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Halogenation
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 are m ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Alkenes
In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, and Biological Chemistry'. 1232 pages. Two general types of monoalkenes are distinguished: terminal and internal. Also called α-olefins, terminal alkenes are more useful. However, the International Union of Pure and Applied Chemistry (IUPAC) recommends using the name "alkene" only for acyclic hydrocarbons with just one double bond; alkadiene, alkatriene, etc., or polyene for acyclic hydrocarbons with two or more double bonds; cycloalkene, cycloalkadiene, etc. for cyclic ones; and "olefin" for the general class – cyclic or acyclic, with one or more double bonds. Acyclic alkenes, with only one double bond and no other functional groups (also known as mono-enes) form a homologous series of hydrocarbons with the general formula with '' ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Free Radical Halogenation
In organic chemistry, free-radical halogenation is a type of halogenation. This chemical reaction is typical of alkanes and alkyl-substituted aromatics under application of UV light. The reaction is used for the industrial synthesis of chloroform (CHCl3), dichloromethane (CH2Cl2), and hexachlorobutadiene. It proceeds by a free-radical chain mechanism. General mechanism The chain mechanism is as follows, using the chlorination of methane as a usual example: :1. Initiation: Splitting or homolysis of a chlorine molecule to form two chlorine atoms, initiated by ultraviolet radiation . A chlorine atom has an unpaired electron and acts as a free radical. :: :2. chain propagation (two steps): a hydrogen atom is pulled off from methane leaving a primary methyl radical. The methyl radical then pulls a Cl• from Cl2. :: This results in the desired product plus another chlorine radical. This radical will then go on to take part in another propagation reaction causing a chain reaction. ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Electrophilic Halogenation
In organic chemistry, an electrophilic aromatic halogenation is a type of electrophilic aromatic substitution. This organic reaction is typical of aromatic compounds and a very useful method for adding substituents to an aromatic system. : A few types of aromatic compounds, such as phenol, will react without a catalyst, but for typical benzene derivatives with less reactive substrates, a Lewis acid is required as a catalyst. Typical Lewis acid catalysts include , , and . These work by forming a highly electrophilic complex which is attacked by the benzene ring. Reaction mechanism The reaction mechanism for chlorination of benzene is the same as bromination of benzene. Iron(III) bromide and iron(III) chloride become inactivated if they react with water, including moisture in the air. Therefore, they are generated by adding iron filings to bromine or chlorine. Here is the mechanism of this reaction: : The mechanism for iodination is slightly different: iodine (I2) is treated wi ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Halonium Ion
A halonium ion is any onium ion containing a halogen atom carrying a positive charge. This cation has the general structure where X is any halogen and no restrictions on R, this structure can be cyclic or an open chain molecular structure. Halonium ions formed from fluorine, chlorine, bromine, and iodine are called fluoronium, chloronium, bromonium, and iodonium, respectively. The 3-membered cyclic variety commonly proposed as intermediates in electrophilic halogenation may be called haliranium ions, using the Hantzsch-Widman nomenclature system. Structure The simplest halonium ions are of the structure (X = F, Cl, Br, I). Many halonium ions have a three-atom cyclic structure, similar to that of an epoxide, resulting from the formal addition of a halogenium ion X+ to a C=C double bond, as when a halogen is added to an alkene. The formation of 5-membered halonium ions (e.g., chlorolanium, bromolanium ions) via neighboring group participation is also well studied. Diaryliodoniu ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Thionyl Chloride
Thionyl chloride is an inorganic compound with the chemical formula . It is a moderately volatile, colourless liquid with an unpleasant acrid odour. Thionyl chloride is primarily used as a chlorinating reagent, with approximately per year being produced during the early 1990s, but is occasionally also used as a solvent. It is toxic, reacts with water, and is also listed under the Chemical Weapons Convention as it may be used for the production of chemical weapons. Thionyl chloride is sometimes confused with sulfuryl chloride, , but the properties of these compounds differ significantly. Sulfuryl chloride is a source of chlorine whereas thionyl chloride is a source of chloride ions. Production The major industrial synthesis involves the reaction of sulfur trioxide and sulfur dichloride: This synthesis can be adapted to the laboratory by heating oleum to slowly distill the sulfur trioxide into a cooled flask of sulfur dichloride. :SO3 + SCl2 -> SOCl2 + SO2 Other methods includ ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Halogen Addition Reaction
A halogen addition reaction is a simple organic reaction where a halogen molecule is added to the carbon–carbon double bond of an alkene functional group. The general chemical formula of the halogen addition reaction is: :C=C + X2 → X−C−C−X (X represents the halogens bromine or chlorine, and in this case, a solvent could be CH2Cl2 or CCl4). The product is a vicinal dihalide. This type of reaction is a halogenation and an electrophilic addition. Reaction mechanism The reaction mechanism for an alkene bromination can be described as follows. In the first step of the reaction, a bromine molecule approaches the electron-rich alkene carbon–carbon double bond. The bromine atom closer to the bond takes on a partial positive charge as its electrons are repelled by the electrons of the double bond. The atom is electrophilic at this time and is attacked by the pi electrons of the alkene arbon–carbon double bond It forms for an instant a single sigma bond to ''both'' ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Chlorine
Chlorine is a chemical element with the Symbol (chemistry), symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate between them. Chlorine is a yellow-green gas at room temperature. It is an extremely reactive element and a strong oxidising agent: among the elements, it has the highest electron affinity and the third-highest electronegativity on the revised Electronegativity#Pauling electronegativity, Pauling scale, behind only oxygen and fluorine. Chlorine played an important role in the experiments conducted by medieval Alchemy, alchemists, which commonly involved the heating of chloride Salt (chemistry), salts like ammonium chloride (sal ammoniac) and sodium chloride (common salt), producing various chemical substances containing chlorine such as hydrogen chloride, mercury(II) chloride (corrosive sublimate), and hydrochloric acid (in the form of ). However ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Electrophilic
In chemistry, an electrophile is a chemical species that forms bonds with nucleophiles by accepting an electron pair. Because electrophiles accept electrons, they are Lewis acids. Most electrophiles are positively charged, have an atom that carries a partial positive charge, or have an atom that does not have an octet of electrons. Electrophiles mainly interact with nucleophiles through addition and substitution reactions. Frequently seen electrophiles in organic syntheses include cations such as H+ and NO+, polarized neutral molecules such as HCl, alkyl halides, acyl halides, and carbonyl compounds, polarizable neutral molecules such as Cl2 and Br2, oxidizing agents such as organic peracids, chemical species that do not satisfy the octet rule such as carbenes and radicals, and some Lewis acids such as BH3 and DIBAL. Organic chemistry Addition of halogens These occur between alkenes and electrophiles, often halogens as in halogen addition reactions. Common reaction ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
