Ethynol
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Ethynol
Ethynol (or hydroxyacetylene) is an alkyne–alcohol (ynol) 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 tautomerise ethenone to form ethynol. See also *Ethanol (ethyl alcohol) *Ethenol (vinyl alcohol) *Acetylenediol Acetylenediol, or ethynediol, is a chemical substance with formula HO−C≡C−OH (an ynol). It is the diol of acetylene. Acetylenediol is unstable in the condensed phase, although its tautomer glyoxal (CHO)2 is well known. Detection Acetyl ... References Alkynols {{Alcohol-stub ...
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Ynol
In organic chemistry, an alkynol (shortened to ynol) is an alkyne with a hydroxyl group affixed to one of the two carbon atoms 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, exists. Ynolates Ynolates are chemical compounds with a negatively charged oxygen atom attached to an alkyne functionality. They were first synthesized in 1975 by Schöllkopf and Hoppe via the ''n''-butyllithium fragmentation of 3,4-diphenylisoxazole. Synthetically, they behave as ketene precursors or synthons. Ynol–ketene tautomerism Ynols can interconvert with ketenes, much like enols can with aldehydes and ketones. The ynol tautomer is usually unstable, does not survive long, and changes into the ketene. This is because oxygen is more electronegative than carbon and thus forms stronger bonds. For instance, ethynol quickly inter ...
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Ethanol
Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an Alcohol (chemistry), alcohol with the chemical formula . Its formula can be also written as or (an ethyl group linked to a hydroxyl group). Ethanol is a Volatility (chemistry), volatile, Combustibility and flammability, flammable, colorless liquid with a characteristic wine-like odor and pungent taste. It is a psychoactive recreational drug, the active ingredient in alcoholic drinks. Ethanol is naturally produced by the fermentation process of Carbohydrate, sugars by yeasts or via Petrochemistry, petrochemical processes such as ethylene hydration. It has medical applications as an antiseptic and disinfectant. It is used as a chemical solvent and in the Chemical synthesis, synthesis of organic compounds, and as a Alcohol fuel, fuel source. Ethanol also can be dehydrated to make ethylene, an important chemical feedstock. As of 2006, world produ ...
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Acetylenediol
Acetylenediol, or ethynediol, is a chemical substance with formula HO−C≡C−OH (an ynol). It is the diol of acetylene. Acetylenediol is unstable in the condensed phase, although its tautomer glyoxal (CHO)2 is well known. Detection Acetylenediol was first observed in the gas-phase by mass spectrometry. The compound was later obtained by photolysis of squaric acid in a solid argon matrix at . Derivatives Alkoxide derivatives Like the diol, most simple ether derivatives are labile. Di-tert-butoxyacetylene is however a distillable liquid. Acetylenediolate salts Salts of the acetylenediolate (ethynediolate) dianion −O−C≡C−O− are known. They are not however prepared from ethynediol, but by the reduction of carbon monoxide. Potassium acetylenediolate (K2C2O2) was first obtained by Liebig in 1834, from the reaction of carbon monoxide with metallic potassium;Justus Liebig (1834), Annalen der Chemie und Pharmacie, volume 11, p. 182. Cited by Raymond N. Vrtis et a ...
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Propargyl Alcohol
Propargyl alcohol, or 2-propyn-1-ol, is an organic compound with the chemical formula, formula C3H4O. It is the simplest stable Alcohol (chemistry), alcohol containing an alkyne functional group. Propargyl alcohol is a colorless viscous liquid that is miscible with water and most polar organic solvents. Reactions and applications Propargyl alcohol polymerizes with heating or treatment with base (chemistry), base. It is used as a corrosion inhibitor, a metal complex solution, a solvent stabilizer and an electroplating brightener additive. It is also used as an intermediate in organic synthesis. Secondary alcohol, Secondary and Tertiary alcohol, tertiary substituted propargylic alcohols undergo catalyzed rearrangement reactions to form carbonyl#α,β-Unsaturated carbonyl compounds, α,β-unsaturated carbonyl compounds via the Meyer–Schuster rearrangement and others. It can be oxidized to propynal or propargylic acid. As an indication of the electronegativity of an Orbital hybri ...
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Alkyne
\ce \ce Acetylene \ce \ce \ce Propyne \ce \ce \ce \ce 1-Butyne In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond. The simplest acyclic alkynes with only one triple bond and no other functional groups form a homologous series with the general chemical formula . Alkynes are traditionally known as acetylenes, although the name ''acetylene'' also refers specifically to , known formally as ethyne using IUPAC nomenclature. Like other hydrocarbons, alkynes are generally hydrophobic. Structure and bonding In acetylene, the H–C≡C bond angles are 180°. By virtue of this bond angle, alkynes are rod-like. Correspondingly, cyclic alkynes are rare. Benzyne cannot be isolated. The C≡C bond distance of 121 picometers is much shorter than the C=C distance in alkenes (134 pm) or the C–C bond in alkanes (153 pm). : The triple bond is very strong with a bond strength of 839 kJ/mol. The sigma bond contribute ...
