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Halogenation

 

 
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Halogenation
 
 
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"Fluorination" redirects here. For the addition of fluoride to drinking water, see water fluoridation
Water fluoridation

Water fluoridation is the controlled addition of fluoride to a public water supply to reduce tooth decay. Fluoridated water has fluoride at a level that is effective for preventing cavities; this can occur naturally or by adding fluoride....
.


Halogenation is a chemical reaction
Chemical reaction

A chemical reaction is a process that always results in the interconversion of chemical substances. The substance or substances initially involved in a chemical reaction are called reactants....
 that incorporates a halogen
Halogen

|}The halogens or halogen elements are a chemical series of nonmetal chemical element from Periodic table group International Union of Pure and Applied Chemistry of the periodic table, comprising fluorine, F; chlorine, Cl; bromine, Br; iodine, I; and astatine, At....
 atom into a molecule. More specific descriptions exist that specify the type of halogen: fluorination, chlorination, bromination, and iodination.

In a Markovnikov addition
Markovnikov's rule

In organic chemistry, Markovnikov's rule or Markownikoff's rule is an observation based on Zaitsev's rule. It was formulated by the Russian chemist Vladimir Vasilevich Markovnikov in 1870 ....
 reaction, a halogen like bromine
Bromine

Bromine , , meaning "stench " ), is a chemical element with the symbol Br and atomic number 35. A halogen element, bromine is a reddish-brown Volatility liquid at Standard conditions for temperature and pressure that is intermediate in reactivity between chlorine and iodine....
 is reacted with an alkene
Alkene

In organic chemistry, an alkene, olefin, or olefine is an Saturation chemical compound containing at least one carbon-to-carbon double bond....
 which causes the p-bond
Pi bond

In chemistry, pi bonds are covalent bond chemical bonds where two lobes of one involved electron atomic orbital overlap two lobes of the other involved electron orbital....
 to break forming an haloalkane
Haloalkane

The haloalkanes are a group of chemical compounds, consisting of alkanes, such as methane or ethane, with one or more halogens linked, such as chlorine or fluorine, making them a type of organic halide....
.






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Encyclopedia


"Fluorination" redirects here. For the addition of fluoride to drinking water, see water fluoridation
Water fluoridation

Water fluoridation is the controlled addition of fluoride to a public water supply to reduce tooth decay. Fluoridated water has fluoride at a level that is effective for preventing cavities; this can occur naturally or by adding fluoride....
.


Halogenation is a chemical reaction
Chemical reaction

A chemical reaction is a process that always results in the interconversion of chemical substances. The substance or substances initially involved in a chemical reaction are called reactants....
 that incorporates a halogen
Halogen

|}The halogens or halogen elements are a chemical series of nonmetal chemical element from Periodic table group International Union of Pure and Applied Chemistry of the periodic table, comprising fluorine, F; chlorine, Cl; bromine, Br; iodine, I; and astatine, At....
 atom into a molecule. More specific descriptions exist that specify the type of halogen: fluorination, chlorination, bromination, and iodination.

In a Markovnikov addition
Markovnikov's rule

In organic chemistry, Markovnikov's rule or Markownikoff's rule is an observation based on Zaitsev's rule. It was formulated by the Russian chemist Vladimir Vasilevich Markovnikov in 1870 ....
 reaction, a halogen like bromine
Bromine

Bromine , , meaning "stench " ), is a chemical element with the symbol Br and atomic number 35. A halogen element, bromine is a reddish-brown Volatility liquid at Standard conditions for temperature and pressure that is intermediate in reactivity between chlorine and iodine....
 is reacted with an alkene
Alkene

In organic chemistry, an alkene, olefin, or olefine is an Saturation chemical compound containing at least one carbon-to-carbon double bond....
 which causes the p-bond
Pi bond

In chemistry, pi bonds are covalent bond chemical bonds where two lobes of one involved electron atomic orbital overlap two lobes of the other involved electron orbital....
 to break forming an haloalkane
Haloalkane

The haloalkanes are a group of chemical compounds, consisting of alkanes, such as methane or ethane, with one or more halogens linked, such as chlorine or fluorine, making them a type of organic halide....
. This makes the hydrocarbon
Hydrocarbon

In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. With relation to chemical terminology, aromatic hydrocarbons or arenes, alkanes, alkenes and alkyne-based compounds composed entirely of carbon or hydrogen are referred to as "pure" hydrocarbons, whereas other hydrocarbons with bonded com...
 more reactive and bromine
Bromine

Bromine , , meaning "stench " ), is a chemical element with the symbol Br and atomic number 35. A halogen element, bromine is a reddish-brown Volatility liquid at Standard conditions for temperature and pressure that is intermediate in reactivity between chlorine and iodine....
 as it turns out, is a good leaving group
Leaving group

A leaving group in chemistry is an ion or substituent with the ability to detach itself from a molecule. The remaining molecule or fragment remaining is known as the residual or main part....
 in further chemical reactions such as nucleophilic aliphatic substitution reactions and elimination reaction
Elimination reaction

An elimination reaction is a type of organic reaction in which two substituents are removed from a molecule in either a one or two-step mechanism ....
s.

