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Encyclopedia > Acyl halide
Acyl Halide
Acyl Halide

An acyl halide (also known as an acid halide) is a chemical compound derived from an acid by replacing a hydroxyl group with a halide group.[1] Image File history File links No higher resolution available. ... A chemical compound is a chemical substance of two or more different chemically bonded chemical elements, with a fixed ratio determining the composition. ... Acidity redirects here. ... // Hydroxyl group The term hydroxyl group is used to describe the functional group -OH when it is a substituent in an organic compound. ... A halide is a binary compound, of which one part is a halogen atom and the other part is an element or radical that is less electronegative than the halogen, to make a fluoride, chloride, bromide, iodide, or astatide compound. ...


If the acid is a carboxylic acid, the compound contains a –COX functional group, which consists of a carbonyl group singly bonded to a halogen atom. The general formula for such an acyl halide can be written RCOX, where R may be, for example, an alkyl group, CO is the carbonyl group, and X represents the halogen atom, e.g. chlorine: acyl chlorides are the most commonly used acyl halides. Structure of a carboxylic acid The 3D structure of the carboxyl group A space-filling model of the carboxyl group Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)OH, usually written -COOH or -CO2H. [1] Carboxylic acids are Bronsted... In organic chemistry, functional groups (or moieties) are specific groups of atoms within molecules, that are responsible for the characteristic chemical reactions of those molecules. ... In chemistry, a carbonyl group is a functional group composed of an atom of carbon double-bonded to an atom of oxygen. ... The halogens or halogen elements are a series of nonmetal elements from Group 17 (old-style: VII or VIIA; Group 7 IUPAC Style) of the periodic table, comprising fluorine, F, chlorine, Cl, bromine, Br, iodine, I, and astatine, At. ... An alkyl is a univalent radical containing only carbon and hydrogen atoms arranged in a chain. ... General Name, Symbol, Number chlorine, Cl, 17 Chemical series halogens Group, Period, Block 17, 3, p Appearance yellowish green Standard atomic weight 35. ... General Chemical Structure of an Acyl Chloride In organic chemistry, an acyl chloride (or acid chloride) is an organic compound which is a reactive derivative of a carboxylic acid. ...

The hydroxyl group of a sulfonic acid may also be replaced by a halogen to produce the corresponding sulfonyl halide. In practical terms this is almost always chlorine to create a sulfonyl chloride. Wikipedia does not have an article with this exact name. ... It has been suggested that Sulfonic acid/Temp be merged into this article or section. ... Thionyl chloride (or thionyl dichloride) is an inorganic compound with the formula SOCl2. ...

Contents

Preparation

A common method for the synthesis of acyl halides in the laboratory is by reaction of carboxylic acids with reagents such as thionyl chloride or phosphorus pentachloride for acyl chlorides, phosphorus tribromide for acyl bromides and cyanuric fluoride for acyl fluorides. Structure of a carboxylic acid The 3D structure of the carboxyl group A space-filling model of the carboxyl group Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)OH, usually written -COOH or -CO2H. [1] Carboxylic acids are Bronsted... R-phrases , , , S-phrases , , , Flash point non flammable Supplementary data page Structure and properties n, εr, etc. ... Phosphorus pentachloride is the chemical compound with the formula PCl5. ... Phosphorus tribromide is a colourless liquid with the formula PBr3. ... A cyanogen halide is a molecule consisting of cyanide and a halogen. ...


Aromatic acyl chlorides can be prepared by chloroformylation, a specific type of Friedal-Crafts acylation using formaldehyde as the reagent. The term aromatic compound may also refer to: any organic compound possessing a strong olfactory aroma aromatic hydrocarbons (originally named as a subset of the above; however, aromatic hydrocarbons do not necessarily possess any smell whatsoever) ... The Friedel-Crafts reactions are a set of reactions developed by Charles Friedel and James Crafts in 1877. ... The chemical compound formaldehyde (also known as methanal) is a gas with a pungent smell. ...


Reactions

Acyl halides are rather reactive compounds often synthesized to be used as intermediates in the synthesis of other organic compounds. For example, an acyl halide can react with: Vapours of hydrogen chloride in a beaker and ammonia in a test tube meet to form a cloud of a new substance, ammonium chloride A chemical reaction is a process that results in the interconversion of chemical substances. ...

Image:Hydration_of_Acyl_Halide.PNG This article describes water from a scientific and technical perspective. ... Structure of a carboxylic acid The 3D structure of the carboxyl group A space-filling model of the carboxyl group Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)OH, usually written -COOH or -CO2H. [1] Carboxylic acids are Bronsted... Image File history File links No higher resolution available. ...

Image:Acyl_Halide_plus_Alcohol.PNG This article does not cite any references or sources. ... A carboxylic acid ester. ... Image File history File links No higher resolution available. ...

