Jacobsen Rearrangement
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Jacobsen Rearrangement
The Jacobsen rearrangement is a chemical reaction, commonly described as the migration of an alkyl group in a sulfonic acid derived from a polyalkyl- or polyhalobenzene: The exact reaction mechanism is not completely clear, but evidence indicates that the rearrangement occurs intermolecularly and that the migrating group is transferred to a polyalkylbenzene, not to the sulfonic acid ( sulfonation only takes place ''after'' migration). The intermolecular mechanism is partially illustrated by the side products found in the following example: Furthermore, the reaction is limited to benzene rings with at least four substituents (alkyl and/or halogen groups). The sulfo group is easily removed, so the Jacobsen rearrangement can also be considered as a rearrangement of polyalkylbenzenes. It was Herzig who described this type of rearrangement for the first time in 1881 using polyhalogenated benzenesulfonic acids, but the reaction took the name of the German chemist Oscar Jacobsen ...
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Chemical Reaction
A chemical reaction is a process that leads to the IUPAC nomenclature for organic transformations, chemical transformation of one set of chemical substances to another. Classically, chemical reactions encompass changes that only involve the positions of electrons in the forming and breaking of chemical bonds between atoms, with no change to the Atomic nucleus, nuclei (no change to the elements present), and can often be described by a chemical equation. Nuclear chemistry is a sub-discipline of chemistry that involves the chemical reactions of unstable and radioactive Chemical element, elements where both electronic and nuclear changes can occur. The substance (or substances) initially involved in a chemical reaction are called reagent, reactants or reagents. Chemical reactions are usually characterized by a chemical change, and they yield one or more Product (chemistry), products, which usually have properties different from the reactants. Reactions often consist of a sequence o ...
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Alkyl
In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term ''alkyl'' is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl is derived from a cycloalkane by removal of a hydrogen atom from a Ring (chemistry), ring and has the general formula . Typically an alkyl is a part of a larger molecule. In structural formulae, the symbol R is used to designate a generic (unspecified) alkyl group. The smallest alkyl group is methyl, with the formula . Related concepts Alkylation is an important operation in refineries, for example in the production of high-octane gasoline. Alkylating antineoplastic agents are a class of compounds that are used to treat cancer. In such case, the term alkyl is used loosely. For example, nitrogen mustards are well-known alkylating agents, but they are not simple hydrocarbons. In chemistry, alkyl is a group, a substituent, that is attached to other molecular fr ...
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Sulfonic Acid
In organic chemistry, sulfonic acid (or sulphonic acid) refers to a member of the class of organosulfur compounds with the general formula , where R is an organic alkyl or aryl group and the group a sulfonyl hydroxide. As a substituent, it is known as a sulfo group. A sulfonic acid can be thought of as sulfuric acid with one hydroxyl group replaced by an organic substituent. The parent compound (with the organic substituent replaced by hydrogen) is the parent sulfonic acid, , a tautomer of sulfurous acid, . Salt (chemistry), Salts or esters of sulfonic acids are called sulfonates. Preparation Aryl sulfonic acids are produced by the process of sulfonation. Usually the sulfonating agent is sulfur trioxide. A large scale application of this method is the production of alkylbenzenesulfonic acids: :RC6H5 + SO3 -> RC6H4SO3H In this reaction, sulfur trioxide is an electrophile and the arene is the nucleophile. The reaction is an example of electrophilic aromatic substitution. Alkyl ...
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Jacobsen
Jacobsen may refer to: * Jacobsen (surname), including a list of people with the name * Jacobsen Manufacturing, a former American manufacturer ** Jacobsen, a brand of lawn-care products by Textron * Jacobsen Publishing, publisher of several American regional newspapers * Jacobsen (beer), a brand of specialty beers owned by Carlsberg * Miranda, California (formerly Jacobsen's), a place in Humboldt County, California, U.S. See also * Jacobson (other) * Jakobsen, a surname * Jakobson (surname) * Theodor Jacobsen Observatory The Theodor Jacobsen Observatory is the on-campus observatory of the University of Washington. Built in 1895, it is the second oldest building on campus and was constructed using the remaining Tenino, Washington, Tenino sandstone blocks from De ..., University of Washington, U.S. * H. N. Jacobsens Bókahandil, a bookshop in Tórshavn, Faroe Islands {{disambig ...
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Intermolecular
An intermolecular force (IMF) (or secondary force) is the force that mediates interaction between molecules, including the electromagnetic forces of attraction or repulsion which act between atoms and other types of neighbouring particles, e.g. atoms or ions. Intermolecular forces are weak relative to intramolecular forces – the forces which hold a molecule together. For example, the covalent bond, involving sharing electron pairs between atoms, is much stronger than the forces present between neighboring molecules. Both sets of forces are essential parts of force fields frequently used in molecular mechanics. The investigation of intermolecular forces starts from macroscopic observations which indicate the existence and action of forces at a molecular level. These observations include non-ideal-gas thermodynamic behavior reflected by virial coefficients, vapor pressure, viscosity, superficial tension, and absorption data. The first reference to the nature of microscopic forc ...
