Vinyl alcohol

Not to be confused with ethanol or ethynol.

Vinyl alcohol  | Structural formula of ethenol | Ball-and-stick model of ethenol

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Names
Preferred IUPAC name

Ethenol

Other names

Hydroxyethene
Hydroxyethylene
Ethylenol

Identifiers

CAS Number

* 557-75-5 Y

3D model (JSmol)

* Interactive image

ChEMBL |

* ChEMBL76101 Y

ChemSpider |

* 10726 Y

PubChem CID

* 11199

UNII |

* GO1N1ZPR3B Y

InChI

* InChI=1S/C2H4O/c1-2-3/h2-3H,1H2 Y

Key: IMROMDMJAWUWLK-UHFFFAOYSA-N Y

* InChI=1S/C2H4O/c1-2-3/h2-3H,1H2

* InChI=1S/C2H4O/c1-2-3/h2-3H,1H2

Key: IMROMDMJAWUWLK-UHFFFAOYSA-N

SMILES

* OC=C

Properties

Chemical formula

| C2H4O
Molar mass | 44.053 g/mol
Related compounds

Related compounds

| Allyl alcohol

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Y verify (what is YN ?)
Infobox references

Tracking categories (test):

* PairSizeSet

Vinyl alcohol, also called ethenol (IUPAC name; not ethanol) or ethylenol, is the simplest enol. With the formula CH
2CHOH, it is a labile compound that converts to acetaldehyde immediately upon isolation near room temperature.[1] It is not a practical precursor to any compound.

## Contents

* 1 Synthesis
* 2 Tautomerization of vinyl alcohol to acetaldehyde
* 3 Relationship to poly(vinyl alcohol)
* 4 As a ligand
* 5 Occurrence in interstellar medium
* 6 References

## Synthesis

Vinyl alcohol can be formed by the pyrolytic elimination of water from ethylene glycol at a temperature of 900 °C and low pressure. Such processes are of no practical importance.[2]

## Tautomerization of vinyl alcohol to acetaldehyde

Under normal conditions, vinyl alcohol converts (tautomerizes) to acetaldehyde:

250px

At room temperature, acetaldehyde (H
3CC(O)H) is more stable than vinyl alcohol (H
2C=CHOH) by 42.7 kJ/mol.[3] Vinyl alcohol gas isomerizes to the aldehyde with a half-life of 30 min at room temperature.[1]

2C=CHOH → H
3CC(O)H
The industrial synthesis of acetaldehyde (Wacker process) proceeds via the intermediacy of a vinyl alcohol complex.[4]

The uncatalyzed keto–enol tautomerism by a 1,3-hydrogen migration is forbidden by the Woodward–Hoffmann rules and therefore has a high activation barrier and is not a significant pathway at or near room temperature. However, even trace amounts of acids or bases (including water) can catalyze the reaction. Even with rigorous precautions to minimize adventitious moisture or proton sources, vinyl alcohol can only be stored for minutes to hours before it isomerizes to acetaldehyde. (Carbonic acid is another example of a substance that is stable when rigorously pure, but decomposes rapidly due to catalysis by trace moisture.)

The tautomerization can also be catalyzed via photochemical process. These findings suggest that the keto–enol tautomerization is a viable route under atmospheric and stratospheric conditions, relevant to a role for vinyl alcohol in the production of organic acids in the atmosphere.[5][6]

Vinyl alcohol can be stabilized by controlling the water concentration in the system and utilizing the kinetic favorability of the deuterium-produced kinetic isotope effect (kH+/kD+ = 4.75, kH2O/kD2O = 12). Deuterium stabilization can be accomplished through hydrolysis of a ketene precursor in the presence of a slight stoichiometric excess of heavy water (D2O). Studies show that the tautomerization process is significantly inhibited at ambient temperatures ( kt ≈ 10−6 M/s), and the half-life of the enol form can easily be increased to t1/2 = 42 minutes for first-order hydrolysis kinetics.[7]

## Relationship to poly(vinyl alcohol)

Because of the instability of vinyl alcohol, the thermoplastic polyvinyl alcohol (PVA or PVOH) is made indirectly by polymerization of vinyl acetate followed by hydrolysis of the ester bonds (Ac = acetyl; HOAc = acetic acid):[8]

n CH
2=CHOAc → (CH
2–CHOAc)

(CH
2–CHOAc)
n \+ n H
2O → (CH
2–CHOH)
n \+ n HOAc

## As a ligand

Several metal complexes are known that contain vinyl alcohol as a ligand. One example is Pt(acac)(η2-C2H3OH)Cl.[9]

