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Organofluorine compounds are prepared by numerous routes, depending on the degree and regiochemistry of fluorination sought and the nature of the precursors. The direct fluorination of hydrocarbons with F 2, often diluted with N 2, is useful for highly fluorinated compounds: R 3 CH + F 2 → R 3 CF + HF
The well-characterized heavier halogens (chlorine, bromine, and iodine) all form mono-, tri-, and pentafluorides: XF, XF 3, and XF 5. Of the neutral +7 species, only iodine heptafluoride is known. [93] While chlorine and bromine heptafluorides are not known, the corresponding cations ClF + 6 and BrF + 6, extremely strong oxidizers, are. [94]
A common preparative method involves fluorination of sodium hydroxide: 2 F 2 + 2 NaOH → OF 2 + 2 NaF + H 2 O. OF 2 is a colorless gas at room temperature and a yellow liquid below 128 K. Oxygen difluoride has an irritating odor and is poisonous. [3] It reacts quantitatively with aqueous haloacids to give free halogens: OF 2 + 4 HCl → 2 Cl 2 ...
Such reagents include cobalt trifluoride, chlorine trifluoride, and iodine pentafluoride. [4] The method electrochemical fluorination is used commercially for the production of perfluorinated compounds. It generates small amounts of elemental fluorine in situ from hydrogen fluoride. The method avoids the hazards of handling fluorine gas.
Chlorine pentafluoride (ClF 5) is made on a large scale by direct fluorination of chlorine with excess fluorine gas at 350 °C and 250 atm, and on a small scale by reacting metal chlorides with fluorine gas at 100–300 °C. It melts at −103 °C and boils at −13.1 °C.
Organic redox reactions: the Birch reduction. Organic reductions or organic oxidations or organic redox reactions are redox reactions that take place with organic compounds.In organic chemistry oxidations and reductions are different from ordinary redox reactions, because many reactions carry the name but do not actually involve electron transfer. [1]
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.
Perchloryl fluoride is produced primarily by the fluorination of perchlorates. The initial syntheses in the early 1950s used fluorine gas or fluorides and anodic oxidation as the fluorinating agents, but these give explosive gaseous mixtures. [8] A common fluorinator in modern syntheses is antimony pentafluoride: [3]: 372–373 ClO − 4 + 3 HF ...