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4-octyne
4-Octyne, also known as dipropylethyne, is a type of alkyne with a triple bond at its fourth carbon (the '4-' indicates the location of the triple bond in the chain). Its formula is C8H14. 4-Octyne forms with 5-decyne, 3-hexyne, and 2-butyne a group of symmetric alkynes. Preparation One method for synthesizing 4-octyne is the reaction between acetylene and two equivalents of 1-bromopropane. Acetylene is first deprotonated by a base to give an anion, which then undergoes nucleophilic substitution with the bromopropane. The resulting alkyne is again deprotonated and reacts similarly with a second molecule of bromopropane. This reaction can be carried out in liquid ammonia at −70 °C with sodium amide as the base. Another synthetic route is the elimination reaction of 4,5-dibromooctane, which can be done in similar conditions. Properties 4-octyne is a colorless liquid at room temperature. Its density at 25 °C and otherwise stable conditions is 0.751 g/mL. The boiling poi ...
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5-decyne
5-Decyne, also known as dibutylethyne, is a type of alkyne with a triple bond at its fifth carbon (the '5-' indicates the location of the triple bond in the chain). Its formula is C10H18. Its density at 25 °C and otherwise standard conditions is 0.766 g/ml. The boiling point is 177 °C.David R. Lide (Hrsg.): CRC Handbook of Chemistry and Physics. 90. Auflage. (Internet-Version: 2010), CRC Press/Taylor and Francis, Boca Raton, Florida, Physical Constants of Organic Compounds, S. 3-136. The average molar mass is 138.25 g/mol. 5-Decyne forms a group of symmetric alkynes with 4-octyne, 3-hexyne, and 2-butyne. See also * 1-Decyne References {{DEFAULTSORT:Decyne, 5- Alkynes ...
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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 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. ...
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Triple Bond
A triple bond in chemistry is a chemical bond between two atoms involving six Electron pair bond, bonding electrons instead of the usual two in a covalent bond, covalent single bond. Triple bonds are stronger than the equivalent covalent bond, single bonds or double bond, double bonds, with a bond order of three. The most common triple bond is in a nitrogen N2 molecule; the second most common is that between two carbon atoms, which can be found in alkynes. Other functional groups containing a triple bond are cyanides and isocyanides. Some diatomic molecules, such as diphosphorus and carbon monoxide, are also triple bonded. In skeletal formula, skeletal formulae the triple bond is drawn as three parallel lines (≡) between the two connected atoms. Bonding Triple bonding can be explained in terms of orbital hybridization. In the case of acetylene, each carbon atom has two sp orbital, sp-orbitals and two p-orbitals. The two sp-orbitals are linear, with 180° bond angles, and occupy ...
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Carbon
Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 electrons. It belongs to group 14 of the periodic table. Carbon makes up about 0.025 percent of Earth's crust. Three Isotopes of carbon, isotopes occur naturally, carbon-12, C and carbon-13, C being stable, while carbon-14, C is a radionuclide, decaying with a half-life of 5,700 years. Carbon is one of the timeline of chemical element discoveries#Pre-modern and early modern discoveries, few elements known since antiquity. Carbon is the 15th abundance of elements in Earth's crust, most abundant element in the Earth's crust, and the abundance of the chemical elements, fourth most abundant element in the universe by mass after hydrogen, helium, and oxygen. Carbon's abundance, its unique diversity of organic compounds, and its unusual abi ...
