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Dehydrohalogenation
In chemistry, dehydrohalogenation is an elimination reaction which removes a hydrogen halide from a substrate (chemistry), substrate. The reaction is usually associated with the synthesis of alkenes, but it has wider applications. Dehydrohalogenation from alkyl halides Traditionally, alkyl halides are substrates for dehydrohalogenations. The alkyl halide must be able to form an alkene, thus halides having no C–H bond on an adjacent carbon are not suitable substrates. Aryl halides are also unsuitable. Upon treatment with strong base, chlorobenzene dehydrohalogenates to give phenol#Hydrolysis of chlorobenzene, phenol via a benzyne intermediate. Base-promoted reactions to alkenes When treated with a strong base many alkyl chlorides convert to corresponding alkene. It is also called a β-elimination reaction and is a type of elimination reaction. Some prototypes are shown below: :\begin \ce\ &\ce \\ \ce\ &\ce \\ \ce\ &\ce \end Here ethyl chloride reacts with potassium hydroxide, ty ...
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Haloalkane
The haloalkanes (also known as halogenoalkanes or alkyl halides) are alkanes containing one or more halogen substituents of hydrogen atom. They are a subset of the general class of halocarbons, although the distinction is not often made. Haloalkanes are widely used commercially. They are used as flame retardants, fire extinguisher, fire extinguishants, refrigerants, propellants, solvents, and pharmaceuticals. Subsequent to the widespread use in commerce, many halocarbons have also been shown to be serious pollutants and toxins. For example, the chlorofluorocarbons have been shown to lead to ozone depletion. Methyl bromide is a controversial fumigant. Only haloalkanes that contain chlorine, bromine, and iodine are a threat to the ozone layer, but fluorinated volatile haloalkanes in theory may have activity as greenhouse gases. Methyl iodide, a naturally occurring substance, however, does not have ozone-depleting properties and the United States Environmental Protection Agency has de ...
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Synthesis Of Alkenes - Dehydrohalogenation
Synthesis or synthesize may refer to: Science Chemistry and biochemistry *Chemical synthesis, the execution of chemical reactions to form a more complex molecule from chemical precursors **Organic synthesis, the chemical synthesis of organic compounds ***Total synthesis, the complete organic synthesis of complex organic compounds, usually without the aid of biological processes *** Convergent synthesis or linear synthesis, a strategy to improve the efficiency of multi-step chemical syntheses **Dehydration synthesis, a chemical synthesis resulting in the loss of a water molecule *Biosynthesis, the creation of an organic compound in a living organism, usually aided by enzymes **Photosynthesis, a biochemical reaction using a carbon molecule to produce an organic molecule, using sunlight as a catalyst **Chemosynthesis, the synthesis of biological compounds into organic waste, using methane or an oxidized molecule as a catalyst **Amino acid synthesis, the synthesis of an amino aci ...
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Regioselectivity
In organic chemistry, regioselectivity is the preference of chemical bonding or breaking in one direction over all other possible directions. It can often apply to which of many possible positions a reagent will affect, such as which proton a strong base will abstract from an organic molecule, or where on a substituted benzene ring a further substituent will be added. A specific example is a halohydrin formation reaction with 2-propenylbenzene: : Because of the preference for the formation of one product over another, the reaction is selective. This reaction is regioselective because it selectively generates one constitutional isomer rather than the other. Various examples of regioselectivity have been formulated as rules for certain classes of compounds under certain conditions, many of which are named. Among the first introduced to chemistry students are Markovnikov's rule for the addition of protic acids to alkenes, and the Fürst-Plattner rule for the addition of ...
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Propylene Oxide
Propylene oxide is an epoxide with the molecular formula C3H6O. This colourless volatile liquid with an odour similar to ether, is produced on a large scale industrially. Its major application is its use for the production of polyether polyols for use in making polyurethane plastics. It is a chiral epoxide, although it is commonly used as a racemic mixture. This compound is sometimes called 1,2-propylene oxide to distinguish it from its isomer 1,3-propylene oxide, better known as oxetane. Production Industrial production of propylene oxide starts from propylene. Two general approaches are employed, one involving chlorohydrin formation and the other involving oxidation. In 2005, about half of the world production was through chlorohydrin technology and one half via oxidation routes. The latter approach is growing in importance. Chlorohydrin route The traditional route proceeds via the conversion of propylene to propylene chlorohydrin according to the following simplified sch ...
