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Halogenation of benzene where X is the halogen, catalyst represents the catalyst (if needed) and HX represents the protonated base. A few types of aromatic compounds, such as phenol , will react without a catalyst , but for typical benzene derivatives with less reactive substrates, a Lewis acid is required as a catalyst .
In chemistry, halogenation is a chemical reaction which introduces one or more halogens into a chemical compound. Halide-containing compounds are pervasive, making this type of transformation important, e.g. in the production of polymers, drugs. [1] This kind of conversion is in fact so common that a comprehensive overview is challenging.
In biochemistry, naturally occurring phenols are natural products containing at least one phenol functional group. [1] [2] [3] Phenolic compounds are produced by plants and microorganisms. [4] Organisms sometimes synthesize phenolic compounds in response to ecological pressures such as pathogen and insect attack, UV radiation and wounding. [5]
Halogenations of organic compounds by free halogens (F 2, Cl 2, Br 2, and sometimes I 2) is generally favorable process. It is practiced industrially on a large scale for example. In nature, however, free halogens do not exist in appreciable amounts.
The overall reaction mechanism, denoted by the Hughes–Ingold mechanistic symbol S E Ar, [3] begins with the aromatic ring attacking the electrophile E + (2a). This step leads to the formation of a positively charged and delocalized cyclohexadienyl cation, also known as an arenium ion, Wheland intermediate, or arene σ-complex (2b).
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The most commonly employed Sandmeyer reactions are the chlorination, bromination, cyanation, and hydroxylation reactions using CuCl, CuBr, CuCN, and Cu 2 O, respectively. More recently, trifluoromethylation of diazonium salts has been developed and is referred to as a 'Sandmeyer-type' reaction.