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Polyether
In organic chemistry, ethers are a class of compounds that contain an ether group, a single oxygen atom bonded to two separate carbon atoms, each part of an organyl group (e.g., alkyl or aryl). They have the general formula , where R and R′ represent the organyl groups. Ethers can again be classified into two varieties: if the organyl groups are the same on both sides of the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or unsymmetrical ethers. A typical example of the first group is the solvent and anaesthetic diethyl ether, commonly referred to simply as "ether" (). Ethers are common in organic chemistry and even more prevalent in biochemistry, as they are common linkages in carbohydrates and lignin. Structure and bonding Ethers feature bent linkages. In dimethyl ether, the bond angle is 111° and C–O distances are 141  pm. The barrier to rotation about the C–O bonds is low. The bonding of oxy ...
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Valence Bond Theory
In chemistry, valence bond (VB) theory is one of the two basic theories, along with molecular orbital (MO) theory, that were developed to use the methods of quantum mechanics to explain chemical bonding. It focuses on how the atomic orbitals of the dissociated atoms combine to give individual chemical bonds when a molecule is formed. In contrast, molecular orbital theory has orbitals that cover the whole molecule. History In 1916, G. N. Lewis proposed that a chemical bond forms by the interaction of two shared bonding electrons, with the representation of molecules as Lewis structures. The chemist Charles Rugeley Bury suggested in 1921 that eight and eighteen electrons in a shell form stable configurations. Bury proposed that the electron configurations in transitional elements depended upon the valence electrons in their outer shell. In 1916, Kossel put forth his theory of the ionic chemical bond (octet rule), also independently advanced in the same year by Gilbert N. Lew ...
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Aniseed
Anise (; '), also called aniseed or rarely anix, is a flowering plant in the family Apiaceae native to the eastern Mediterranean region and Southwest Asia. The flavor and aroma of its seeds have similarities with some other spices and herbs, such as star anise, fennel, liquorice, and tarragon. It is widely cultivated and used to flavor food, candy, and alcoholic drinks, especially around the Mediterranean. Etymology The name "anise" is derived via Old French from the Latin words or from Greek ''ánēthon'' referring to dill. An obsolete English word for anise is ''anet'', also coming from ''anīsum''. Botany Anise is an herbaceous annual plant growing to or more. The leaves at the base of the plant are simple, long and shallowly lobed, while leaves higher on the stems are feathery or lacy, pinnate, divided into numerous small leaflets. Both leaves and flowers are produced in large, loose clusters. The flowers are either white or yellow, approximately in diameter ...
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Methoxy
In organic chemistry, a methoxy group is the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula . On a benzene ring, the Hammett equation classifies a methoxy substituent at the ''para'' position as an electron-donating group, but as an electron-withdrawing group if at the ''meta'' position. At the ''ortho'' position, steric effects are likely to cause a significant alteration in the Hammett equation prediction, which otherwise follows the same trend as that of the ''para'' position. Occurrence The simplest of methoxy compounds are methanol and dimethyl ether. Other methoxy ethers include anisole and vanillin. Many metal alkoxides contain methoxy groups, such as tetramethyl orthosilicate and titanium methoxide. Esters with a methoxy group can be referred to as methyl esters, and the —COOCH3 substituent is called a methoxycarbonyl. Biosynthesis In nature, methoxy groups are found on nucleosides subjected to 2′-''O''-meth ...
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Methoxyethane
Methoxyethane, also known as ethyl methyl ether, is a colorless gaseous ether with the formula . Unlike the related dimethyl ether and diethyl ether, which are widely used and studied, this mixed alkyl ether has no current applications. It is a structural isomer of isopropyl alcohol Isopropyl alcohol (IUPAC name propan-2-ol and also called isopropanol or 2-propanol) is a colorless, flammable, organic compound with a pungent alcoholic odor. Isopropyl alcohol, an organic polar molecule, is miscible in water, ethanol, an .... Its utility as an anesthetic and solvent have been investigated. References Dialkyl ethers Ether solvents {{Ether-stub ...
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IUPAC Nomenclature
IUPAC nomenclature is a set of recommendations for naming chemical compounds and for describing chemistry and biochemistry in general. The International Union of Pure and Applied Chemistry (IUPAC) is the international authority on chemical nomenclature and terminology. History of the Standardisation of Nomenclature In 1787, Louis-Bernard Guyton de Morveau published his nomenclature recommendations in collaboration with fellow French chemists Berthollet, de Fourcroy and Lavoisier. This work however covered only what are now called inorganic compounds. With the expansion of organic chemistry in the 19th century, and a greater understanding of the structure of organic compounds, the need for a more global standardised nomenclature became more prominent. Following a series of meetings, the first of which was established in 1860 by August Kekulé, the Geneva Nomenclature of 1892 was created. Another entity called the International Association of Chemical Societies (IACS) exis ...