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Chlorohydrin
In organic chemistry a halohydrin (also a haloalcohol or β-halo alcohol) is a functional group in which a halogen and a hydroxyl are bonded to adjacent carbon atoms, which otherwise bear only hydrogen or hydrocarbyl groups (e.g. 2-chloroethanol, 3-chloropropane-1,2-diol). The term only applies to saturated motifs, as such compounds like 2-chlorophenol would not normally be considered halohydrins. Megatons of some chlorohydrins, e.g. propylene chlorohydrin, are produced annually as precursors to polymers. Halohydrins may be categorized as chlorohydrins, bromohydrins, fluorohydrins or iodohydrins depending on the halogen present. Synthesis From alkenes Halohydrins are usually prepared by treatment of an alkene with a halogen, in the presence of water. The reaction is a form of electrophilic addition, with the halogen acting as electrophile. In that regard, it resembles the halogen addition reaction and proceeds with anti addition, leaving the newly added X and OH groups in ...
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1,2,3,3,3-Pentafluoropropene
1,2,3,3,3-Pentafluoropropene is the unsaturated fluorocarbon with the formula HFC=C(F)CF. This colorless gas is of interest as a precursor to hydrofluoroolefins (HFOs), which are used as refrigerants in air conditioners. Of the methods reported for its synthesis, one route involves dehydrofluorination In chemistry, dehydrohalogenation is an elimination reaction which removes a hydrogen halide from a substrate. The reaction is usually associated with the synthesis of alkenes, but it has wider applications. Dehydrohalogenation from alkyl hali ... of 1,1,2,3,3,3-hexafluoropropane.Nappa, Mario Joseph; Rao, Velliyur Nott Mallikarjuna "Dehydrofluorination and hydrogenation process and catalysts for the manufacture of 1,1,1,2,3-pentafluoropropane from 1,1,1,2,3,3-hexafluoropropane" PCT Int. Appl. (1994), WO 9427940 A1 19941208. The compound exists as a mixture of E- and Z-isomers. References {{DEFAULTSORT:Pentafluoropropene, 1, 2, 3, 3, 3- Fluoroalkenes Refrigerants Trifluor ...
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Hydrofluoroolefin
Hydrofluoroolefins (HFOs) are Saturated and unsaturated compounds, unsaturated organic compounds composed of hydrogen, fluorine and carbon. These organofluorine compounds are of interest as refrigerants. Unlike traditional hydrofluorocarbons (HFCs) and chlorofluorocarbons (CFCs), which are Saturated and unsaturated compounds, saturated, HFOs are Alkene, olefins, otherwise known as alkenes. HFO refrigerants are categorized as having zero ozone depletion potential (ODP) and low global warming potential (GWP) and so offer a more environmentally friendly alternative to CFC, HCFC, and HFC refrigerants. Compared to HCFCs and HFCs, HFOs have shorter tropospheric lifetimes due to the reactivity of the C=C bond with hydroxyl radicals and chlorine radicals. This quick reactivity prevents them from reaching the stratosphere and participating in the depletion of good ozone, leading to strong interest in the development and characterization of new HFO blends for use as refrigerants. Many refrig ...
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Oxychlorination
In chemistry, oxychlorination is a process for generating the equivalent of chlorine gas (Cl2) from hydrogen chloride and oxygen. This process is attractive industrially because hydrogen chloride is less expensive than chlorine. Mechanism The reaction is usually initiated by copper(II) chloride (CuCl2), which is the most common catalyst in the production of 1,2-dichloroethane. In some cases, CuCl2 is supported on silica in presence of KCl, LaCl3, or AlCl3 as cocatalysts. Aside from silica, a variety of supports have also been used including various types of alumina, diatomaceous earth, or pumice. Because this reaction is highly exothermic (238 kJ/mol), the temperature is monitored, to guard against thermal degradation of the catalyst. The reaction is as follows: :CH2=CH2 + 2 CuCl2 → 2 CuCl + ClH2C-CH2Cl The copper(II) chloride is regenerated by sequential reactions of the cuprous chloride with oxygen and then hydrogen chloride: :½ O2 + 2 CuCl → CuOCuCl2 :2 H ...