## Occurrence in interstellar medium

Vinyl alcohol was detected in the molecular cloud Sagittarius B in 2001, the last of the three stable isomers of C2H4O (after acetaldehyde and ethylene oxide) to be detected in space.[10][11] Its stability in the (dilute) interstellar medium shows that its tautomerization does not happen unimolecularly,[11] a fact attributed to the size of the activation energy barrier to the rearrangement being insurmountable at temperatures present in interstellar space.[12] The vinyl alcohol to acetaldehyde rearrangement is the only keto-enol tautomerisation to have been detected in deep space, induced by the provision of secondary electrons from galactic cosmic rays.[12]

## References

1. ↑ 1.0 1.1 Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, p. 101, ISBN 978-0-471-72091-1, https://books.google.com/books?id=JDR-nZpojeEC&printsec=frontcover
2. ↑ Clayden, Jonathan; Greeves, Nick; Warren, Stuart (2012). Organic Chemistry (2nd ed.). Oxford University Press. pp. 456–57. ISBN 978-0-19-927029-3.
3. ↑ R.D. Johnson III. "CCCBDB NIST Standard Reference Database.". https://cccbdb.nist.gov/.
4. ↑ Keith, J. A.; Henry, P. M. (2009). "The Mechanism of the Wacker Reaction: A Tale of Two Hydroxypalladations". Angew. Chem. Int. Ed. 48 (48): 9038–9049. doi:10.1002/anie.200902194. PMID 19834921.
5. ↑ Heazlewood, B. R.; Maccarone, A. T.; Andrews, D. U.; Osborn, D. L.; Harding, L. B.; Klippenstein, S. J.; Jordan, M. J. T.; Kable, S. H. (2011). "Near-threshold H/D exchange in CD3CHO photodissociation". Nature Chemistry 3 (6): 443−448. doi:10.1038/nchem.1052. PMID 21602858. Bibcode: 2011NatCh...3..443H.
6. ↑ Andrews, D. U.; Heazlewood, B. R.; Maccarone, A. T.; Conroy, T.; Payne, R. J.; Jordan, M. J. T.; Kable, S. H. (2012). "Photo-tautomerization of acetaldehyde to vinyl alcohol: A potential route to tropospheric acids". Science 337 (6099): 1203–1206. doi:10.1126/science.1220712. PMID 22903524. Bibcode: 2012Sci...337.1203A.
7. ↑ Cederstav, Anna K.; Novak, Bruce M. (1994). "Investigations into the Chemistry of Thermodynamically Unstable Species. The Direct Polymerization of Vinyl Alcohol, the Enolic Tautomer of Acetaldehyde". Journal of the American Chemical Society 100 (9): 4073–4074. doi:10.1021/ja00088a051.
8. ↑ Hallensleben, Manfred L. (2000). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a21_743.
9. ↑ Cotton, F. A.; Francis, J. N.; Frenz, B. A.; Tsutsui, M. (1973). "Structure of a dihapto(vinyl alcohol) complex of platinum(II)". Journal of the American Chemical Society 95 (8): 2483–6. doi:10.1021/ja00789a011.
10. ↑ Blue, Charles (October 1, 2001). "Scientists Toast the Discovery of Vinyl Alcohol in Interstellar Space" (Press release). National Radio Astronomy Observatory. Retrieved December 20, 2006.
11. ↑ 11.0 11.1 Turner, B. E.; Apponi, A. J. (2001). "Microwave Detection of Interstellar Vinyl Alcohol, CH2=CHOH". The Astrophysical Journal 561 (2): L207–L210. doi:10.1086/324762.CH2=CHOH&rft.jtitle=[[Astronomy:The+Astrophysical+Journal|The+Astrophysical+Journal]]&rft.aulast=Turner&rft.aufirst=B.+E.&rft.au=Turner, B.+E.&rft.au=Apponi, A.+J.&rft.date=2001&rft.volume=561&rft.issue=2&rft.pages=L207–L210&rft_id=info:doi/10.1086/324762&rfr_id=info:sid/en.wikibooks.org:Chemistry:Vinyl_alcohol">
12. ↑ 12.0 12.1 Kleimeier, N. Fabian; Kaiser, Ralf I. (2021). "Interstellar Enolization-Acetaldehyde (CH3CHO) and Vinyl Alcohol (H2CCH(OH)) as a Case Study". ChemPhysChem 22 (12): 1229–1236. doi:10.1002/cphc.202100111. PMID 33913232.CH3CHO)+and+Vinyl+Alcohol+(H2CCH(OH))+as+a+Case+Study&rft.jtitle=ChemPhysChem&rft.aulast=Kleimeier&rft.aufirst=N.+Fabian&rft.au=Kleimeier, N.+Fabian&rft.au=Kaiser, Ralf+I.&rft.date=2021&rft.volume=22&rft.issue=12&rft.pages=1229–1236&rft_id=info:doi/10.1002/cphc.202100111&rft_id=info:pmid/33913232&rfr_id=info:sid/en.wikibooks.org:Chemistry:Vinyl_alcohol">

