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Methanesulfonic Anhydride
Methanesulfonic anhydride (Ms2O) is the acid anhydride of methanesulfonic acid. Like methanesulfonyl chloride (MsCl), it may be used to generate mesylates (methanesulfonyl esters). Preparation & purification Ms2O may be prepared by the dehydration of methanesulfonic acid with phosphorus pentoxide. :P2O5 + 6 CH3SO3H → 3 (CH3SO2)2O + 2 H3PO4 Ms2O can be purified by distillation under vacuum (distillation of a solid) or by recrystallized from Methyl tert-butyl ether/toluene. Reactions & Applications in synthesis Passage of hydrogen chloride through molten Ms2O yields MsCl. Similar to MsCl, Ms2O can perform mesylation of alcohols to form sulfonates. Use of Ms2O avoids the alkyl chloride, which often appears as a side-product when MsCl is used. Unlike MsCl, Ms2O may not be suitable for mesylation of the unsaturated alcohols. Examples of mesylation of alcohols with Ms2O: * Octadecyl methanesulfonate was prepared from octadecanol in pyridine. * Secondary alcohol at the anomeric c ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hydrolysis
Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolysis is the cleavage of biomolecules where a water molecule is consumed to effect the separation of a larger molecule into component parts. When a carbohydrate is broken into its component sugar molecules by hydrolysis (e.g., sucrose being broken down into glucose and fructose), this is recognized as saccharification. Hydrolysis reactions can be the reverse of a condensation reaction in which two molecules join into a larger one and eject a water molecule. Thus hydrolysis adds water to break down, whereas condensation builds up by removing water. Types Usually hydrolysis is a chemical process in which a molecule of water is added to a substance. Sometimes this addition causes both the substance and w ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Triflate
In organic chemistry, triflate (systematic name: trifluoromethanesulfonate), is a functional group with the formula and structure . The triflate group is often represented by , as opposed to −Tf, which is the triflyl group, . For example, ''n''-butyl triflate can be written as . The corresponding triflate anion, , is an extremely stable polyatomic ion; this comes from the fact that triflic acid () is a superacid; i.e. it is more acidic than pure sulfuric acid, already one of the strongest acids known. Applications A triflate group is an excellent leaving group used in certain organic reactions such as nucleophilic substitution, Suzuki couplings and Heck reactions. Since alkyl triflates are extremely reactive in SN2 reactions, they must be stored in conditions free of nucleophiles (such as water). The anion owes its stability to resonance stabilization which causes the negative charge to be spread symmetrically over the three oxygen atoms. An additional stabilization is a ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Sulfuric Acid
Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid ( Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen and hydrogen, with the molecular formula . It is a colorless, odorless and viscous liquid that is miscible with water. Pure sulfuric acid does not exist naturally on Earth due to its strong affinity to water vapor; it is hygroscopic and readily absorbs water vapor from the air. Concentrated sulfuric acid is highly corrosive towards other materials, from rocks to metals, since it is an oxidant with powerful dehydrating properties. Phosphorus pentoxide is a notable exception in that it is not dehydrated by sulfuric acid, but to the contrary dehydrates sulfuric acid to sulfur trioxide. Upon addition of sulfuric acid to water, a considerable amount of heat is released; thus the reverse procedure of adding water to the acid should not be performed since the heat released may boi ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
1,3-Dichlorobenzene
1,3-Dichlorobenzene (also known as meta-dichlorobenzene) is an organic compound with the formula C6H4Cl2. It is the least common of the three isomers of dichlorobenzene, and it is a colorless liquid that is insoluble in water. It is produced as a minor byproduct of the chlorination of benzene, but can also be prepared in a directed manner by the Sandmeyer reaction of 3-chloroaniline. It also arises from the isomerization of the other dichlorobenzenes at high temperature. Hazards This chemical is combustible. "Hazardous decomposition products" are carbon monoxide, carbon dioxide, chlorine, hydrogen chloride gas. It is toxic to aquatic life with long-lasting effects. See also Other isomers: * 1,2-Dichlorobenzene * 1,4-Dichlorobenzene Other halides: * Dibromobenzene Dibromobenzene may refer to: * 1,2-Dibromobenzene (''o''-dibromobenzene) * 1,3-Dibromobenzene (''m''-dibromobenzene) * 1,4-Dibromobenzene 1,4-Dibromobenzene (''p''-dibromobenzene) is an organic compound that i ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Arene Substitution Pattern
Arene substitution patterns are part of organic chemistry IUPAC nomenclature and pinpoint the position of substituents other than hydrogen in relation to each other on an aromatic hydrocarbon. ''Ortho'', ''meta'', and ''para'' substitution * In ''ortho''-substitution, two substituents occupy positions next to each other, which may be numbered 1 and 2. In the diagram, these positions are marked R and ''ortho''. * In ''meta''-substitution the substituents occupy positions 1 and 3 (corresponding to R and ''meta'' in the diagram). * In ''para''-substitution, the substituents occupy the opposite ends (positions 1 and 4, corresponding to R and ''para'' in the diagram). The toluidines serve as an example for these three types of substitution. Synthesis Electron donating groups, for example amino, hydroxyl, alkyl, and phenyl groups tend to be ''ortho''/''para''-directors, and electron withdrawing groups such as nitro, nitrile, and ketone groups, tend to be ''meta''-directors. Propert ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Chlorobenzene