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1,2-Dichloroethane
The chemical compound 1,2-dichloroethane, commonly known as ethylene dichloride (EDC), is a chlorinated hydrocarbon. It is a colourless liquid with a chloroform-like odour. The most common use of 1,2-dichloroethane is in the production of vinyl chloride, which is used to make polyvinyl chloride (PVC) pipes, furniture and automobile upholstery, wall coverings, housewares, and automobile parts. 1,2-Dichloroethane is also used generally as an intermediate for other organic chemical compounds, and as a solvent. It forms azeotropes with many other solvents, including water (at a boiling point of ) and other chlorocarbons. History In 1794, physician Jan Rudolph Deiman, merchant Adriaan Paets van Troostwijk, chemist Anthoni Lauwerenburg, and botanist Nicolaas Bondt, under the name of Society of Dutch Chemists (), were the first to produce 1,2-dichloroethane from olefiant gas (oil-making gas, ethylene) and chlorine gas. Although the ''Gezelschap'' in practice did not do much in ...
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Vinyl Chloride
Vinyl chloride is an organochloride with the formula H2C =CHCl. It is also called vinyl chloride monomer (VCM) or chloroethene. It is an important industrial chemical chiefly used to produce the polymer polyvinyl chloride (PVC). Vinyl chloride is a colourless flammable gas that has a sweet odor and is carcinogenic. Vinyl chloride monomer is among the top twenty largest petrochemicals (petroleum-derived chemicals) in world production. The United States remains the largest vinyl chloride manufacturing region because of its low-production-cost position in chlorine and ethylene raw materials. China is also a large manufacturer and one of the largest consumers of vinyl chloride. It can be formed in the environment when soil organisms break down chlorinated solvents. Vinyl chloride that is released by industries or formed by the breakdown of other chlorinated chemicals can enter the air and drinking water supplies. Vinyl chloride is a common contaminant found near landfills. Before the 197 ...
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Dihalide
In chemistry, a halide (rarely halogenide) is a binary chemical compound, of which one part is a halogen atom and the other part is an element or radical that is less electronegative (or more electropositive) than the halogen, to make a fluoride, chloride, bromide, iodide, astatide, or theoretically tennesside compound. The alkali metals combine directly with halogens under appropriate conditions forming halides of the general formula, MX (X = F, Cl, Br or I). Many salts are halides; the ''hal-'' syllable in ''halide'' and ''halite'' reflects this correlation. A halide ion is a halogen atom bearing a negative charge. The common halide anions are fluoride (), chloride (), bromide (), and iodide (). Such ions are present in many ionic halide salts. Halide minerals contain halides. All these halide anions are colorless. Halides also form covalent bonds, examples being colorless TiF4, colorless TiCl4, orange TiBr4, and brown TiI4. The heavier members TiCl4, TiBr4, TiI4 c ...
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Vicinal (chemistry)
In chemistry the descriptor vicinal (from Latin ''vicinus'' = neighbor), abbreviated ''vic'', is a descriptor that identifies two functional groups as bonded to two adjacent carbon atoms (i.e., in a 1,2-relationship). It may arise from vicinal difunctionalization. Relation of atoms in a molecule For example, the molecule 2,3-dibromobutane carries two vicinal bromine Bromine is a chemical element; it has chemical symbol, symbol Br and atomic number 35. It is a volatile red-brown liquid at room temperature that evaporates readily to form a similarly coloured vapour. Its properties are intermediate between th ... atoms and 1,3-dibromobutane does not. Mostly, the use of the term vicinal is restricted to two identical functional groups. Likewise in a ''gem-''dibromide the prefix ''gem'', an abbreviation of '' geminal'', signals that both bromine atoms are bonded to the same carbon atom (i.e., in a 1,1-relationship). For example, 1,1-dibromobutane is geminal. While comparativel ...
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