Image:Acyl_Halide_plus_Amine.PNG The general structure of an amine Amines are organic compounds and a type of functional group that contain nitrogen as the key atom. ... Amide functional group Amides possess a conjugated system spread over the O, C and N atoms, consisting of molecular orbitals occupied by delocalized electrons. ... Image File history File links No higher resolution available. ...

In the above reactions, HX (hydrogen halide or hydrohalic acid) is also formed. For example, if the acyl halide is an acyl chloride, HCl (hydrogen chloride or hydrochloric acid) is also formed. The term aromatic compound may also refer to: any organic compound possessing a strong olfactory aroma aromatic hydrocarbons (originally named as a subset of the above; however, aromatic hydrocarbons do not necessarily possess any smell whatsoever) ... In chemistry, a Lewis acid can accept a pair of electrons and form a coordinate covalent bond, after the American chemist Gilbert Lewis. ... Ketone group A ketone(key tone) is either the functional group characterized by a carbonyl group (O=C) linked to two other carbon atoms or a chemical compound that contains this functional group. ... The Friedel-Crafts reactions were developed by Charles Friedel and James Crafts in 1877. ... It has been suggested that this article or section be merged with Hydrohalic acid. ... R-phrases , S-phrases , , , , Flash point non-flammable Supplementary data page Structure and properties n, εr, etc. ... The chemical compound hydrochloric acid is the aqueous (water-based) solution of hydrogen chloride gas (HCl). ...


Multiple functional groups

Adipoyl chloride
Adipoyl chloride

A molecule can have more than one acyl halide functional group. For example, "adipoyl dichloride", usually simply called adipoyl chloride, has two acyl chloride functional groups; see the structure at right. It is the dichloride (i.e., double chloride) of the 6-carbon dicarboxylic acid adipic acid. An important use of adipoyl chloride is polymerization with an organic di-amino compound to form a polyamide called nylon or polymerization with certain other organic compounds to form polyesters. Image File history File links No higher resolution available. ... Image File history File links No higher resolution available. ... Adipoyl chloride (or adipoyl dichloride) is an acyl chloride, with formula C6H8Cl2O2. ... In organic chemistry, functional groups (or moieties) are specific groups of atoms within molecules, that are responsible for the characteristic chemical reactions of those molecules. ... Adipic acid is the common name of 1,6-hexanedioic acid, a chemical compound of the class of carboxylic acids. ... An example of alkene polymerisation, in which each Styrene monomer units double bond reforms as a single bond with another styrene monomer and forms polystyrene. ... Nylon is a generic designation for a family of synthetic polymers first produced on February 28, 1935 by Wallace Carothers at DuPont. ... SEM picture of a bend in a high surface area polyester fiber with a seven-lobed cross section Polyester is a category of polymers, or, more specifically condensation polymers, which contain the ester functional group in their main chain. ...


Phosgene (carbonyl dichloride, Cl–CO–Cl) is a very toxic gas which may be thought of as the dichloride of carbonic acid (HO–CO–OH). Both chloride radicals in phosgene can undergo reactions analogous to the preceding reactions of acyl halides. Phosgene is used a reactant in the production of polycarbonate polymers, among other industrial applications. Phosgene is a highly toxic chemical compound with the formula COCl2. ... Carbonic acid (ancient name acid of air or aerial acid) has the formula H2CO3. ... Polycarbonates are a particular group of thermoplastic polyesters. ...


General hazards

Volatile acyl halides are lachrymatory because they can react with water at the surface of the eye producing hydrohalic and organic acids irritating to the eye. Similar problems can result if one inhales acyl halide vapors. In general, acyl halides (even non-volatile compounds such as tosyl chloride) are irritants to the eyes, skin and mucous membranes. Categories: Stub | Chemical weapons ... The tosylate group with a generic R group attached Ball-and-stick model of the tosylate anion A tosyl group (abbreviated Ts or Tos) combines the toluene and sulfonyl functional groups. ... The word irritant may refer to: Something that causes irritation, often a chemical substance. ... The mucous membranes (or mucosae; singular: mucosa) are linings of mostly endodermal origin, covered in epithelium, and are involved in absorption and secretion. ...


References

  1. ^ International Union of Pure and Applied Chemistry. "acyl halides". Compendium of Chemical Terminology Internet edition.

  Results from FactBites:
 
Acyl halide - Wikipedia, the free encyclopedia (408 words)
An acyl halide (also known as an acid halide) is an organic compound containing a -COX functional group, which consists of a carbonyl group singly bonded to a halogen atom such as chlorine ( Cl ).
Acyl halides are commonly made by halogenating a carboxylic acid, hence the name acid halide.
Acyl halides are artificial, rather reactive compounds often synthesized to be used as intermediates in the synthesis of other organic compounds.
  More results at FactBites »

 
 

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