Vinyl alcohol, also called ethenol (IUPAC name), is an 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....

. It is not to be confused with the drinking alcohol, ethanol

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...

. With the formula

Chemical formula

A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....

 ₂CHH, vinyl alcohol is an isomer of acetaldehyde

Acetaldehyde

Acetaldehyde is an organic chemical compound with the formula CH3CHO or MeCHO. It is one of the most important aldehydes, occurring widely in nature and being produced on a large scale industrially. Acetaldehyde occurs naturally in coffee, bread, and ripe fruit, and is produced by plants as part...

 and ethylene oxide

Ethylene oxide

Ethylene oxide, also called oxirane, is the organic compound with the formula . It is a cyclic ether. This means that it is composed of two alkyl groups attached to an oxygen atom in a cyclic shape . This colorless flammable gas with a faintly sweet odor is the simplest epoxide, a three-membered...

. Under normal conditions, it converts (tautomer

Tautomer

Tautomers are isomers of organic compounds that readily interconvert by a chemical reaction called tautomerization. This reaction commonly results in the formal migration of a hydrogen atom or proton, accompanied by a switch of a single bond and adjacent double bond...

izes) to acetaldehyde:

Relationship to polyvinylalcohol

Because of the instability of vinyl alcohol, the thermoplastic

Thermoplastic

Thermoplastic, also known as a thermosoftening plastic, is a polymer that turns to a liquid when heated and freezes to a very glassy state when cooled sufficiently...

 polyvinyl alcohol

Polyvinyl alcohol

Polyvinyl alcohol is a water-soluble synthetic polymer .-Properties:...

 (PVA or PVOH) is made indirectly by polymerization of 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:...

 followed by hydrolysis

Hydrolysis

Hydrolysis is a chemical reaction during which molecules of water are split into hydrogen cations and hydroxide anions in the process of a chemical mechanism. It is the type of reaction that is used to break down certain polymers, especially those made by condensation polymerization...

 of the ester

Ester

Esters are chemical compounds derived by reacting an oxoacid with a hydroxyl compound such as an alcohol or phenol. Esters are usually derived from an inorganic acid or organic acid in which at least one -OH group is replaced by an -O-alkyl group, and most commonly from carboxylic acids and...

 bonds (Ac = acetyl, HOAc = acetic acid):

n CH₂=CHOAc → (CH₂-CHOAc)_n

(CH₂-CHOAc)_n + n H₂O → (CH₂-CHOH)_n + n HOAc

As a ligand

Several metal complexes are known that contain vinyl alcohol as a ligand

Ligand

In coordination chemistry, a ligand is an ion or molecule that binds to a central metal atom to form a coordination complex. The bonding between metal and ligand generally involves formal donation of one or more of the ligand's electron pairs. The nature of metal-ligand bonding can range from...

. One example is Pt(acac)(η²-C₂H₃OH)Cl.

Occurrence in interstellar medium

Vinyl alcohol was discovered in the molecular cloud

Molecular cloud

A molecular cloud, sometimes called a stellar nursery if star formation is occurring within, is a type of interstellar cloud whose density and size permits the formation of molecules, most commonly molecular hydrogen ....

 Sagittarius B using the 12-meter radio telescope

Radio telescope

A radio telescope is a form of directional radio antenna used in radio astronomy. The same types of antennas are also used in tracking and collecting data from satellites and space probes...

 at the Kitt Peak National Observatory

Kitt Peak National Observatory

The Kitt Peak National Observatory is a United States astronomical observatory located on 2,096 m Kitt Peak of the Quinlan Mountains in the Arizona-Sonoran Desert on the Tohono O'odham Nation, southwest of Tucson...

. This vinyl alcohol being stable in the (dilute) interstellar medium

Interstellar medium

In astronomy, the interstellar medium is the matter that exists in the space between the star systems in a galaxy. This matter includes gas in ionic, atomic, and molecular form, dust, and cosmic rays. It fills interstellar space and blends smoothly into the surrounding intergalactic space...

 shows that its tautomerization is not unimolecular

Molecularity

Molecularity in chemistry is the number of colliding molecular entities that are involved in a single reaction step. While the order of a reaction is derived experimentally, the molecularity is a theoretical concept and can only be applied to elementary reactions...

.