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Halogenation of saturated hydrocarbons is a substitution reaction. The reaction typically involves free radical pathways. The regiochemistry of the halogenation of alkanes is largely determined by the relative weakness of the C–H bonds. This trend is reflected by the faster reaction at tertiary and secondary positions.
Inhaled agents like diethyl ether are critical in anesthesia. Diethyl ether initially replaced non-flammable (but more toxic) halogenated hydrocarbons like chloroform and trichloroethylene. Halothane is a halogenated hydrocarbon anesthetic agent that was introduced into clinical practice in 1956. Due to its ease of use and improved safety ...
Regiochemistry follows from the reaction mechanism, which exhibits halogen attack on the least-hindered unsaturated carbon. The mechanism for this chain reaction resembles free radical halogenation, in which the peroxide promotes formation of the bromine radical. However, this process is restricted to addition of HBr.
Free radical halogenation reactions occur with halogens, leading to the production of haloalkanes. The hydrogen atoms of the alkane are progressively replaced by halogen atoms. The reaction of alkanes and fluorine is highly exothermic and can lead to an explosion. [29] These reactions are an important industrial route to halogenated hydrocarbons.
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 UV light. The reaction is used for the industrial synthesis of chloroform (CHCl 3), dichloromethane (CH 2 Cl 2), and hexachlorobutadiene. It proceeds by a free-radical chain ...
Alkanes react with halogens by free radical halogenation. In this reaction a hydrogen atom is removed from the alkane, then replaced by a halogen atom by reaction with a diatomic halogen molecule. Free radical halogenation typically produces a mixture of compounds mono- or multihalogenated at various positions. [citation needed]
A good example of a substitution reaction is halogenation. When chlorine gas (Cl 2) is irradiated, some of the molecules are split into two chlorine radicals (Cl•), whose free electrons are strongly nucleophilic. One of them breaks a C–H covalent bond in CH 4 and grabs the hydrogen atom to form the electrically neutral HCl.
In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. [1]: ... Halogenation. Saturated hydrocarbons react with ...