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Hydration (chemistry)
In chemistry, a hydration reaction is a chemical reaction in which a substance combines with water. In organic chemistry, water is added to an unsaturated substrate, which is usually an alkene or an alkyne. This type of reaction is employed industrially to produce ethanol, isopropanol, and butan-2-ol.. Organic chemistry Any unsaturated organic compound is susceptible to hydration. Epoxides to glycol Several million tons of ethylene glycol are produced annually by the hydration of oxirane, a cyclic compound also known as ethylene oxide: : C2H4O + H2O → HO–CH2CH2–OH Acid catalysts are typically used. Alkenes The general chemical equation for the hydration of alkenes is the following: :RRC=CH2 + H2O → RRC(OH)-CH3 A hydroxyl group (OH−) attaches to one carbon of the double bond, and a proton (H+) adds to the other. The reaction is highly exothermic. In the first step, the alkene acts as a nucleophile and attacks the proton, following Markovnikov's rule. In the second ...
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Chemistry
Chemistry is the scientific study of the properties and behavior of matter. It is a physical science within the natural sciences that studies the chemical elements that make up matter and chemical compound, compounds made of atoms, molecules and ions: their composition, structure, properties, behavior and the changes they undergo during chemical reaction, reactions with other chemical substance, substances. Chemistry also addresses the nature of chemical bonds in chemical compounds. In the scope of its subject, chemistry occupies an intermediate position between physics and biology. It is sometimes called the central science because it provides a foundation for understanding both Basic research, basic and Applied science, applied scientific disciplines at a fundamental level. For example, chemistry explains aspects of plant growth (botany), the formation of igneous rocks (geology), how atmospheric ozone is formed and how environmental pollutants are degraded (ecology), the prop ...
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Molecule
A molecule is a group of two or more atoms that are held together by Force, attractive forces known as chemical bonds; depending on context, the term may or may not include ions that satisfy this criterion. In quantum physics, organic chemistry, and biochemistry, the distinction from ions is dropped and ''molecule'' is often used when referring to polyatomic ions. A molecule may be homonuclear, that is, it consists of atoms of one chemical element, e.g. two atoms in the oxygen molecule (O2); or it may be heteronuclear, a chemical compound composed of more than one element, e.g. water (molecule), water (two hydrogen atoms and one oxygen atom; H2O). In the kinetic theory of gases, the term ''molecule'' is often used for any gaseous particle regardless of its composition. This relaxes the requirement that a molecule contains two or more atoms, since the noble gases are individual atoms. Atoms and complexes connected by non-covalent interactions, such as hydrogen bonds or ionic ...
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Hydroalkoxylation
Hydroalkoxylation is a chemical reaction that combines alcohols with alkenes or alkynes. The process affords ethers. The reaction converts alkenes to dialkyl or aryl-alkyl ethers: :R'OH + RCH=CH2 → R'OCH(R)-CH3 Similarly, alkynes are converted to vinyl ethers: :R'OH + RC≡CH → R'OC(R)=CH2 As shown, the reaction follows the Markovnikov rule. The process exhibits good atom-economy in the sense that no byproducts are produced. The reaction is catalyzed by bases and also by transition metal complexes. Usually symmetrical ethers are prepared by dehydration of alcohols and unsymmetrical ethers by the Williamson ether synthesis The Williamson ether synthesis is an organic reaction, forming an ether from an organohalide and a deprotonated alcohol (alkoxide). This reaction was developed by Alexander Williamson in 1850. Typically it involves the reaction of an alkoxide ... from alkyl halides and alkali metal alkoxides.Wilhelm Heitmann, Günther Strehlke, Dieter Mayer "Ethers, Ali ...
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Hydroamination
In organic chemistry, hydroamination is the formal Addition reaction, addition of an bond of an amine across an Carbon–carbon bond, carbon-carbon multiple bond of an alkene, alkyne, diene, or allene. In the ideal case, hydroamination is Atom economy, atom economical and Green chemistry, green; and the products could see extensive use in fine-chemical, pharmaceutical, and agricultural industries. Hydroamination reactions occur spontaneously only for electrophilic alkenes and some dienes, but these are known by other names (e.g. Michael addition reaction); "hydroamination" is generally reserved for situations where the reaction requires a catalyst. Hydroamination is however of little value industrially. Hydroamination can be used Intramolecular reaction, intramolecularly to create Heterocyclic compounds, heterocycles or intermolecularly with a separate amine and unsaturated compound. File:Examples of intermolecular hydroamination.png, alt=Prototypical intermolecular hydroaminatio ...
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Geminal Diol
A geminal diol (or gem-diol for short) is any organic compound having two hydroxyl functional groups () bound to the same carbon atom. Geminal diols are a subclass of the diols, which in turn are a special class of alcohols. Most of the geminal diols are considered unstable. The simplest geminal diol is methanediol or . Other examples are: * dihydroxymalinic acid * decahydroxycyclopentane *chloral hydrate Reactions Hydration equilibrium Geminal diols can be viewed as ketone (or aldehyde) hydrates. The two hydroxyl groups in a geminal diol are easily converted to a carbonyl or keto group C=O by loss of one water molecule. Conversely, a keto group can combine with water to form the geminal hydroxyl groups. The equilibrium in water solution may be shifted towards either compound. For example, the equilibrium constant for the conversion of acetone to propane-2,2-diol is about 10−3, while that of formaldehyde to methanediol is 103.Eric V. Anslyn, Dennis A. Dougherty ( ...
