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Electrophilic Aromatic Bromination
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 wit ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organic Chemistry
Organic chemistry is a subdiscipline within chemistry involving the science, scientific study of the structure, properties, and reactions of organic compounds and organic matter, organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J.; Greeves, N. and Warren, S. (2012) ''Organic Chemistry''. Oxford University Press. pp. 1–15. . Study of structure determines their structural formula. Study of properties includes Physical property, physical and Chemical property, chemical properties, and evaluation of Reactivity (chemistry), chemical reactivity to understand their behavior. The study of organic reactions includes the organic synthesis, chemical synthesis of natural products, drugs, and polymers, and study of individual organic molecules in the laboratory and via theoretical (in silico) study. The range of chemicals studied chemistry includes hydrocarbons (compounds containing only carbon and hydrogen) as well as compounds based on carbon, but a ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Nitric Acid
Nitric acid is an inorganic compound with the formula . It is a highly corrosive mineral acid. The compound is colorless, but samples tend to acquire a yellow cast over time due to decomposition into nitrogen oxide, oxides of nitrogen. Most commercially available nitric acid has a concentration of 68% in water. When the solution contains more than 86% , it is referred to as ''fuming nitric acid''. Depending on the amount of nitrogen dioxide present, fuming nitric acid is further characterized as red fuming nitric acid at concentrations above 86%, or white fuming nitric acid at concentrations above 95%. Nitric acid is the primary reagent used for nitration – the addition of a nitro group, typically to an organic molecule. While some resulting nitro compounds are shock- and thermally-sensitive explosives, a few are stable enough to be used in munitions and demolition, while others are still more stable and used as synthetic dyes and medicines (e.g. metronidazole). Nitric acid is ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cresol
Cresols (also known as hydroxytoluene, toluenol, benzol or cresylic acid) are a group of aromatic organic compounds. They are widely-occurring phenols (sometimes called ''phenolics'') which may be either natural or manufactured. They are also categorized as methyl phenols. Cresols commonly occur as either solids or liquids because their melting points are generally close to room temperature. Like other types of phenols, they are slowly oxidized by exposure to air, and the resulting impurities often give the samples a yellow to brownish red tint. Cresols have an odor characteristic to that of other simple phenols, reminiscent to some of a "coal tar" smell. The name "cresol" is an adduct of phenol and their traditional source, creosote. Structure and production In its chemical structure, a molecule of cresol has a methyl group substituted onto the ring of phenol. There are three forms ( isomers) of cresol: ''ortho''-cresol ( ''o''-cresol), ''meta''-cresol ( ''m''-cresol), and ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Amine
In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of electrons. Amines can also exist as hetero cyclic compounds. Aniline is the simplest aromatic amine, consisting of a benzene ring bonded to an amino group. Amines are classified into three types: primary (1°), secondary (2°), and tertiary (3°) amines. Primary amines (1°) contain one alkyl or aryl substituent and have the general formula RNH2. Secondary amines (2°) have two alkyl or aryl groups attached to the nitrogen atom, with the general formula R2NH. Tertiary amines (3°) contain three substituent groups bonded to the nitrogen atom, and are represented by the formula R3N. The functional group present in primary amines is called the amino group. Classification of amines Amines can be classified according to the nature and number o ... [...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 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. Diaryliodo ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Activation Energy
In the Arrhenius model of reaction rates, activation energy is the minimum amount of energy that must be available to reactants for a chemical reaction to occur. The activation energy (''E''a) of a reaction is measured in kilojoules per mole (kJ/mol) or kilocalories per mole (kcal/mol). Activation energy can be thought of as a magnitude of the potential barrier (sometimes called the energy barrier) separating minima of the potential energy surface pertaining to the initial and final thermodynamic state. For a chemical reaction to proceed at a reasonable rate, the temperature of the system should be high enough such that there exists an appreciable number of molecules with translational energy equal to or greater than the activation energy. The term "activation energy" was introduced in 1889 by the Swedish scientist Svante Arrhenius. Other uses Although less commonly used, activation energy also applies to nuclear reactions and various other physical phenomena. Temperature ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Aromaticity