* v
* t
* e

Molecules detected in outer space

Molecules|

| Diatomic|

* Aluminium monochloride
* Aluminium monofluoride
* Aluminium monoxide
* Argonium
* Carbon monophosphide
* Carbon monosulfide
* Carbon monoxide
* Carborundum
* Cyanogen radical
* Diatomic carbon
* Fluoromethylidynium
* Helium hydride ion
* Hydrogen chloride
* Hydrogen fluoride
* Hydrogen (molecular)
* Hydroxyl radical
* Iron(II) oxide
* Magnesium monohydride cation
* Methylidyne radical
* Nitric oxide
* Nitrogen (molecular)
* Nitrogen monohydride
* Nitrogen sulfide
* Oxygen (molecular)
* Phosphorus monoxide
* Phosphorus mononitride
* Potassium chloride
* Silicon carbide
* Silicon mononitride
* Silicon monoxide
* Silicon monosulfide
* Sodium chloride
* Sodium iodide
* Sulfur monohydride
* Sulfur monoxide
* Titanium oxide

|
|

Triatomic|

* Aluminium hydroxide
* Aluminium isocyanide
* Amino radical
* Carbon dioxide
* Carbonyl sulfide
* CCP radical
* Chloronium
* Diazenylium
* Dicarbon monoxide
* Disilicon carbide
* Ethynyl radical
* Formyl radical
* Hydrogen cyanide (HCN)
* Hydrogen isocyanide (HNC)
* Hydrogen sulfide
* Hydroperoxyl
* Iron cyanide
* Isoformyl
* Magnesium cyanide
* Magnesium isocyanide
* Methylene radical
* N2H+
* Nitrous oxide
* Nitroxyl
* Ozone
* Phosphaethyne
* Potassium cyanide
* Protonated molecular hydrogen
* Sodium cyanide
* Sodium hydroxide
* Silicon carbonitride
* c-Silicon dicarbide
* SiNC
* Sulfur dioxide
* Thioformyl
* Thioxoethenylidene
* Titanium dioxide
* Tricarbon
* Water

Four
atoms|

* Acetylene
* Ammonia
* Cyanic acid
* Cyanoethynyl
* Cyclopropynylidyne
* Formaldehyde
* Fulminic acid
* HCCN
* Hydrogen peroxide
* Hydromagnesium isocyanide
* Isocyanic acid
* Isothiocyanic acid
* Ketenyl
* Methylene amidogen
* Methyl radical
* Propynylidyne
* Protonated carbon dioxide
* Protonated hydrogen cyanide
* Silicon tricarbide
* Thioformaldehyde
* Tricarbon monoxide
* Tricarbon sulfide
* Thiocyanic acid

Five
atoms|

* Ammonium ion
* Butadiynyl
* Carbodiimide
* Cyanamide
* Cyanoacetylene
* Cyanoformaldehyde
* Cyanomethyl
* Cyclopropenylidene
* Formic acid
* Isocyanoacetylene
* Ketene
* Methane
* Methoxy radical
* Methylenimine
* Propadienylidene
* Protonated formaldehyde
* Protonated formaldehyde
* Silane
* Silicon-carbide cluster

Six
atoms|

* Acetonitrile
* Cyanobutadiynyl radical
* E-Cyanomethanimine
* Cyclopropenone
* Diacetylene
* Ethylene
* Formamide
* HC4N
* Ketenimine
* Methanethiol
* Methanol
* Methyl isocyanide
* Pentynylidyne
* Propynal
* Protonated cyanoacetylene

Seven
atoms|

* Acetaldehyde
* Acrylonitrile
* Vinyl cyanide
* Cyanodiacetylene
* Ethylene oxide
* Glycolonitrile
* Hexatriynyl radical
* Methylacetylene
* Methylamine
* Methyl isocyanate
* Vinyl alcohol

Eight
atoms|

* Acetic acid
* Aminoacetonitrile
* Cyanoallene
* Ethanimine
* Glycolaldehyde
* Heptatrienyl radical
* Hexapentaenylidene
* Methylcyanoacetylene
* Methyl formate
* Propenal

Nine
atoms|

* Acetamide
* Cyanohexatriyne
* Cyanotriacetylene
* Dimethyl ether
* Ethanol
* Methyldiacetylene
* Octatetraynyl radical
* Propene
* Propionitrile

Ten
atoms
or more|

* Acetone
* Benzene
* Benzonitrile
* Buckminsterfullerene (C60, C60+, fullerene, buckyball)
* C70 fullerene
* Cyanodecapentayne
* Cyanopentaacetylene
* Cyanotetra-acetylene
* Ethylene glycol
* Ethyl formate
* Methyl acetate
* Methyl-cyano-diacetylene
* Methyltriacetylene
* Propanal
* n-Propyl cyanide
* Pyrimidine