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Alcohol (chemistry)
In chemistry, an alcohol is a type of organic compound that carries at least one hydroxyl () functional group bound to a saturated carbon atom. The term ''alcohol'' originally referred to the primary alcohol ethanol (ethyl alcohol), which is used as a drug and is the main alcohol present in alcoholic drinks. An important class of alcohols, of which methanol and ethanol are the simplest examples, includes all compounds which conform to the general formula . Simple monoalcohols that are the subject of this article include primary (), secondary () and tertiary () alcohols. The suffix ''-ol'' appears in the IUPAC chemical name of all substances where the hydroxyl group is the functional group with the highest priority. When a higher priority group is present in the compound, the prefix ''hydroxy-'' is used in its IUPAC name. The suffix ''-ol'' in non-IUPAC names (such as paracetamol or cholesterol) also typically indicates that the substance is an alcohol. However, some compou ...
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Chemical Formula
In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, such as parentheses, dashes, brackets, commas and ''plus'' (+) and ''minus'' (−) signs. These are limited to a single typographic line of symbols, which may include Subscript and superscript, subscripts and superscripts. A chemical formula is not a chemical nomenclature, chemical name, and it contains no words. Although a chemical formula may imply certain simple chemical structures, it is not the same as a full chemical structural formula. Chemical formulae can fully specify the structure of only the simplest of molecules and chemical substances, and are generally more limited in power than chemical names and structural formulae. The simplest types of chemical formulae are called ''empirical formulae'', which use letters and numbers ind ...
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Tautomer
Tautomers () are structural isomers (constitutional isomers) of chemical compounds that readily interconvert. The chemical reaction interconverting the two is called tautomerization. This conversion commonly results from the relocation of a hydrogen atom within the compound. The phenomenon of tautomerization is called tautomerism, also called desmotropism. Tautomerism is for example relevant to the behavior of amino acids and nucleic acids, two of the fundamental building blocks of life. Care should be taken not to confuse tautomers with depictions of "contributing structures" in chemical resonance. Tautomers are distinct chemical species that can be distinguished by their differing atomic connectivities, molecular geometries, and physicochemical and spectroscopic properties, whereas resonance forms are merely alternative Lewis structure (valence bond theory) depictions of a single chemical species, whose true structure is best described as the "average" of the idealized, hypothe ...
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Ethenone
In organic chemistry, ethenone is the formal name for ketene, an organic compound with formula or . It is the simplest member of the ketene class. It is an important reagent for acetylations. Properties Ethenone is a highly reactive gas (at standard conditions) and has a sharp irritating odour. It is only reasonably stable at low temperatures (−80 °C). It must therefore always be prepared for each use and processed immediately, otherwise a dimerization to diketene occurs or it reacts to polymers that are difficult to handle. The polymer content formed during the preparation is reduced, for example, by adding sulfur dioxide to the ketene gas. Because of its cumulative double bonds, ethenone is highly reactive and reacts in an addition reaction H-acidic compounds to the corresponding acetic acid derivatives. It does for example react with water to acetic acid or with primary or secondary amines to the corresponding acetamides. Preparation In industrial chemistry, k ...
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Matrix Isolation
Matrix isolation is an experimental technique used in chemistry and physics. It generally involves a material being trapped within an unreactive matrix. A ''host'' matrix is a continuous solid phase in which ''guest'' particles (atoms, molecules, ions, etc.) are embedded. The guest is said to be ''isolated'' within the ''host'' matrix. Initially the term matrix-isolation was used to describe the placing of a chemical species in any unreactive material, often polymers or resins, but more recently has referred specifically to gases in low-temperature solids. A typical matrix isolation experiment involves a guest sample being diluted in the gas phase with the host material, usually a noble gas or nitrogen. This mixture is then deposited on a window that is cooled to below the melting point of the host gas. The sample may then be studied using various spectroscopic procedures. Experimental setup The transparent window, on to which the sample is deposited, is usually cooled using a c ...
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Vinyl Alcohol
Vinyl alcohol, also called ethenol (IUPAC name; not ethanol), is the simplest enol. With the formula , it is a labile compound that converts to acetaldehyde. It is not a precursor to polyvinyl alcohol. Synthesis Vinyl alcohol can be formed by the pyrolytic elimination of water from ethylene glycol at a temperature of 900 °C and low pressure. Tautomerization of vinyl alcohol to acetaldehyde Under normal conditions, vinyl alcohol converts (tautomerizes) to acetaldehyde: : At room temperature, acetaldehyde () is more stable than vinyl alcohol () by 42.7 kJ/mol: : Δ''H''298,g = −42.7 kJ/mol 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 ...
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