most widely produced plastic, after polyethylene and polypropylene. PVC is widely used in...

, a plastic commonly known as "vinyl".
Vinyl groups are alkene
Alkene
In organic chemistry, an alkene, olefin, or olefine is an unsaturated chemical compound containing at least one carbon-to-carbon double bond...

 derivatives: Primary alkenes contain vinyl groups. On a carbon skeleton, sp2-hybridized carbons or positions are often called vinylic.
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Encyclopedia
A vinyl compoundis any organic compound
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 that contains a vinyl group (Preferred IUPAC name
Preferred IUPAC name
In chemical nomenclature, a preferred IUPAC name is a unique name, assigned to a chemical substance and preferred among the possible names generated by IUPAC nomenclature. The "preferred IUPAC nomenclature" provides a set of rules for choosing between multiple possibilities in situations where it...

 ethenyl),
which are derivatives of ethene, CH2=CH2, with one hydrogen
Hydrogen
Hydrogen is the chemical element with atomic number 1. It is represented by the symbol H. With an average atomic weight of , hydrogen is the lightest and most abundant chemical element, constituting roughly 75% of the Universe's chemical elemental mass. Stars in the main sequence are mainly...

 atom replaced with some other group. An industrially important example is vinyl chloride
Vinyl chloride
Vinyl chloride is the 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 . At ambient pressure and temperature, vinyl chloride...

, precursor to PVC
Polyvinyl chloride
Polyvinyl chloride, commonly abbreviated PVC, is a thermoplastic polymer. It is a vinyl polymer constructed of repeating vinyl groups having one hydrogen replaced by chloride. Polyvinyl chloride is the third most widely produced plastic, after polyethylene and polypropylene. PVC is widely used in...

, a plastic commonly known as "vinyl".
Vinyl groups are alkene
Alkene
In organic chemistry, an alkene, olefin, or olefine is an unsaturated chemical compound containing at least one carbon-to-carbon double bond...

 derivatives: Primary alkenes contain vinyl groups. On a carbon skeleton, sp2-hybridized carbons or positions are often called vinylic. Allyl
Allyl
An allyl group is a substituent with the structural formula H2C=CH-CH2R, where R is the connection to the rest of the molecule. It is made up of a methylene , attached to a vinyl group . The name is derived from the Latin word for garlic, Allium sativum. Theodor Wertheim isolated an allyl...

s, acrylate
Acrylate
The acrylate ion is the ion of acrylic acid.Acrylates are the salts and esters of acrylic acid. They are also known as propenoates ....

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

Etymology


The etymology
Etymology
Etymology is the study of the history of words, their origins, and how their form and meaning have changed over time.For languages with a long written history, etymologists make use of texts in these languages and texts about the languages to gather knowledge about how words were used during...

 of vinyl is the Latin
Latin
Latin is an Italic language originally spoken in Latium and Ancient Rome. It, along with most European languages, is a descendant of the ancient Proto-Indo-European language. Although it is considered a dead language, a number of scholars and members of the Christian clergy speak it fluently, and...

 vinum = "wine
Wine
Wine is an alcoholic beverage, made of fermented fruit juice, usually from grapes. The natural chemical balance of grapes lets them ferment without the addition of sugars, acids, enzymes, or other nutrients. Grape wine is produced by fermenting crushed grapes using various types of yeast. Yeast...

", because of its relationship with alcohol
Alcohol
In chemistry, an alcohol is an organic compound in which the hydroxy functional group is bound to a carbon atom. In particular, this carbon center should be saturated, having single bonds to three other atoms....

 (in its original sense of ethyl alcohol
Ethanol
Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a psychoactive drug and one of the oldest recreational drugs. Best known as the type of alcohol found in alcoholic beverages, it is also used in thermometers, as a...

).

Related to vinyl compounds are vinylidenes. Vinylidene itself, a rare species of theoretical interest, is a modified carbene
Carbene
In chemistry, a carbene is a molecule containing a neutral carbon atom with a valence of two and two unshared valence electrons. The general formula is RR'C:, but the carbon can instead be double-bonded to one group. The term "carbene" may also merely refer to the compound H2C:, also called...

 with the formula CH2=C:. Vinylidenes describe compounds containing the functional group CX2=C. For example, 1,1-dichloroethene
1,1-Dichloroethene
1,1-Dichloroethene, commonly called 1,1-dichloroethylene or 1,1-DCE, is an organochloride with the molecular formula C2H2Cl2. It is a colorless liquid with a sharp odor. Like most chlorocarbons, it is poorly soluble in water, but soluble in organic solvents...

 (CH2=CCl2) is called vinylidene chloride.

Vinyl and vinylidene polymers



Vinyl groups can polymerize
Polymerization
In polymer chemistry, polymerization is a process of reacting monomer molecules together in a chemical reaction to form three-dimensional networks or polymer chains...

