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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 ...
A free-radical reaction is any chemical reaction involving free radicals.This reaction type is abundant in organic reactions.Two pioneering studies into free radical reactions have been the discovery of the triphenylmethyl radical by Moses Gomberg (1900) and the lead-mirror experiment [1] described by Friedrich Paneth in 1927.
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. Free radical chlorination is used for the industrial production of some solvents: [2]
Radical reaction mechanisms use single-headed arrows to depict the movement of single electrons: Example of an arrow-pushing mechanism for an internal radical reaction. The homolytic cleavage of the breaking bond is drawn with a "fish-hook" arrow to distinguish from the usual movement of two electrons depicted by a standard curly arrow. The ...
Benzal chloride is produced by the free radical chlorination of toluene, being preceded in the process by benzyl chloride (C 6 H 5 CH 2 Cl) and followed by benzotrichloride (C 6 H 5 CCl 3):
Chlorine, for example, gives two chlorine radicals (Cl•) by irradiation with ultraviolet light. This process is used for chlorination of alkanes . Azo compounds (R- N =N-R') can be the precursor of two carbon -centered radicals (R• and R'•) and nitrogen gas upon heating and/or by irradiation.
The reaction occurs via a free radical mechanism. UV-light initiates homolysis of chlorine, producing a pair of chlorine atoms: . Chain initiation: Thereafter a chlorine atom attacks the hydrocarbon chain, freeing hydrogen to form hydrogen chloride and an alkyl free radical.
A hydrohalogenation reaction is the electrophilic addition of hydrogen halides like hydrogen chloride or hydrogen bromide to alkenes to yield the corresponding haloalkanes. [ 1 ] [ 2 ] [ 3 ] If the two carbon atoms at the double bond are linked to a different number of hydrogen atoms, the halogen is found preferentially at the carbon with fewer ...