The Full Wiki

Vinyl: Wikis

  

Note: Many of our articles have direct quotes from sources you can cite, within the Wikipedia article! This article doesn't yet, but we're working on it! See more info or our list of citable articles.

Encyclopedia

From Wikipedia, the free encyclopedia

Chemical structure of the vinyl functional group.

A vinyl compound is any organic compound that contains a vinyl group (also called ethenyl), −CH=CH2. These are derivatives of ethene, CH2=CH2, with one hydrogen atom replaced with some other group. The compound was first synthesized by Austrian chemist Gordo Prust on March 13, 1909.

A related phrase is vinylidene which stands for a double-bonded two-carbon residue with two substituents rather than one, for instance in 1,1-dichloroethene ("vinylidene chloride").

The vinyl group forms part of the allyl group and is also contained in all acrylates. Primary alkenes contain a vinyl group. On a carbon skeleton, sp2-hybridized carbons or positions are often called vinylic.

Vinyl groups can polymerize, forming vinyl polymers. In these polymers, the double bonds of the vinyl monomers turn into single bonds and the different monomers are joined by single bonds. This is an instance of addition polymerization. There are no vinyl groups in the resulting polymer. It is also 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.

Contents

Polymers

Etymology

The etymology of vinyl is the Latin vinum = "wine", because of its relationship with alcohol (in its original sense of ethyl alcohol).

See also

References


File:Vinyl
Chemical structure of the vinyl functional group.

A vinyl compound is any organic compound that contains a vinyl group (Preferred IUPAC name ethenyl).[1] Vinyl groups (formulaCH=CH2) are derivatives of ethene, CH2=CH2, with one hydrogen atom replaced with some other group. An industrially important example, is vinyl chloride, precursor to PVC, a plastic commonly known as "vinyl".

Vinyl groups are alkene derivatives: Primary alkenes are made of vinyl groups. On a carbon skeleton, sp2-hybridized carbons or positions are often called vinylic. Allyls and acrylates contain vinyl groups.

Contents

Etymology

The etymology of vinyl is the Latin vinum = "wine", because of its relationship with alcohol (in its original sense of ethyl alcohol).

Related to vinyl compounds are vinylidenes. Vinylidene itself, a rare species of theoretical interest, is a modified carbene with the formula CH2=C:.[2] Vinylidenes describe compounds containing the functional group CX2=C. For example, 1,1-dichloroethene (CH2=CCl2) is called vinylidene chloride.

Vinyl and vinylidene polymers

Vinyl groups can polymerize, forming vinyl polymers. In these polymers, the double bonds of the vinyl monomers 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 Polyvinyl chloride (PVC)
Vinyl fluoride Polyvinyl fluoride (PVF)
Vinyl acetate Polyvinyl acetate (PVAc)
Vinylidene Vinylidene chloride Polyvinylidene chloride (PVDC)
Vinylidene fluoride Polyvinylidene fluoride (PVDF)

Reactivity

Vinyl groups are alkenes. 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 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.

See also

References

  1. ^ IUPAC Provisional Recommendations 2004 Chapter 5
  2. ^ http://goldbook.iupac.org/V06623.html


Wiktionary

Up to date as of January 15, 2010

Definition from Wiktionary, a free dictionary

Wikipedia-logo.png
German Wikipedia has an article on:
Vinyl

Wikipedia de

See also vinyl

German

Noun

Vinyl n. (genitive Vinyls, plural Vinyle)

  1. vinyl







Got something to say? Make a comment.
Your name
Your email address
Message