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Acyl halide

In chemistry Chemistry

Chemistry is the science [i] of matter [i] at the atom [i]ic to molecular [i] scale, dealing primarily ... 

, the term acyl halide refers to a compound derived from an acid by replacing a hydroxyl group with a halide group. If the acid is a carboxylic acid Carboxylic acid

Carboxylic acids are organic acid [i]s characterized by the presence of a carboxyl group, which ha ... 

, the compound contains a -COX functional group Functional group

In organic chemistry [i] functional groups are specific groups of atom [i]s within molecule [i]s, that ... 

, which consists of a carbonyl group Carbonyl

In organic chemistry [i], a carbonyl group is a functional group [i] composed of a carbon [i] atom [i] double-bonded [i] ... 

 singly bonded to a halogen Halogen

The halogens are a chemical series [i]. ... 

 atom such as chlorine. The general formula for such an acyl halide can be written RCOX, where R may be, for example, an alkyl Alkyl

An alkyl is a univalent [i] radical [i] containing only carbon [i] and hydrogen [i] atoms arrang ... 

 group, CO is the carbonyl group, and X represents the halogen atom. See simple diagram at right. The RCO- group in an acyl halide can be thought of as an acyl group and the -X radical as the halide part of the molecule; for example, -Cl is chloride.

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In chemistry Chemistry

Chemistry is the science [i] of matter [i] at the atom [i]ic to molecular [i] scale, dealing primarily ... 

, the term acyl halide refers to a compound derived from an acid by replacing a hydroxyl group with a halide group.

If the acid is a carboxylic acid Carboxylic acid

Carboxylic acids are organic acid [i]s characterized by the presence of a carboxyl group, which ha ... 

, the compound contains a -COX functional group Functional group

In organic chemistry [i] functional groups are specific groups of atom [i]s within molecule [i]s, that ... 

, which consists of a carbonyl group Carbonyl

In organic chemistry [i], a carbonyl group is a functional group [i] composed of a carbon [i] atom [i] double-bonded [i]... 

 singly bonded to a halogen Halogen

The halogens are a chemical series [i]. ... 

 atom such as chlorine. The general formula for such an acyl halide can be written RCOX, where R may be, for example, an alkyl Alkyl

An alkyl is a univalent [i] radical [i] containing only carbon [i] and hydrogen [i] atoms arrang ... 

 group, CO is the carbonyl group, and X represents the halogen atom. See simple diagram at right.

The RCO- group in an acyl halide can be thought of as an acyl group and the -X radical as the halide part of the molecule; for example, -Cl is chloride. Acyl chlorides Acyl chloride

In organic chemistry [i], an acyl chloride is an organic compound [i] which is a reactive derivative of ... 

 are the most commonly used acyl halides. Acyl halides are commonly made by halogenating a carboxylic acid, hence the name acid halide.

An example of an acyl halide is acetyl chloride Acetyl chloride

Acetyl chloride, also known as ethanoyl chloride, is an acid chloride [i] derived from acetic acid [i] ... 

 CH3COCl. See simple diagram at right.

Another example is replacing hydroxyl by chloride in a sulfonic acid Sulfonic acid

Sulfonic acid is an hypothetical acid [i] with formula H-S(=O)2-OH. ... 

 to create a sulfonyl chloride Sulfonic acid

Sulfonic acid is an hypothetical acid [i] with formula H-S(=O)2-OH. ... 

.

Acyl halide synthesis

A common method for the synthesis of acyl halides in the laboratory is by reaction of carboxylic acid Carboxylic acid

Carboxylic acids are organic acid [i]s characterized by the presence of a carboxyl group, which ha ... 

s with reagents such as thionyl chloride Thionyl chloride

Thionyl chloride is an inorganic compound [i] with the formula [i] S [i]O [i] ... 

 and phosphorus pentachloride Phosphorus chlorides

Several phosphorus chlorides are known.... 

 for acyl halides, phosphorus tribromide Phosphorus tribromide

| Phosphorus tribromide
|-
| align="center" colspan="2" |
... 

 for acyl bromides and cyanuric fluoride Cyanuric acid

Cyanuric acid or 1,3,5-triazine-2,4,6-triol is an organic chemical compound [i] with the chemical formula [i] ... 

 for acyl fluorides

Acyl halide reactions

Acyl halides are artificial , rather reactive compounds often synthesized to be used as intermediates in the synthesis of other organic compounds. For example, an acyl halide can chemically react Chemical reaction

A chemical reaction is a process that results in the interconversion of chemical substance [i]s . ... 

 with:
  • water Water

    Water is a taste [i]less, odor [i]less substance that is essential to all known forms of life [i] and i ... 

     to form a carboxylic acid Carboxylic acid

    Carboxylic acids are organic acid [i]s characterized by the presence of a carboxyl group, which ha ... 




  • an alcohol Alcohol

    In chemistry [i], an alcohol is any organic compound [i] in which a hydroxyl [i] group [i] ... 

     to form an ester Ester

    In chemistry [i], esters are organic compound [i]s in which an organic group [i] replac ... 




  • an amine Amine

    Amines are organic compound [i]s and a type of functional group [i] that contain nitrogen [i] as the key ... 

     to form an amide Amide

    n chemistry [i], an amide is one of two kinds of compound [i]s:

... 



  • an aromatic compound, using a catalyst such as AlCl3, to form an aromatic ketone Ketone

    A ketone is either the functional group [i] characterized by a carbonyl [i] group linked to two other carbon [i]... 

    . See Friedel-Crafts acylation Friedel-Crafts reaction

    [i] developed by [[Charles Friedel]... 

    .


In the above reactions, HX is also formed. For example, if the acyl halide is an acyl chloride, HCl is also formed.

Because acyl halides are rather reactive compounds, they have toxicity Toxicity

Toxicity is a measure to the degree to which something is toxic or poison [i]ous. ... 

 and special precautions should be taken handling them. They are lachrymatory chemicals 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.

Multiple functional groups



A molecule can have more than one acyl halide functional group. For example, "adipoyl dichloride", usually simply called adipoyl chloride Adipoyl chloride

Adipoyl chloride is a di-acyl chloride [i], with formula C6H8Cl2O2.
... 

, has two acyl chloride functional group Functional group

In organic chemistry [i] functional groups are specific groups of atom [i]s within molecule [i]s, that ... 

s; see the structure at right. It is the dichloride of the 6-carbon dicarboxylic acid adipic acid Adipic acid

Adipic acid is a chemical compound [i] of the class of carboxylic acid [i]s. ... 

. An important use of adipoyl chloride is polymerization with an organic di-amino compound to form a polyamide called nylon Nylon

Nylon [i] represents a family of synthetic polymer [i]s, a thermoplastic [i] material, fir ... 

 or polymerization with certain other organic compounds to form polyester Polyester

Polyester is a category of polymer [i]s, or, more specifically condensation polymer [i]s, which contain ... 

s.

Phosgene Phosgene

Phosgene is the chemical compound [i] with the formula COCl2. ... 

  is a very toxic gas which may be thought of as the dichloride of carbonic acid Carbonic acid

Carbonic acid is the only inorganic [i] carbon [i] acid [i], and has the formula [i]... 

 . 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 Polycarbonate

h colspan="2" align=center bgcolor="#cccccc">Polycarbonate
... 

 polymers, among other industrial applications.

See also

  • organic chemistry Organic chemistry

    Organic chemistry is a specific discipline within the subject of chemistry [i]. ... 



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