, forming vinyl polymer
Vinyl polymer
Vinyl polymers are a group of polymers derived from vinyl monomers. Their backbone is an extended alkane chain, made by polymerizing an alkene group into a chain . In popular usage, "vinyl" refers only to polyvinyl chloride...

s. In these polymers, the double bonds of the vinyl monomer
Monomer
A monomer is an atom or a small molecule that may bind chemically to other monomers to form a polymer; the term "monomeric protein" may also be used to describe one of the proteins making up a multiprotein complex...

s turn into single bonds and the different monomers are joined by single bonds. Vinyl groups do not exist in vinyl polymer; the term refers to the precursor. It is sometimes 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. The following table gives some examples of vinyl and vinylidene polymers.
Monomer type Monomer example Example of resulting polymer
Vinyl Vinyl chloride
Vinyl chloride
Vinyl chloride is the 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 . At ambient pressure and temperature, vinyl chloride...

 
Polyvinyl chloride
Polyvinyl chloride
Polyvinyl chloride, commonly abbreviated PVC, is a thermoplastic polymer. It is a vinyl polymer constructed of repeating vinyl groups having one hydrogen replaced by chloride. Polyvinyl chloride is the third most widely produced plastic, after polyethylene and polypropylene. PVC is widely used in...

 (PVC)
Vinyl fluoride
Vinyl fluoride
Vinyl fluoride is an organic halide with the chemical formula C2H3F. It is a colorless gas with a faint etherlike odor. It is used as the monomeric precursor to the fluoropolymer polyvinylfluoride.-Production:...

 
Polyvinyl fluoride
Polyvinyl fluoride
Polyvinyl fluoride or ā€“nā€“ is a polymer material mainly used in flammability-lowering coating of airplane interiors and photovoltaic module backsheets. It is also used in raincoats and metal sheeting...

 (PVF)
Vinyl acetate
Vinyl acetate
Vinyl acetate is an organic compound with the formula CH3COOCH=CH2. A colorless liquid with a pungent odor, it is the precursor to polyvinyl acetate, an important polymer in industry.-Production:...

 
Polyvinyl acetate
Polyvinyl acetate
Polyvinyl acetate, PVA, PVAc, poly, is a rubbery synthetic polymer with the formula n. It belongs to the polyvinyl esters family with the general formula -[RCOOCHCH2]-...

 (PVAc)
Vinylidene Vinylidene chloride  Polyvinylidene chloride
Polyvinylidene chloride
Polyvinylidene chloride is a polymer derived from vinylidene chloride.-History:Ralph Wiley, a Dow Chemical lab worker, accidentally discovered polyvinylidene chloride in 1933. While cleaning laboratory glassware, he came across a vial he could not scrub clean...

 (PVDC)
Vinylidene fluoride Polyvinylidene fluoride
Polyvinylidene fluoride
Polyvinylidene fluoride, or PVDF is a highly non-reactive and pure thermoplastic fluoropolymer.PVDF is a specialty plastic material in the fluoropolymer family; it is used generally in applications requiring the highest purity, strength, and resistance to solvents, acids, bases and heat and low...

 (PVDF)

Reactivity


Vinyl groups are alkene
Alkene
In organic chemistry, an alkene, olefin, or olefine is an unsaturated chemical compound containing at least one carbon-to-carbon double bond...

s. If activated by an adjacent group, the increased polarization of the bond gives rise to characteristic reactivity, which is termed vinylogous
Vinylogous
Vinylogous is an adjective used to apply the concept of vinylogy taught in intermediate undergraduate through graduate/research organic chemistry. Vinylogy has been defined as the transmission of electronic effects through a conjugated organic bonding system...

:
  • In allyl
    Allyl
    An allyl group is a substituent with the structural formula H2C=CH-CH2R, where R is the connection to the rest of the molecule. It is made up of a methylene , attached to a vinyl group . The name is derived from the Latin word for garlic, Allium sativum. Theodor Wertheim isolated an allyl...

     compounds, where the next carbon is saturated but substituted once, allylic rearrangement
    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....

     and related reactions are observed.
    • Allyl Grignard reagents can attack with the vinyl end first.
  • If next to an electron-withdrawing group, conjugate addition (Michael addition) occurs.


Vinyl organometallics, e.g. vinyl lithium, participate in coupling reactions such as in Negishi coupling
Negishi coupling
The Negishi coupling is a cross coupling reaction in organic chemistry involving an organozinc compound, an organic halide and a nickel or palladium catalyst creating a new carbon-carbon covalent bond:* The halide X can be chloride, bromine or iodine but also a triflate or acetyloxy group with as...

.

See also

  • Acetylenic
    Acetylenic
    In organic chemistry, the term acetylenic designates*A doubly unsaturated position on a molecular framework, for instance in an alkyne such as acetylene;*An ethynyl fragment, HC\equivC-, or substituted homologue.- See also :...

  • Allylic/Homoallylic
  • Benzylic
  • Propargylic/Homopropargylic
  • Vinylogous
    Vinylogous
    Vinylogous is an adjective used to apply the concept of vinylogy taught in intermediate undergraduate through graduate/research organic chemistry. Vinylogy has been defined as the transmission of electronic effects through a conjugated organic bonding system...