Alkynes
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Alkynes
\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 118 picometers (for C2H2) is much shorter than the C=C distance in alkenes (132 pm, for C2H4) or the C–C bond in alkanes (153 pm). : The triple bond is very strong with a bond strength of 839 kJ/mol. Th ...
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Alkyne General Formulae V
\ce \ce Acetylene \ce \ce \ce Propyne \ce \ce \ce \ce 1-Butyne In organic chemistry, an alkyne is an Saturated and unsaturated compounds, unsaturated hydrocarbon containing at least one carbon—carbon triple bond. The simplest Open-chain compound, 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 of organic chemistry, 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 118 picometers (for C2H2) is much shorter than the C=C distance in alkenes (132 pm, for C2H4) or the C–C bond in alka ...
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Acetylene
Acetylene (Chemical nomenclature, systematic name: ethyne) is a chemical compound with the formula and structure . It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is unstable in its pure form and thus is usually handled as a solution. Pure acetylene is odorless, but commercial grades usually have a marked odor due to impurities such as divinyl sulfide and phosphine.Compressed Gas Association (1995Material Safety and Data Sheet – Acetylene As an alkyne, acetylene is Saturated and unsaturated compounds, unsaturated because its two carbon atoms are Chemical bond, bonded together in a triple bond. The carbon–carbon triple bond places all four atoms in the same straight line, with CCH bond angles of 180°. The triple bond in acetylene results in a high energy content that is released when acetylene is burned. Discovery Acetylene was discovered in 1836 by Edmund Davy, who identified it as a "new carburet ...
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Ethyne
Acetylene (systematic name: ethyne) is a chemical compound with the formula and structure . It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is unstable in its pure form and thus is usually handled as a solution. Pure acetylene is odorless, but commercial grades usually have a marked odor due to impurities such as divinyl sulfide and phosphine.Compressed Gas Association (1995Material Safety and Data Sheet – Acetylene As an alkyne, acetylene is unsaturated because its two carbon atoms are bonded together in a triple bond. The carbon–carbon triple bond places all four atoms in the same straight line, with CCH bond angles of 180°. The triple bond in acetylene results in a high energy content that is released when acetylene is burned. Discovery Acetylene was discovered in 1836 by Edmund Davy, who identified it as a "new carburet of hydrogen". It was an accidental discovery while attempting to isolate ...
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Propyne
Propyne (methylacetylene) is an alkyne with the chemical formula . It is a component of MAPD gas—along with its isomer propadiene (allene), which was commonly used in gas welding. Unlike acetylene, propyne can be safely condensed.Peter Pässler, Werner Hefner, Klaus Buckl, Helmut Meinass, Andreas Meiswinkel, Hans-Jürgen Wernicke, Günter Ebersberg, Richard Müller, Jürgen Bässler, Hartmut Behringer, Dieter Mayer, "Acetylene" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim 2007 (). Production and equilibrium with propadiene Propyne exists in equilibrium with propadiene, the mixture of propyne and propadiene being called MAPD: : The coefficient of equilibrium ''K''eq is 0.22 at 270 °C or 0.1 at 5 °C. MAPD is produced as a side product, often an undesirable one, by cracking propane to produce propene, an important feedstock in the chemical industry. MAPD interferes with the catalytic polymerization of propene. Laboratory methods Propyn ...
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IUPAC Nomenclature Of Organic Chemistry
In chemical nomenclature, the IUPAC nomenclature of organic chemistry is a method of naming organic chemical compounds as recommended by the International Union of Pure and Applied Chemistry (IUPAC). It is published in the '' Nomenclature of Organic Chemistry'' (informally called thBlue Book. Ideally, every possible organic compound should have a name from which an unambiguous structural formula can be created. There is also an IUPAC nomenclature of inorganic chemistry. To avoid long and tedious names in normal communication, the official IUPAC naming recommendations are not always followed in practice, except when it is necessary to give an unambiguous and absolute definition to a compound. IUPAC names can sometimes be simpler than older names, as with ethanol, instead of ethyl alcohol. For relatively simple molecules they can be more easily understood than non-systematic names, which must be learnt or looked over. However, the common or trivial name is often substantially ...