Several main types of halogenation exist, including:

  • Free radical halogenation
    Free radical halogenation

    In organic chemistry, free radical halogenation is a type of halogenation. This chemical reaction is typical of alkanes and alkyl-substituted aromatics under application of heat or UV light....
  • Ketone halogenation
    Ketone halogenation

    In organic chemistry ketone halogenation is a special type of halogenation.The position alpha to the carbonyl group in a ketone is easily halogenated, due to the ability to form an enolate anion in basic solution, or an enol in acidic solution....
  • Electrophilic halogenation
    Electrophilic halogenation

    In organic chemistry, an electrophilic aromatic halogenation is a type of electrophilic aromatic substitution. This organic reaction is typical of aromatic compounds and a very useful method for adding substituents to an aromatic system....
  • Halogen addition reaction
    Halogen addition reaction

    A halogen addition reaction is a simple organic reaction where a halogen molecule is added to the carbon-carbon double bond of an alkene functional group ....


Examples


The formation of Gold(III) chloride
Gold(III) chloride

Gold chloride, traditionally called auric chloride, is the chemical inorganic compound with the formula GoldChloride3. The Roman numerals in the name indicate that the gold has an oxidation state of +3, which is common for gold in its compounds....
 by the chlorination
Chlorination

Chlorination is the process of adding the element chlorine to water as a method of water purification to make it fit for human consumption as drinking water....
 of gold
Gold

Gold is a chemical element with the symbol Au and atomic number 79. It is a highly sought-after precious metal, having been used as money, as a store of value, in jewelry, in sculpture, and for ornamentation since the beginning of recorded history....
.

Specific halogenation methods are the Hunsdiecker reaction
Hunsdiecker reaction

The Hunsdiecker reaction is the organic reaction of silver salts of carboxylic acids with halogens to give organic halides. It is an example of a halogenation reaction....
 (from carboxylic acids) and the Sandmeyer reaction
Sandmeyer reaction

The Sandmeyer reaction is a chemical reaction used to synthesize aryl halides from aryl diazonium salts. It is named after the Swiss chemist Traugott Sandmeyer....
 (arylhalides).

An example of halogenation can be found in the organic synthesis
Organic synthesis

Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic_chemistry molecules can often contain a higher level of complexity compared to purely Inorganic_chemistry compounds, so the synthesis of organic compounds has developed into one of the most im...
 of the anesthetic halothane
Halothane

Halothane vapour is an inhalational general anaesthetic. Its IUPAC name is 2-bromo-2-chloro-1,1,1-trifluoroethane. It is the only inhalational anaesthetic agent containing a bromine atom; there are several other halogenated anesthesia agents which lack the bromine atom and do contain the fluorine and chlorine atoms present in halothane....
 from trichloroethylene
Trichloroethylene

The chemical compound trichloroethylene is a chlorine hydrocarbon commonly used as an industrial solvent. It is a clear non-flammable liquid with a sweet smell....
 which involves a high temperature bromination in the second step :

Halothane Synthesis

See also

  • Haloalkane
    Haloalkane

    The haloalkanes are a group of chemical compounds, consisting of alkanes, such as methane or ethane, with one or more halogens linked, such as chlorine or fluorine, making them a type of organic halide....
     (Alkyl halide)
  • Halogenoarene
    Halogenoarene

    In organic chemistry, a halogenoarene, haloarene, or aryl halide, is an organic compound in which a halogen atom is bonded to a carbon atom which is part of an aromatic ring....
     (Aryl halide)
  • Free radical halogenation
    Free radical halogenation

    In organic chemistry, free radical halogenation is a type of halogenation. This chemical reaction is typical of alkanes and alkyl-substituted aromatics under application of heat or UV light....
  • Haloketone
    Haloketone

    A haloketone in organic chemistry is a functional group consisting of a ketone group or more general a carbonyl group with a a-halogen substituent....
  • Electrophilic substitution
    Electrophilic substitution

    Electrophilic substitution reactions are chemical reactions in which an electrophile displaces another group, typically but not always hydrogen....