In organic chemistry, aromaticity is a chemical property describing the way in which a conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibits a stabilization stronger than would be expected from conjugation alone. The earliest use of the term was in an article by August Wilhelm Hofmann in 1855. There is no general relationship between aromaticity as a chemical property and the olfactory properties of such compounds. Aromaticity can also be considered a manifestation of cyclic delocalization and of resonance. This is usually considered to be because electrons are free to cycle around circular arrangements of atoms that are alternately single- and double- bonded to one another. This commonly seen model of aromatic rings, namely the idea that benzene was formed from a six-membered carbon ring with alternating single and double bonds (cyclohexatriene), was developed by Kekulé (see History section below). Each bond may be seen as a hybrid of a single bo ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Arenium Ion
An arenium ion in organic chemistry is a cyclohexadienyl cation that appears as a reactive intermediate in electrophilic aromatic substitution. For historic reasons this complex is also called a Wheland intermediate, after American chemist George Willard Wheland (1907–1976). They are also called sigma complexes. The smallest arenium ion is the benzenium ion (), which is protonated benzene. : Two hydrogen atoms bonded to one carbon lie in a plane perpendicular to the benzene ring. The arenium ion is no longer an aromatic species; however it is relatively stable due to delocalization: the positive charge is delocalized over 3 carbon atoms by the pi system, as depicted on the following resonance structures: : A complexed electrophile can contribute to the stability of arenium ions. Salts of benzenium ion can be isolated when benzene is protonated by the carborane superacid H(CB11H(CH3)5Br6). The benzenium salt is crystalline with thermal stability up to 150 °C. Bond ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Alkenes
In organic chemistry, an alkene, or olefin, is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or at the terminal position. Terminal alkenes are also known as Alpha-olefin, α-olefins. The International Union of Pure and Applied Chemistry (IUPAC) Preferred IUPAC name, recommends using the name "alkene" only for Open-chain compound, 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 compound, 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 ''n'' being a >1 natural number (which is two hydrogens less than the corresponding alkane). When ''n'' is four or more, isomers are possible, ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Selectfluor
Selectfluor, a trademark of Air Products and Chemicals, is a reagent in chemistry that is used as a fluorine donor. This compound is a derivative of the nucleophillic base DABCO. It is a colourless salt that tolerates air and even water. It has been commercialized for use for electrophilic fluorination. Preparation : Selectfluor is synthesized by the ''N''-alkylation of DABCO, diazabicyclo[2.2.2]octane (DABCO) with dichloromethane in a Menshutkin reaction, followed by ion exchange with sodium tetrafluoroborate (replacing the chloride counterion for the tetrafluoroborate). The resulting salt is treated with elemental fluorine and sodium tetrafluoroborate: The cation is often depicted with one skewed ethylene ((CH2)2) group. In fact, these pairs of CH2 groups are eclipsed so that the cation has idealized C3h symmetry group, symmetry. Mechanism of fluorination Electrophilic fluorinating reagents could in principle operate by electron transfer pathways or an SN2 reaction, SN2 attack ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Benzoic Acid
Benzoic acid () is a white (or colorless) solid organic compound with the formula , whose structure consists of a benzene ring () with a carboxyl () substituent. The benzoyl group is often abbreviated "Bz" (not to be confused with "Bn," which is used for benzyl), thus benzoic acid is also denoted as BzOH, since the benzoyl group has the formula –. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin, which was for a long time its only source. Benzoic acid occurs naturally in many plants and serves as an intermediate in the biosynthesis of many secondary metabolites. Salts of benzoic acid are used as food preservatives. Benzoic acid is an important precursor for the industrial synthesis of many other organic substances. The salts and esters of benzoic acid are known as benzoates (). History Benzoic acid was discovered in the sixteenth century. The dry distillation of gum benzoin was first described by Nostradamus (1556), and then by ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
