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Thionyl chloride is an inorganic compound with the chemical formula SOCl 2.It is a moderately volatile, colourless liquid with an unpleasant acrid odour.Thionyl chloride is primarily used as a chlorinating reagent, with approximately 45,000 tonnes (50,000 short tons) per year being produced during the early 1990s, [5] but is occasionally also used as a solvent.
Oxalyl chloride reacts with water giving off gaseous products only: hydrogen chloride (HCl), carbon dioxide (CO 2), and carbon monoxide (CO). (COCl) 2 + H 2 O → 2 HCl + CO 2 + CO In this, it is quite different from other acyl chlorides which hydrolyze with formation of hydrogen chloride and the original carboxylic acid.
In the Arndt-Eistert homologation reaction, a carboxylic acid and thionyl chloride are reacted to generate an acid chloride. The acid chloride then reacts with diazomethane (R 2 = H), or occasionally a diazoalkyl, via the Arndt-Eistert procedure, to generate an α-diazo ketone, which will undergo a metal-catalyzed or photolyzed Wolff ...
Some derivatives of formic acid, like formyl chloride (−COCl), undergo spontaneous decarbonylation at room temperature (or below). Reactions involving oxalyl chloride (COCl) 2 (e.g., hydrolysis, reaction with carboxylic acids, Swern oxidation, etc.) often liberate both carbon dioxide and carbon monoxide via a fragmentation process.
In organic chemistry, the Arndt–Eistert reaction is the conversion of a carboxylic acid to its homologue. It is named for the German chemists Fritz Arndt (1885–1969) and Bernd Eistert (1902–1978). The method entails treating an acid chlorides with diazomethane. It is a popular method of producing β-amino acids from α-amino acids. [1]
This reaction mechanism is supported by the observation that addition of pyridine to the reaction leads to inversion. The reasoning behind this finding is that pyridine reacts with the intermediate sulfite replacing chlorine. The dislodged chlorine has to resort to nucleophilic attack from the rear as in a regular nucleophilic substitution. [3]
In organic chemistry, the Swern oxidation, named after Daniel Swern, is a chemical reaction whereby a primary or secondary alcohol (−OH) is oxidized to an aldehyde (−CH=O) or ketone (>C=O) using oxalyl chloride, dimethyl sulfoxide (DMSO) and an organic base, such as triethylamine.
Acid chlorides are useful for the preparation of amides, esters, anhydrides. These reactions generate chloride, which can be undesirable.Acyl chlorides are used to prepare acid anhydrides, amides and esters, by reacting acid chlorides with: a salt of a carboxylic acid, an amine, or an alcohol, respectively.