Halogenated
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Halogenated
In chemistry, halogenation is a chemical reaction that entails the introduction of one or more halogens into a compound. Halide-containing compounds are pervasive, making this type of transformation important, e.g. in the production of polymers, drugs. This kind of conversion is in fact so common that a comprehensive overview is challenging. This article mainly deals with halogenation using elemental halogens (F2, Cl2, Br2, I2). Halides are also commonly introduced using salts of the halides and halogen acids. Many specialized reagents exist for and introducing halogens into diverse substrates, e.g. thionyl chloride. Organic chemistry Several pathways exist for the halogenation of organic compounds, including free radical halogenation, ketone halogenation, electrophilic halogenation, and halogen addition reaction. The nature of the substrate determines the pathway. The facility of halogenation is influenced by the halogen. Fluorine and chlorine are more electrophilic and ...
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Ketone Halogenation
In organic chemistry, α-keto halogenation is a special type of halogenation. The reaction may be carried out under either acidic or basic conditions in an aqueous medium with the corresponding elemental halogen. In this way, chloride, bromide, and iodide (but notably not fluoride) functionality can be inserted selectively in the alpha position of a ketone. The position alpha to the carbonyl group in a ketone is easily halogenated. This is due to its ability to form an enolate in basic solution, or an enol in acidic solution. An example of alpha halogenation is the mono-bromination of acetone, carried out under either acidic or basic conditions, to give bromoacetone: Acidic (in acetic acid): Basic (in aqueous NaOH): In acidic solution, usually only one alpha hydrogen is replaced by a halogen, as each successive halogenation is slower than the first. The halogen decreases the basicity of the carbonyl oxygen, thus making protonation less favorable. However, in basic solut ...
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Halogen
The halogens () are a group in the periodic table consisting of five or six chemically related elements: fluorine (F), chlorine (Cl), bromine (Br), iodine (I), astatine (At), and tennessine (Ts). In the modern IUPAC nomenclature, this group is known as group 17. The word "halogen" means "salt former" (or "salt maker"). When halogens react with metals, they produce a wide range of salts, including calcium fluoride, sodium chloride (common table salt), silver bromide and potassium iodide. The group of halogens is the only periodic table group that contains elements in three of the main states of matter at standard temperature and pressure. All of the halogens form acids when bonded to hydrogen. Most halogens are typically produced from minerals or salts. The middle halogens—chlorine, bromine, and iodine—are often used as disinfectants. Organobromides are the most important class of flame retardants, while elemental halogens are dangerous and can be toxic. History The fl ...
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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 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 contributes ...
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Iodine Number
Iodine is a chemical element with the symbol I and atomic number 53. The heaviest of the stable halogens, it exists as a semi-lustrous, non-metallic solid at standard conditions that melts to form a deep violet liquid at , and boils to a violet gas at . The element was discovered by the French chemist Bernard Courtois in 1811 and was named two years later by Joseph Louis Gay-Lussac, after the Ancient Greek 'violet-coloured'. Iodine occurs in many oxidation states, including iodide (I−), iodate (), and the various periodate anions. It is the least abundant of the stable halogens, being the sixty-first most abundant element. As the heaviest essential mineral nutrient, iodine is required for the synthesis of thyroid hormones. Iodine deficiency affects about two billion people and is the leading preventable cause of intellectual disabilities. The dominant producers of iodine today are Chile and Japan. Due to its high atomic number and ease of attachment to organic compoun ...
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Iodine
Iodine is a chemical element with the symbol I and atomic number 53. The heaviest of the stable halogens, it exists as a semi-lustrous, non-metallic solid at standard conditions that melts to form a deep violet liquid at , and boils to a violet gas at . The element was discovered by the French chemist Bernard Courtois in 1811 and was named two years later by Joseph Louis Gay-Lussac, after the Ancient Greek 'violet-coloured'. Iodine occurs in many oxidation states, including iodide (I−), iodate (), and the various periodate anions. It is the least abundant of the stable halogens, being the sixty-first most abundant element. As the heaviest essential mineral nutrient, iodine is required for the synthesis of thyroid hormones. Iodine deficiency affects about two billion people and is the leading preventable cause of intellectual disabilities. The dominant producers of iodine today are Chile and Japan. Due to its high atomic number and ease of attachment to organic compound ...
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Bromine
Bromine is a chemical element with the symbol Br and atomic number 35. It is the third-lightest element in group 17 of the periodic table (halogens) and is a volatile red-brown liquid at room temperature that evaporates readily to form a similarly coloured vapour. Its properties are intermediate between those of chlorine and iodine. Isolated independently by two chemists, Carl Jacob Löwig (in 1825) and Antoine Jérôme Balard (in 1826), its name was derived from the Ancient Greek (bromos) meaning "stench", referring to its sharp and pungent smell. Elemental bromine is very reactive and thus does not occur as a native element in nature but it occurs in colourless soluble crystalline mineral halide salts, analogous to table salt. In fact, bromine and all the halogens are so reactive that they form bonds in pairs—never in single atoms. While it is rather rare in the Earth's crust, the high solubility of the bromide ion (Br) has caused its accumulation in the oceans. Commercial ...
