In chemistry, an ynol is an alkyne

Alkyne

Alkynes are hydrocarbons that have a triple bond between two carbon atoms, with the 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...

 with a hydroxyl group affixed to one of the two carbons composing the triple bond. The deprotonated anions of ynols are known as ynolates. An ynol with hydroxyl groups on both sides of its triple bond is known as an ynediol; only one ynediol, acetylenediol

Acetylenediol

Acetylenediol, or ethynediol, is a chemical substance with formula HO-C≡C-OH. It is the diol of acetylene. Acetylenediol is unstable in the condensed phase, although its tautomer glyoxal H2H is well known.-Detection:...

, can exist.

Ynolates

Ynolates are chemical compounds with a negatively charged oxygen attached to an alkyne

Alkyne

Alkynes are hydrocarbons that have a triple bond between two carbon atoms, with the 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...

 functionality. They were first synthesized in 1975 by Schöllkopf and Hoppe via the n-butyllithium

N-Butyllithium

n-Butyllithium is an organolithium reagent. It is widely used as a polymerization initiator in the production of elastomers such as polybutadiene or styrene-butadiene-styrene...

 fragmentation of 3,4-diphenylisoxazole.

Synthetically, they behave as ketene

Ketene

A ketene is an organic compound of the form R'RC=C=O. The term is also used specifically to mean ethenone, the simplest ketene, where R' and R are hydrogen atoms.Ketenes were first studied as a class by Hermann Staudinger.-Formation:...

 precursors or synthon

Synthon

A synthon is a concept in retrosynthetic analysis. It is defined as a structural unit within a molecule which is related to a possible synthetic operation. The term was coined by E.J. Corey...

s.

Ynol-ketene tautomerism

Ynols can interconvert with ketene

Ketene

A ketene is an organic compound of the form R'RC=C=O. The term is also used specifically to mean ethenone, the simplest ketene, where R' and R are hydrogen atoms.Ketenes were first studied as a class by Hermann Staudinger.-Formation:...

s. The ynol form is usually unstable, does not survive long, and changes into the ketene. This is because oxygen

Oxygen

Oxygen is the element with atomic number 8 and represented by the symbol O. Its name derives from the Greek roots ὀξύς and -γενής , because at the time of naming, it was mistakenly thought that all acids required oxygen in their composition...

 is more electronegative

Electronegativity

Electronegativity, symbol χ , is a chemical property that describes the tendency of an atom or a functional group to attract electrons towards itself. An atom's electronegativity is affected by both its atomic number and the distance that its valence electrons reside from the charged nucleus...

 than carbon

Carbon

Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...

 and thus forms stronger

Bond energy

In chemistry, bond energy is the measure of bond strength in a chemical bond. It is the heat required to break one Mole of molecules into their individual atoms. For example, the carbon-hydrogen bond energy in methane E is the enthalpy change involved with breaking up one molecule of methane into...

 bonds

Covalent bond

A covalent bond is a form of chemical bonding that is characterized by the sharing of pairs of electrons between atoms. The stable balance of attractive and repulsive forces between atoms when they share electrons is known as covalent bonding....

. For instance, ethynol

Ethynol

Ethynol is an alcohol with the formula C2H2O. It is the much less stable tautomer of ethenone.At low temperature in a solid argon matrix it is possible to isomerize ethenone to form ethynol....

 quickly interconverts with ethenone

Ethenone

Ethenone is the formal name for ketene, an organic compound with formula C2H2O or H2C=C=O. It is the simplest member of the ketene class. It is a tautomer of ethynol.- Properties :...

:

Ynol-ketene isomerism
Ethynol Ethynol Ethynol is an alcohol with the formula C2H2O. It is the much less stable tautomer of ethenone.At low temperature in a solid argon matrix it is possible to isomerize ethenone to form ethynol....	Ethenone Ethenone Ethenone is the formal name for ketene, an organic compound with formula C2H2O or H2C=C=O. It is the simplest member of the ketene class. It is a tautomer of ethynol.- Properties :...