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Sulfonation
Aromatic sulfonation is an organic reaction in which a hydrogen atom on an arene is replaced by a sulfonic acid functional group in an electrophilic aromatic substitution. Aryl sulfonic acids are used as detergents, dye, and drugs. Stoichiometry and mechanism Typical conditions involve heating the aromatic compound with sulfuric acid: :C6H6 + H2SO4 → C6H5SO3H + H2O Sulfur trioxide or its protonated derivative is the actual electrophile in this electrophilic aromatic substitution. To drive the equilibrium, dehydrating agents such as thionyl chloride can be added. :C6H6 + H2SO4 + SOCl2 → C6H5SO3H + SO2 + 2 HCl Chlorosulfuric acid is also an effective agent: :C6H6 + HSO3Cl → C6H5SO3H + HCl In contrast to aromatic nitration and most other electrophilic aromatic substitutions this reaction is reversible. Sulfonation takes place in concentrated acidic conditions and desulfonation is the mode of action in a dilute hot aqueous acid. The reaction is very useful in protecting the a ...
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Jacobsen2
Jacobsen may refer to: * Jacobsen (surname), including a list of people with the name * Jacobsen Manufacturing, a former American manufacturer ** Jacobsen, a brand of lawn-care products by Textron * Jacobsen Publishing, publisher of several American regional newspapers * Jacobsen (beer), a brand of specialty beers owned by Carlsberg * Miranda, California (formerly Jacobsen's), a place in Humboldt County, California, U.S. See also * Jacobson (other) * Jakobsen, a surname * Jakobson (surname) * Theodor Jacobsen Observatory The Theodor Jacobsen Observatory is the on-campus observatory of the University of Washington. Built in 1895, it is the second oldest building on campus and was constructed using the remaining Tenino, Washington, Tenino sandstone blocks from De ..., University of Washington, U.S. * H. N. Jacobsens Bókahandil, a bookshop in Tórshavn, Faroe Islands {{disambig ...
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Chemical Reaction
A chemical reaction is a process that leads to the IUPAC nomenclature for organic transformations, chemical transformation of one set of chemical substances to another. Classically, chemical reactions encompass changes that only involve the positions of electrons in the forming and breaking of chemical bonds between atoms, with no change to the Atomic nucleus, nuclei (no change to the elements present), and can often be described by a chemical equation. Nuclear chemistry is a sub-discipline of chemistry that involves the chemical reactions of unstable and radioactive Chemical element, elements where both electronic and nuclear changes can occur. The substance (or substances) initially involved in a chemical reaction are called reagent, reactants or reagents. Chemical reactions are usually characterized by a chemical change, and they yield one or more Product (chemistry), products, which usually have properties different from the reactants. Reactions often consist of a sequence o ...
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Arene
Aromatic compounds, also known as "mono- and polycyclic aromatic hydrocarbons", are organic compounds containing one or more aromatic rings. The parent member of aromatic compounds is benzene. The word "aromatic" originates from the past grouping of molecules based on smell, before their general chemical properties are understood. The current definition of aromatic compounds does not have any relation with their smell. Heteroarenes are closely related, since at least one carbon atom of CH group is replaced by one of the heteroatoms oxygen, nitrogen, or sulfur. Examples of non-benzene compounds with aromatic properties are furan, a heterocyclic compound with a five-membered ring that includes a single oxygen atom, and pyridine, a heterocyclic compound with a six-membered ring containing one nitrogen atom. Hydrocarbons without an aromatic ring are called aliphatic. Benzene ring model Benzene, C6H6, is the least complex aromatic hydrocarbon, and it was the first one named as such ...
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Substituent
A substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. (In organic chemistry and biochemistry, the terms ''substituent'' and ''functional group'', as well as ''side chain'' and '' pendant group'', are used almost interchangeably to describe those branches from the parent structure, though certain distinctions are made in polymer chemistry. In polymers, side chains extend from the backbone structure. In proteins, side chains are attached to the alpha carbon atoms of the amino acid backbone.) The suffix ''-yl'' is used when naming organic compounds that contain a single bond replacing one hydrogen; ''-ylidene'' and ''-ylidyne'' are used with double bonds and triple bonds, respectively. In addition, when naming hydrocarbons that contain a substituent, positional numbers are used to indicate which carbon atom the substituent attaches to when such information is needed to distinguish between isomers. Su ...
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Halogen
The halogens () are a group in the periodic table consisting of five or six chemically related elements: fluorine (F), chlorine (Cl), bromine (Br), iodine (I), astatine (At), and tennessine (Ts). In the modern IUPAC nomenclature, this group is known as group 17. The word "halogen" means "salt former" (or "salt maker"). When halogens react with metals, they produce a wide range of salts, including calcium fluoride, sodium chloride (common table salt), silver bromide and potassium iodide. The group of halogens is the only periodic table group that contains elements in three of the main states of matter at standard temperature and pressure. All of the halogens form acids when bonded to hydrogen. Most halogens are typically produced from minerals or salts. The middle halogens—chlorine, bromine, and iodine—are often used as disinfectants. Organobromides are the most important class of flame retardants, while elemental halogens are dangerous and can be toxic. History The fl ...
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