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Bromoperoxidase
Bromide peroxidase (, ''bromoperoxidase'', ''haloperoxidase (ambiguous)'', ''eosinophil peroxidase'') is a family of enzymes with systematic name ''bromide:hydrogen-peroxide oxidoreductase''. These enzymes catalyses the following chemical reaction: : HBr + H2O2 \rightleftharpoons HOBr + H2O The HOBr is a potent brominating agent. The many organobromine compounds observed in marine environments are the products of reaction with this oxidized form of bromine. Bromo peroxidases of red and brown marine algae (''Rhodophyta'' and ''Phaeophyta'') contain vanadate (vanadium bromoperoxidase). Otherwise vanadium is unusual cofactor in biology. By virtue of this family of enzymes, a variety of brominated natural products have been isolated from marine sources. Related chloroperoxidase enzymes effect chlorination. In the nomenclature of haloperoxidase, bromoperoxidases classically are unable to oxidize chloride at all. For example, eosinophil peroxidase appears to prefer bromide ove ...
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Iodoform Reaction
In chemistry, the haloform reaction is a chemical reaction in which a haloform (, where X is a halogen) is produced by the exhaustive halogenation of an acetyl group (, where R can be either a hydrogen atom, an alkyl or an aryl group), in the presence of a base. The reaction can be used to transform acetyl groups into carboxyl groups () or to produce chloroform (), bromoform (), or iodoform (). Note that fluoroform () can't be prepared in this way. Mechanism In the first step, the halogen dis-proportionates in the presence of hydroxide to give the halide and hypohalite. :Br2 + 2 OH- -> Br- + BrO- + H2O If a secondary alcohol is present, it is oxidized to a ketone by the hypohalite: If a methyl ketone is present, it reacts with the hypohalite in a three-step process: 1. Under basic conditions, the ketone undergoes keto-enol tautomerisation. The enolate undergoes electrophilic attack by the hypohalite (containing a halogen with a formal +1 charge). : 2. When the α(alph ...
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Trichloroethylene
The chemical compound trichloroethylene is a halocarbon commonly used as an industrial solvent. It is a clear, colourless non-flammable liquid with a chloroform-like sweet smell. It should not be confused with the similar 1,1,1-trichloroethane, which is commonly known as ''chlorothene''. The IUPAC name is trichloroethene. Industrial abbreviations include TCE, trichlor, Trike, Tricky and tri. It has been sold under a variety of trade names. Under the trade names Trimar and Trilene, trichloroethylene was used as a volatile anesthetic and as an inhaled obstetrical analgesic in millions of patients. Groundwater and drinking water contamination from industrial discharge including trichloroethylene is a major concern for human health and has precipitated numerous incidents and lawsuits. History Pioneered by Imperial Chemical Industries in Britain, its development was hailed as an anesthetic revolution. Originally thought to possess less hepatotoxicity than chloroform, and without th ...
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Halothane
Halothane, sold under the brand name Fluothane among others, is a general anaesthetic. It can be used to induce or maintain anaesthesia. One of its benefits is that it does not increase the production of saliva, which can be particularly useful in those who are difficult to intubate. It is given by inhalation. Side effects include an irregular heartbeat, respiratory depression, and hepatotoxicity. Like all volatile anesthetics, it should not be used in people with a personal or family history of malignant hyperthermia. It appears to be safe in porphyria. It is unclear whether use during pregnancy is harmful to the baby, and it is not generally recommended for use during a C-section. Halothane is a chiral molecule that is used as a racemic mixture. Halothane was discovered in 1955. It was approved for medical use in the United States in 1958. It is on the World Health Organization's List of Essential Medicines. Its use in developed countries has been mostly replaced by newer ane ...
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Halothane Synthesis
Halothane, sold under the brand name Fluothane among others, is a general anaesthetic. It can be used to induce or maintain anaesthesia. One of its benefits is that it does not increase the production of saliva, which can be particularly useful in those who are difficult to intubate. It is given by inhalation. Side effects include an irregular heartbeat, respiratory depression, and hepatotoxicity. Like all volatile anesthetics, it should not be used in people with a personal or family history of malignant hyperthermia. It appears to be safe in porphyria. It is unclear whether use during pregnancy is harmful to the baby, and it is not generally recommended for use during a C-section. Halothane is a chiral molecule that is used as a racemic mixture. Halothane was discovered in 1955. It was approved for medical use in the United States in 1958. It is on the World Health Organization's List of Essential Medicines. Its use in developed countries has been mostly replaced by newer ane ...
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Chemical Selectivity
Chemoselectivity is the preferential outcome of a chemical reaction over a set of possible alternative reactions. In another definition, chemoselectivity refers to the selective reactivity of one functional group in the presence of others; often this process in convoluted and protecting groups are on the molecular connectivity alone. Such predictions based on connectivity are generally considered plausible, but the physical outcome of the actual reaction is ultimately dependent on a number of factors that are practically impossible to predict to any useful accuracy (solvent, atomic orbitals, etc.). Chemoselectivity can be difficult to predict, but observing selective outcomes in cases where many reactions are plausible, is common. Examples include the selective organic reduction of the greater relative chemoselectivity of sodium borohydride reduction versus lithium aluminium hydride reduction. In another example, the compound 4-methoxyacetophenone is oxidized by bleach at the ...
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