Deuterated
molecules|

* Ammonia
* Ammonium ion
* Formaldehyde
* Formyl radical
* Heavy water
* Hydrogen cyanide
* Hydrogen deuteride
* Hydrogen isocyanide
* Methylacetylene
* N2D+
* Trihydrogen cation

Unconfirmed|

* Anthracene
* Dihydroxyacetone
* Ethyl methyl ether
* Glycine
* Graphene
* H2NCO+
* Linear C5
* Naphthalene cation
* Phosphine
* Pyrene
* Silylidine

Related|

* Abiogenesis
* Astrobiology
* Astrochemistry
* Atomic and molecular astrophysics
* Chemical formula
* Circumstellar envelope
* Cosmic dust
* Cosmic ray
* Cosmochemistry
* Diffuse interstellar band
* Earliest known life forms
* Extraterrestrial life
* Extraterrestrial liquid water
* Forbidden mechanism
* Homochirality
* Intergalactic dust
* Interplanetary medium
* Interstellar medium
* Photodissociation region
* Iron–sulfur world theory
* Kerogen
* Molecules in stars
* Nexus for Exoplanet System Science
* Organic compound
* Outer space
* PAH world hypothesis
* Panspermia
* Polycyclic aromatic hydrocarbon (PAH)
* RNA world hypothesis
* Spectroscopy
* Tholin

* Category:Astrochemistry
*   *   *

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* t
* e

Alcohols

Straight-chain
primary
alcohols (1°)|

* Methanol (C1)
* Ethanol (C2)
* 1-Propanol (C3)
* n-Butanol (C4)
* 1-Pentanol (C5)
* 1-Hexanol (C6)
* 1-Heptanol (C7)
* 1-Octanol (C8)
* 1-Nonanol (C9)
* 1-Decanol (C10)
* Undecanol (C11)
* Dodecanol (C12)
* Tridecan-1-ol (C13)
* 1-Tetradecanol (C14)
* 1-Pentadecanol (C15)
* Cetyl alcohol (C16)
* Heptadecan-1-ol (C17)
* Stearyl alcohol (C18)
* Nonadecan-1-ol (C19)
* Arachidyl alcohol (C20)
* Heneicosan-1-ol (C21)
* Docosanol (C22)
* Tricosan-1-ol (C23)
* 1-Tetracosanol (C24)
* Pentacosan-1-ol (C25)
* 1-Hexacosanol (C26)
* 1-Heptacosanol (C27)
* 1-Octacosanol (C28)
* 1-Nonacosanol (C29)
* Triacontanol (C30)
* Hentriacontanol (C31)
* Dotriacontanol (C32)
* Tritriacontanol (C33)
* Tetratriacontanol (C34)
* Pentatriacontanol (C35)
* Hexatriacontanol (C36)
* 1-Heptatriacontanol (C37)
* 1-Octatriacontanol (C38)
* Nonatriacontan-1-ol (C39)
* Tetracontanol (C40)

Other primary
alcohols|

* Isobutanol (C4)
* Isoamyl alcohol (C5)
* 2-Methyl-1-butanol (C5)
* Phenethyl alcohol (C8)
* Tryptophol (C10)

Secondary
alcohols (2°)|

* Isopropanol (C3)
* Cyclopropanol (C3)
* 2-Butanol (C4)
* 2-Pentanol (C5)
* 3-Pentanol (C5)
* Cyclopentanol (C5)
* 2-Hexanol (C6)
* 3-Hexanol (C6)
* Pinacolyl alcohol (C6)
* Cyclohexanol (C6)
* 2-Heptanol (C7)
* 3-Heptanol (C7)
* 2-Octanol (C8)

Tertiary
alcohols (3°)|

* tert-Butyl alcohol (C4)
* tert-Amyl alcohol (C5)
* 2-Methyl-2-pentanol (C6)
* 2-Methylhexan-2-ol (C7)
* 2-Methylheptan-2-ol (C8)
* 3-Methyl-3-pentanol (C6)
* 3-Methyloctan-3-ol (C9)

Preparations|

* Substitution of haloalkane
* Carbonyl reduction
* Ether cleavage
* Hydrolysis of epoxide
* Hydration of alkene
* Ziegler process

Reactions|

* Deprotonation
* Protonation
* Alcohol oxidation
* Glycol cleavage
* Nucleophilic substitution
* Fischer–Speier esterification
* Williamson ether synthesis
* Elimination reaction
* Nucleophilic substitution of carbonyl group
* Friedel-Crafts alkylation
* Nucleophilic conjugate addition
* Transesterification

* Category

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