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Methylacetylene
Propyne (methylacetylene) is an alkyne with the chemical formula . It is a component of MAPD gas—along with its isomer propadiene (allene), which was commonly used in gas welding. Unlike acetylene, propyne can be safely condensed.Peter Pässler, Werner Hefner, Klaus Buckl, Helmut Meinass, Andreas Meiswinkel, Hans-Jürgen Wernicke, Günter Ebersberg, Richard Müller, Jürgen Bässler, Hartmut Behringer, Dieter Mayer, "Acetylene" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim 2007 (). Production and equilibrium with propadiene Propyne exists in equilibrium with propadiene, the mixture of propyne and propadiene being called MAPD: : The coefficient of equilibrium ''K''eq is 0.22 at 270 °C or 0.1 at 5 °C. MAPD is produced as a side product, often an undesirable one, by cracking propane to produce propene, an important feedstock in the chemical industry. MAPD interferes with the catalytic polymerization of propene. Laboratory methods Propyne ...
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1-Butyne
1-Butyne is an organic compound with the formula . It is a terminal alkyne. The compound is a common terminal alkyne substrate in diverse studies of catalysis. It is a colorless combustible gas. In 2017, was produced in the USA. 1-Butyne participates in reactions typical for terminal alkynes, such as alkyne metathesis, hydrogenation, condensation with formaldehyde. Based on its heat of combustion, it is slightly more stable than its isomer 2-butyne. The combustion of 1-Butyne produces propargyl radicals, a pre-cursor to soot and polycyclic aromatic hydrocarbons, as the propargyl radicals can form basic aromatic rings, making butyne's fuel usage a concern for emissions. 1-Butyne is in unsaturated C4 petroleum cuts, and has to be separated out in industrial hydrorefining to make 1-butene, which is used to make low density polyethylene and polybutene. Distillation is impractical due to similar boiling points, so 1-butyne is removed by catalytic hydrogenation. Usually the cata ...
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Bond Strength
In chemistry, bond energy (''BE'') is one measure of the strength of a chemical bond. It is sometimes called the mean bond, bond enthalpy, average bond enthalpy, or bond strength. IUPAC defines bond energy as the average value of the gas-phase bond-dissociation energy (usually at a temperature of 298.15 K) for all bonds of the same type within the same chemical species. The bond dissociation energy (enthalpy) is also referred to as bond disruption energy, bond energy, bond strength, or binding energy (abbreviation: ''BDE'', ''BE'', or ''D''). It is defined as the standard enthalpy change of the following fission: R—''X'' → R + ''X''. The ''BDE'', denoted by Dº(R—''X''), is usually derived by the thermochemical equation, : \begin \mathrmX) \ = \Delta H^\circ_f\mathrm + \Delta H^\circ_f(X) - \Delta H^\circ_f(\mathrmX) \end This equation tells us that the ''BDE'' for a given bond is equal to the energy of the individual components that make up the bond when they are free a ...
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Diphenylacetylene
Diphenylacetylene is the chemical compound C6H5C≡CC6H5. The molecule consists of two phenyl groups attached to a C2 unit. A colorless solid, it is used as a building block in organic synthesis and as a Transition metal alkyne complex, ligand in organometallic chemistry. Preparation and structure In one preparation for this compound, benzil is condensed with hydrazine to give the bis(hydrazone), which is oxidized with mercury(II) oxide. Alternatively stilbene is brominated, and the resulting dibromodiphenylethane is subjected to dehydrohalogenation. Yet another method involves the coupling of iodobenzene and the copper salt of phenylacetylene in the Castro-Stephens coupling. The related Sonogashira coupling involves the coupling of iodobenzene and phenylacetylene. Diphenylacetylene is a planar molecule. The central C≡C distance is 119.8 picometers. Derivatives 1,2,3,4-Tetraphenylbutadiene is prepared by reductive coupling of diphenylacetylene using lithium metal followed by h ...
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Orbital Hybridisation
In chemistry, orbital hybridisation (or hybridization) is the concept of mixing atomic orbitals to form new ''hybrid orbitals'' (with different energies, shapes, etc., than the component atomic orbitals) suitable for the pairing of electrons to form chemical bonds in valence bond theory. For example, in a carbon atom which forms four single bonds, the valence-shell s orbital combines with three valence-shell p orbitals to form four equivalent sp3 mixtures in a tetrahedral arrangement around the carbon to bond to four different atoms. Hybrid orbitals are useful in the explanation of molecular geometry and atomic bonding properties and are symmetrically disposed in space. Usually hybrid orbitals are formed by mixing atomic orbitals of comparable energies. History and uses Chemist Linus Pauling first developed the hybridisation theory in 1931 to explain the structure of simple molecules such as methane (CH4) using atomic orbitals. Pauling pointed out that a carbon atom forms four ...
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