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Cycloaddition
In organic chemistry, a cycloaddition is a chemical reaction in which "two or more unsaturated molecules (or parts of the same molecule) combine with the formation of a cyclic adduct in which there is a net reduction of the bond multiplicity". The resulting reaction is a cyclization reaction. Many but not all cycloadditions are concerted and thus pericyclic. Nonconcerted cycloadditions are not pericyclic. As a class of addition reaction, cycloadditions permit carbon–carbon bond formation without the use of a nucleophile or electrophile. Cycloadditions can be described using two systems of notation. An older but still common notation is based on the size of linear arrangements of atoms in the reactants. It uses parentheses: where the variables are the numbers of linear atoms in each reactant. The product is a cycle of size . In this system, the standard Diels-Alder reaction is a (4 + 2)-cycloaddition, the 1,3-dipolar cycloaddition is a (3 + 2)-cy ...
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Chemical Reaction
A chemical reaction is a process that leads to the 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 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 elements where both electronic and nuclear changes can occur. The substance (or substances) initially involved in a chemical reaction are called reactants or reagents. Chemical reactions are usually characterized by a chemical change, and they yield one or more products, which usually have properties different from the reactants. Reactions often consist of a sequence of individual sub-steps, the so-called elementary reactions, and the information on the precise course ...
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Allenes
In organic chemistry, allenes are organic compounds in which one carbon atom has double bonds with each of its two adjacent carbon centres (). Allenes are classified as cumulated dienes. The parent compound of this class is propadiene, which is itself also called ''allene''. Compounds with an allene-type structure but with more than three carbon atoms are members of a larger class of compounds called cumulenes with bonding. History For many years, allenes were viewed as curiosities but thought to be synthetically useless and difficult to prepare and to work with.The Chemistry of the Allenes (vol. 1−3); Landor, S. R., Ed.; cademic Press: London, 1982. Reportedly, the first synthesis of an allene, glutinic acid, was performed in an attempt to prove the non-existence of this class of compounds. The situation began to change in the 1950s, and more than 300 papers on allenes have been published in 2012 alone. These compounds are not just interesting intermediates but syntheti ...
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Ketene
In organic chemistry, a ketene is an organic compound of the form , where R and R' are two arbitrary monovalent chemical groups (or two separate substitution sites in the same molecule). The name may also refer to the specific compound ethenone , the simplest ketene. Although they are highly useful, most ketenes are unstable. When used as reagents in a chemical procedure, they are typically generated when needed, and consumed as soon as (or while) they are produced. History Ketenes were first studied as a class by Hermann Staudinger before 1905. Ketenes were systematically investigated by Hermann Staudinger in 1905 in the form of diphenylketene (conversion of \alpha-chlorodiphenyl acetyl chloride with zinc). Staudinger was inspired by the first examples of reactive organic intermediates and stable radicals discovered by Moses Gomberg in 1900 (compounds with triphenylmethyl group). Properties Ketenes are highly electrophilic at the carbon atom bonded with the heteroatom, ...
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Pericyclic
In organic chemistry, a pericyclic reaction is the type of organic reaction wherein the transition state of the molecule has a cyclic geometry, the reaction progresses in a concerted fashion, and the bond orbitals involved in the reaction overlap in a continuous cycle at the transition state. Pericyclic reactions stand in contrast to ''linear reactions'', encompassing most organic transformations and proceeding through an acyclic transition state, on the one hand and '' coarctate reactions'', which proceed through a doubly cyclic, concerted transition state on the other hand. Pericyclic reactions are usually rearrangement or addition reactions. The major classes of pericyclic reactions are given in the table below (the three most important classes are shown in bold). Ene reactions and cheletropic reactions are often classed as group transfer reactions and cycloadditions/cycloeliminations, respectively, while dyotropic reactions and group transfer reactions (if ene reactions are ...
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Photochemistry
Photochemistry is the branch of chemistry concerned with the chemical effects of light. Generally, this term is used to describe a chemical reaction caused by absorption of ultraviolet ( wavelength from 100 to 400  nm), visible light (400–750 nm) or infrared radiation (750–2500 nm). In nature, photochemistry is of immense importance as it is the basis of photosynthesis, vision, and the formation of vitamin D with sunlight. Photochemical reactions proceed differently than temperature-driven reactions. Photochemical paths access high energy intermediates that cannot be generated thermally, thereby overcoming large activation barriers in a short period of time, and allowing reactions otherwise inaccessible by thermal processes. Photochemistry can also be destructive, as illustrated by the photodegradation of plastics. Concept Grotthuss–Draper law and Stark-Einstein law Photoexcitation is the first step in a photochemical process where the reactant is elev ...