Chlorobenzene is an aromatic organic compound with the chemical formula C6H5Cl. This colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals. Uses Historical The major use of chlorobenzene is as an intermediate in the production of herbicides, dyestuffs, and rubber. Chlorobenzene is also used as a high-boiling solvent in industrial applications as well as in the laboratory. Chlorobenzene is nitrated on a large scale to give a mixture of 2-nitrochlorobenzene and 4-nitrochlorobenzene, which are separated. These mononitrochlorobenzenes are converted to related 2-nitrophenol, 2-nitroanisole, bis(2-nitrophenyl)disulfide, and 2-nitroaniline by nucleophilic displacement of the chloride, with respectively sodium hydroxide, sodium methoxide, sodium disulfide, and ammonia. The conversions of the 4-nitro derivative are similar. Chlorobenzene once was used in the manufacture of pesticides, most notably DDT, by reaction with ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Benzene
Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, benzene is classed as a hydrocarbon. Benzene is a natural constituent of petroleum and is one of the elementary petrochemicals. Due to the cyclic continuous pi bonds between the carbon atoms, benzene is classed as an aromatic hydrocarbon. Benzene is a colorless and highly flammable liquid with a sweet smell, and is partially responsible for the aroma of gasoline. It is used primarily as a precursor to the manufacture of chemicals with more complex structure, such as ethylbenzene and cumene, of which billions of kilograms are produced annually. Although benzene is a major industrial chemical, it finds limited use in consumer items because of its toxicity. History Discovery The word "''benzene''" derives from "''gum benzoin''" (benzoin res ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Electrophilic Aromatic Directing Groups
In electrophilic aromatic substitution reactions, existing substituent groups on the aromatic ring influence the overall reaction rate or have a directing effect on positional isomer of the products that are formed. An electron donating group (EDG) or electron releasing group (ERG, Z in structural formulas) is an atom or functional group that donates some of its electron density into a conjugated π system via resonance (mesomerism) or inductive effects (or induction)—called +M or +I effects, respectively—thus making the π system more nucleophilic. As a result of these electronic effects, an aromatic ring to which such a group is attached is more likely to participate in electrophilic substitution reaction. EDGs are therefore often known as activating groups, though steric effects can interfere with the reaction. An electron withdrawing group (EWG) will have the opposite effect on the nucleophilicity of the ring. The EWG removes electron density from a π system, making it le ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Aryl
In organic chemistry, an aryl is any functional group or substituent derived from an aromatic ring, usually an aromatic hydrocarbon, such as phenyl and naphthyl. "Aryl" is used for the sake of abbreviation or generalization, and "Ar" is used as a placeholder for the aryl group in chemical structure diagrams, analogous to “R” used for any organic substituent. “Ar” is not to be confused with the elemental symbol for argon. A simple aryl group is phenyl (), a group derived from benzene. Examples of other aryl groups consist of: * The tolyl group () which is derived from toluene (methylbenzene) * The xylyl group (), which is derived from xylene (dimethylbenzene) * The naphthyl group (), which is derived from naphthalene Arylation is the process in which an aryl group is attached to a substituent. It is typically achieved by cross-coupling reactions. Nomenclature The most basic aryl group is phenyl, which is made up of a benzene ring with one hydrogen atom substituted ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Friedel–Crafts Reaction
The Friedel–Crafts reactions are a set of reactions developed by Charles Friedel and James Crafts in 1877 to attach substituents to an aromatic ring. Friedel–Crafts reactions are of two main types: alkylation reactions and acylation reactions. Both proceed by electrophilic aromatic substitution. Alkylation With alkyl halides Friedel–Crafts alkylation involves the alkylation of an aromatic ring. Traditionally, the alkylating agents are alkyl halides. Many alkylating agents can be used instead of alkyl halides. For example, enones and epoxides can be used in presence of protons. Traditionally also, the reaction employs a strong Lewis acid, such as aluminium chloride as catalyst. This reaction suffers from the disadvantage that the product is more nucleophilic than the reactant because alkyl groups are activators for the Friedel–Crafts reaction. Consequently, overalkylation can occur. Steric hindrance can be exploited to limit the number of alkylations, as in the ''t ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Lewis Acid Catalysis
In Lewis acid catalysis of organic reactions, a metal-based Lewis acid acts as an electron pair acceptor to increase the reactivity of a substrate. Common Lewis acid catalysts are based on main group metals such as aluminum, boron, silicon, and tin, as well as many early (titanium, zirconium) and late (iron, copper, zinc) d-block metals. The metal atom forms an adduct with a lone-pair bearing electronegative atom in the substrate, such as oxygen (both sp2 or sp3), nitrogen, sulfur, and halogens. The complexation has partial charge-transfer character and makes the lone-pair donor effectively more electronegative, activating the substrate toward nucleophilic attack, heterolytic bond cleavage, or cycloaddition with 1,3-dienes and 1,3-dipoles. Many classical reactions involving carbon–carbon or carbon–heteroatom bond formation can be catalyzed by Lewis acids. Examples include the Friedel-Crafts reaction, the aldol reaction, and various pericyclic processes that proceed slowly at r ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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