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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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1-Bromopropane
1-Bromopropane (also known as ''n''-propyl bromide or nPB) is a bromoalkane with the chemical formula CH3CH2CH2Br. It is a colorless, flammable liquid that is used as a solvent. It has a characteristic hydrocarbon odor. Its industrial applications increased dramatically in the 21st century due to the phasing out of chlorofluorocarbons and chloroalkanes such as 1,1,1-trichloroethane under the Montreal Protocol. It was also used as a dry cleaning solvent as a substitute for perchloroethylene for a short time in the United States. 1-Bromopropane is highly neurotoxic and possibly carcinogenic to humans. Preparation Industrial routes to 1-bromopropane involve free-radical additions to the corresponding alkenes. In this way, the anti-Markovnikov product is obtained.David Ioffe, Arieh Kampf "Bromine, Organic Compounds" in Kirk-Othmer Encyclopedia of Chemical Technology 2002 by John Wiley & Sons. . Alternatively, ''n''propanol may be substitutively brominated. The latter reaction is ...
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Nucleophilic Substitution
In chemistry, a nucleophilic substitution (SN) is a class of chemical reactions in which an electron-rich chemical species (known as a nucleophile) replaces a functional group within another electron-deficient molecule (known as the electrophile). The molecule that contains the electrophile and the leaving functional group is called the substrate. The most general form of the reaction may be given as the following: :\text\mathbf + \ce + \text\mathbf The electron pair (:) from the nucleophile (Nuc) attacks the substrate () and bonds with it. Simultaneously, the leaving group (LG) departs with an electron pair. The principal product in this case is . The nucleophile may be electrically neutral or negatively charged, whereas the substrate is typically neutral or positively charged. An example of nucleophilic substitution is the hydrolysis of an alkyl bromide, R-Br under basic conditions, where the attacking nucleophile is hydroxyl () and the leaving group is bromide (). :O ...
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Ammonia
Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the chemical formula, formula . A Binary compounds of hydrogen, stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pungent smell. It is widely used in fertilizers, refrigerants, explosives, cleaning agents, and is a precursor for numeous chemicals. Biologically, it is a common nitrogenous waste, and it contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to fertilisers. Around 70% of ammonia produced industrially is used to make fertilisers in various forms and composition, such as urea and diammonium phosphate. Ammonia in pure form is also applied directly into the soil. Ammonia, either directly or indirectly, is also a building block for the synthesis of many chemicals. In many countries, it is classified as an List of extremely hazardous substances, extremely hazardous substance. Ammonia is toxic, cau ...
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Sodium Amide
Sodium amide, commonly called sodamide (systematic name sodium azanide), is the inorganic compound with the formula . It is a salt composed of the sodium cation and the azanide anion. This solid, which is dangerously reactive toward water, is white, but commercial samples are typically gray due to the presence of small quantities of metallic iron from the manufacturing process. Such impurities do not usually affect the utility of the reagent. conducts electricity in the fused state, its conductance being similar to that of NaOH in a similar state. has been widely employed as a strong base in organic synthesis. Preparation and structure Sodium amide can be prepared by the reaction of sodium with ammonia gas, but it is usually prepared by the reaction in liquid ammonia using iron(III) nitrate as a catalyst. The reaction is fastest at the boiling point of the ammonia, c. −33 °C. An electride, , is formed as a reaction intermediate. : is a salt-like material and as su ...
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Elimination Reaction
An elimination reaction is a type of organic reaction in which two substituents are removed from a molecule in either a one- or two-step mechanism. The one-step mechanism is known as the E2 reaction, and the two-step mechanism is known as the E1 reaction. The numbers refer not to the number of steps in the mechanism, but rather to the kinetics of the reaction: E2 is bimolecular (second-order) while E1 is unimolecular (first-order). In cases where the molecule is able to stabilize an anion but possesses a poor leaving group, a third type of reaction, E1cB-elimination reaction, E1CB, exists. Finally, the pyrolysis of xanthate and acetate esters proceed through an "internal" elimination mechanism, the Ei mechanism, Ei mechanism. E2 mechanism The E2 mechanism, where E2 stands for bimolecular elimination, involves a one-step mechanism in which ''carbon-hydrogen'' and ''carbon-halogen'' bonds break to form a double bond (''C=C molecular geometry, Pi bond''). The specifics of the re ...
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