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Fermentation
Fermentation is a type of anaerobic metabolism which harnesses the redox potential of the reactants to make adenosine triphosphate (ATP) and organic end products. Organic molecules, such as glucose or other sugars, are catabolized and reduced by donating their electrons to other organic molecules (cofactors, coenzymes, etc.). Fermentation is important in several areas of human society. Humans have used fermentation in the production and preservation of food for 13,000 years. It has been associated with health benefits, unique flavor profiles, and making products have better texture. Humans and their livestock also benefit from fermentation from the microbes in the gut that release end products that are subsequently used by the host for energy. Perhaps the most commonly known use for fermentation is at an industrial level to produce commodity chemicals, such as ethanol and lactate. Ethanol is used in a variety of alcoholic beverages (beers, wine, and spirits) while lactate ...
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Mukaiyama Hydration
The Mukaiyama hydration is an organic reaction involving formal addition of an equivalent of water across an olefin by the action of catalytic bis(acetylacetonato)cobalt(II) complex, phenylsilane and atmospheric oxygen to produce an alcohol with Markovnikov selectivity. The reaction was developed by Teruaki Mukaiyama at Mitsui Petrochemical Industries, Ltd. Its discovery was based on previous work on the selective hydrations of olefins catalyzed by cobalt complexes with Schiff base ligands and porphyrin ligands. Due to its chemoselectivity (tolerant of other functional groups) and mild reactions conditions (run under air at room temperature), the Mukaiyama hydration has become a valuable tool in chemical synthesis. Mechanism In his original publication, Mukaiyama proposed that the reaction proceeded through the intermediacy of a cobalt peroxide adduct. A metal exchange reaction between a hydrosilane and the cobalt peroxide adduct leads to a silyl peroxide, which is converted to ...
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Oxymercuration Reaction
In organic chemistry, the oxymercuration reaction is an electrophilic addition reaction that transforms an alkene () into a neutral alcohol. In oxymercuration, the alkene reacts with mercuric acetate () in aqueous solution to yield the addition of an acetoxymercury () group and a hydroxy () group across the double bond. Carbocations are not formed in this process and thus rearrangements are not observed. The reaction follows Markovnikov's rule (the hydroxy group will always be added to the more substituted carbon). The oxymercuration part of the reaction involves anti addition of OH group but the demercuration part of the reaction involves free radical mechanism and is not stereospecific, i.e. H and OH may be syn or anti to each other. Oxymercuration followed by reductive demercuration is called an oxymercuration–reduction reaction or oxymercuration–demercuration reaction. This reaction, which is almost always done in practice instead of oxymercuration, is treated at the ...
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Hydroboration–oxidation Reaction
Hydroboration–oxidation reaction is a two-step hydration reaction that converts an alkene into an alcohol. The process results in the syn addition of a hydrogen and a hydroxyl group where the double bond had been. Hydroboration–oxidation is an anti-Markovnikov reaction, with the hydroxyl group attaching to the less-substituted carbon. The reaction thus provides a more stereospecific and complementary regiochemical alternative to other hydration reactions such as acid-catalyzed addition and the oxymercuration–reduction process. The reaction was first reported by Herbert C. Brown in the late 1950s and it was recognized in his receiving the Nobel Prize in Chemistry in 1979. The general form of the reaction is as follows: Tetrahydrofuran (THF) is the archetypal solvent used for hydroboration. Mechanism and scope Hydroboration step In the first step, borane (BH3) adds to the double bond, transferring one of the hydrogen atoms to the carbon adjacent to the one that becom ...
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Alkene Hydration Reaction
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 α-olefins. 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 ''n'' being a >1 natural number (which is two hydrogens less than the corresponding alkane). When ''n'' is four or more, isomers are possible, distinguished by the position and conformation of the double bond. A ...
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Solid Acid
Solid acids are acids that are insoluble in the reaction medium. They are often used as heterogeneous catalysts. Many solid acids are zeolites. A variety of techniques are used to quantify the strength of solid acids. Examples Examples of inorganic solid acids include silico-aluminates (zeolites, alumina, silico-aluminophosphate), and sulfated zirconia. Many transition metal oxides are acidic, including titania, zirconia, and niobia. Such acids are used in cracking. Many solid Brønsted acids are also employed industrially, including polystyrene sulfonate, solid phosphoric acid, niobic acid, and hetero polyoxometallates. Applications Solid acids are used in catalysis in many industrial chemical processes, from large-scale catalytic cracking in petroleum refining to the synthesis of various fine chemicals. One large scale application is alkylation, e.g., the combination of benzene and ethylene to give ethylbenzene. Another application is the rearrangement of cyclohex ...
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Phosphoric Acid
Phosphoric acid (orthophosphoric acid, monophosphoric acid or phosphoric(V) acid) is a colorless, odorless phosphorus-containing solid, and inorganic compound with the chemical formula . It is commonly encountered as an 85% aqueous solution, which is a colourless, odourless, and non- volatile syrupy liquid. It is a major industrial chemical, being a component of many fertilizers. The compound is an acid. Removal of all three ions gives the phosphate ion . Removal of one or two protons gives dihydrogen phosphate ion , and the hydrogen phosphate ion , respectively. Phosphoric acid forms esters, called organophosphates. The name "orthophosphoric acid" can be used to distinguish this specific acid from other " phosphoric acids", such as pyrophosphoric acid. Nevertheless, the term "phosphoric acid" often means this specific compound; and that is the current IUPAC nomenclature. Production Phosphoric acid is produced industrially by one of two routes, wet processes and dry. ...
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