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Di-tert-butoxyacetylene
Di-''tert''-butoxyacetylene is the organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ... with the formula (CH3)3COC≡COC(CH3)3. It is a pale yellow liquid. It is one of the more common dialkoxyacetylenes; most other dialkoxyacetylenes are very labile, for example, dimethoxyacetylene polymerizes within seconds at 0 °C. Di-''tert''-butoxyacetylene can be prepared from 1,4-dioxane in a multistep procedure.{{cite journal , first1=Anna, last1=Bou, first2=Miquel A. , last2=Pericàs, first3=Antoni, last3=Riera, first4=Fèlix, last4=Serratosa, doi=10.15227/orgsyn.065.0068, title=Dialkoxyacetylenes: Di-''tert''-butoxyethyne, A Valuable Synthetic Intermediate, journal=Organic Syntheses, year=1987, volume=65, page=68 References Tert-butyl compounds Alkyne derivatives ...
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Organic Synthesis
Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the general subject of organic synthesis, there are many different types of synthetic routes that can be completed including total synthesis, Enantioselective synthesis, stereoselective synthesis, automated synthesis, and many more. Additionally, in understanding organic synthesis it is necessary to be familiar with the methodology, techniques, and applications of the subject. Total synthesis A total synthesis refers to the complete chemical synthesis of molecules from simple, Precursor (chemistry), natural precursors. Total synthesis is accomplished either via a linear or convergent approach. In a Linear synthesis, ''linear'' synthesis—often adequate for simple structures—several steps are performed sequentially until the molecule is com ...
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Enol Ether
In organic chemistry an enol ether is an alkene with an alkoxy substituent. The general structure is R2C=CR-OR where R = H, alkyl or aryl. A common subfamily of enol ethers are vinyl ethers, with the formula ROCH=CH2. Important enol ethers include the reagent 3,4-dihydropyran and the monomers methyl vinyl ether and ethyl vinyl ether. Reactions and uses Akin to enamines, enol ethers are electron-rich alkenes by virtue of the electron-donation from the heteroatom via pi-bonding. Enol ethers have oxonium ion character. By virtue of their bonding situation, enol ethers display distinctive reactivity. In comparison with simple alkenes, enol ethers exhibit enhanced susceptibility to attack by electrophiles such as Bronsted acids. Similarly, they undergo inverse demand Diels-Alder reactions. The reactivity of enol ethers is highly dependent on the presence of substituents alpha to oxygen. The vinyl ethers are susceptible to polymerization to give polyvinyl ethers. They also re ...
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Dimethoxyethane
Dimethoxyethane, also known as glyme, monoglyme, dimethyl glycol, ethylene glycol dimethyl ether, dimethyl cellosolve, and DME, is a colorless, aprotic, and liquid ether that is used as a solvent, especially in batteries. Dimethoxyethane is miscible with water. Production Monoglyme is produced industrially by the reaction of dimethylether with ethylene oxide: :CH3OCH3 + CH2CH2O → CH3OCH2CH2OCH3 Applications as solvent and ligand left, 144px, Structure of the coordination complex NbCl3(dimethoxyethane)(3-hexyne). Together with a high-permittivity solvent (e.g. propylene carbonate), dimethoxyethane is used as the low-viscosity component of the solvent for electrolytes of lithium batteries. In the laboratory, DME is used as a coordinating solvent. Dimethoxyethane is often used as a higher-boiling-point alternative to diethyl ether and tetrahydrofuran. Dimethoxyethane acts as a bidentate ligand for some metal cations. It is therefore often used in organometallic chemist ...
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Anisole
Anisole, or methoxybenzene, is an organic compound with the formula . It is a colorless liquid with a smell reminiscent of anise seed, and in fact many of its derivatives are found in natural and artificial fragrances. The compound is mainly made synthetically and is a precursor to other synthetic compounds. Structurally, it is an ether () with a methyl () and phenyl () group attached. Anisole is a standard reagent of both practical and pedagogical value. Reactivity Anisole undergoes electrophilic aromatic substitution reaction at a faster speed than benzene, which in turn reacts more quickly than nitrobenzene. The methoxy group is an ortho/para directing group, which means that electrophilic substitution preferentially occurs at these three sites. The enhanced nucleophilicity of anisole vs. benzene reflects the influence of the methoxy group, which renders the ring more electron-rich. The methoxy group strongly affects the pi cloud of the ring as a mesomeric electron ...
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Dipropyl Ether
Dipropyl ether is the symmetrical ether of two ''n''-propyl groups. It is a colorless, flammable liquid with a sweet odor typical of ethers. Preparation Acid catalyzed ether synthesis Dipropyl ether can be synthesized by reacting two molecules of 1-Propanol, ''n''-propanol in the presence of p-toluenesulfonic acid (a strong acid) and heat, in the same way other symmetrical ethers may be formed. Williamson ether synthesis This ether may also be prepared by way of the Williamson ether synthesis in which ''n''-propoxide, the conjugate base of ''n''-propanol, is reacted with an ''n''-propyl halide: : Safety As is typical of ethers, dipropyl ether may slowly form explosive organic peroxides over long periods in storage. Antioxidants such as butylated hydroxytoluene are often added to ethers to prevent this process. Due to the shock and light sensitive nature of organic peroxides, dipropyl ether should never be boiled or evaporated to dryness. This concentrates peroxides that ma ...
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