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Unsaturated Hydrocarbon
300px, Structure of an ethene molecule, the simplest unsaturated hydrocarbon Unsaturated hydrocarbons are hydrocarbons that have double or triple covalent bonds between adjacent carbon atoms. The term "unsaturated" means more hydrogen atoms may be added to the hydrocarbon to make it saturated (i.e. consisting all single bonds). The configuration of an unsaturated carbons include straight chain, such as alkenes and alkynes, as well as branched chains and aromatic compounds. Except for aromatic compounds, unsaturated hydrocarbons are mostly reactive and undergo multiple reactions to their multiple bonds. Nomenclature For the sake of clearer communication and less misunderstanding, a consistent naming system is necessary, which gives rise to the IUPAC nomenclature. Some standard steps to follow when naming unsaturated hydrocarbon molecules with IUPAC nomenclature are elaborated below. *1. Find and count the number of carbon atoms in the longest carbon chain and use the cor ...
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Cyclopropanation
In organic chemistry, cyclopropanation refers to any chemical process which generates cyclopropane () rings. It is an important process in modern chemistry as many useful compounds bear this motif; for example pyrethroids and a number of quinolone antibiotics (ciprofloxacin, sparfloxacin, etc.). However, the high ring strain present in cyclopropanes makes them challenging to produce and generally requires the use of highly reactive species, such as carbenes, ylids and carbanions. Many of the reactions proceed in a cheletropic manner. Approaches From alkenes using carbenoid reagents Several methods exist for converting alkenes to cyclopropane rings using carbene type reagents. As carbenes themselves are highly reactive it is common for them to be used in a stabilised form, referred to as a carbenoid. Simmons–Smith reaction In the Simmons–Smith reaction the reactive carbenoid is iodomethylzinc iodide, which is typically formed by a reaction between diiodomethane and a ...
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Suprafacial
Antarafacial ( Woodward-Hoffmann symbol a) and suprafacial (s) are two topological concepts in organic chemistry describing the relationship between two simultaneous chemical bond making and/or bond breaking processes in or around a reaction center. The reaction center can be a p- or sp''n-''orbital (Woodward-Hoffmann symbol ω), a conjugated system (π) or even a sigma bond (σ). * The relationship is ''antarafacial'' when opposite faces of the π system or isolated orbital are involved in the process (think ''anti''). For a σ bond, it corresponds to involvement of one "interior" lobe and one "exterior" lobe of the bond. * The relationship is ''suprafacial'' when the same face of the π system or isolated orbital are involved in the process (think ''syn''). For a σ bond, it corresponds to involvement of two "interior" lobes or two "exterior" lobes of the bond. The components of all pericyclic reactions, including sigmatropic reactions and cycloadditions, and electrocyclizatio ...
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Cyclization
A cyclic compound (or ring compound) is a term for a compound in the field of chemistry in which one or more series of atoms in the compound is connected to form a ring. Rings may vary in size from three to many atoms, and include examples where all the atoms are carbon (i.e., are carbocycles), none of the atoms are carbon (inorganic cyclic compounds), or where both carbon and non-carbon atoms are present (heterocyclic compounds). Depending on the ring size, the bond order of the individual links between ring atoms, and their arrangements within the rings, carbocyclic and heterocyclic compounds may be aromatic or non-aromatic; in the latter case, they may vary from being fully saturated to having varying numbers of multiple bonds between the ring atoms. Because of the tremendous diversity allowed, in combination, by the valences of common atoms and their ability to form rings, the number of possible cyclic structures, even of small size (e.g., < 17 total atoms) numbers in the ma ...
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Addition Reaction
In organic chemistry, an addition reaction is, in simplest terms, an organic reaction where two or more molecules combine to form a larger one (the adduct).. Addition reactions are limited to chemical compounds that have multiple bonds, such as molecules with carbon–carbon double bonds (alkenes), or with triple bonds (alkynes), and compounds that have rings, which are also considered points of unsaturation. Molecules containing carbon— hetero double bonds like carbonyl () groups, or imine () groups, can undergo addition, as they too have double-bond character. An addition reaction is the reverse of an elimination reaction. For instance, the hydration of an alkene to an alcohol is reversed by dehydration. There are two main types of polar addition reactions: electrophilic addition and nucleophilic addition. Two non-polar addition reactions exist as well, called free-radical addition and cycloadditions. Addition reactions are also encountered in polymerizations and call ...
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Antarafacial
Antarafacial ( Woodward-Hoffmann symbol a) and suprafacial (s) are two topological concepts in organic chemistry describing the relationship between two simultaneous chemical bond making and/or bond breaking processes in or around a reaction center. The reaction center can be a p- or sp''n-''orbital (Woodward-Hoffmann symbol ω), a conjugated system (π) or even a sigma bond (σ). * The relationship is ''antarafacial'' when opposite faces of the π system or isolated orbital are involved in the process (think ''anti''). For a σ bond, it corresponds to involvement of one "interior" lobe and one "exterior" lobe of the bond. * The relationship is ''suprafacial'' when the same face of the π system or isolated orbital are involved in the process (think ''syn''). For a σ bond, it corresponds to involvement of two "interior" lobes or two "exterior" lobes of the bond. The components of all pericyclic reactions, including sigmatropic reactions and cycloadditions, and electrocycliza ...
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