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In the laboratory, this liquid serves as a source of HCN, which is inconveniently volatile. [4] Thus, acetone cyanohydrin can be used for the preparation of other cyanohydrins, for the transformation of HCN to Michael acceptors, and for the formylation of arenes. Treatment of this cyanohydrin with lithium hydride affords anhydrous lithium cyanide:
It is used as a surrogate in place of HCN, as illustrated by its use as a precursor to lithium cyanide: [8] (CH 3) 2 C(OH)CN + LiH → (CH 3) 2 CO + LiCN + H 2. In transhydrocyanation, an equivalent of HCN is transferred from acetone cyanohydrin to another acceptor, with acetone as byproduct. The transfer is an equilibrium process, initiated by ...
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The Kiliani–Fischer synthesis, named for German chemists Heinrich Kiliani and Emil Fischer, is a method for synthesizing monosaccharides.It proceeds via synthesis and hydrolysis of a cyanohydrin, followed by reduction of the intermediate acid to the aldehyde, thus elongating the carbon chain of an aldose by one carbon atom while preserving stereochemistry on all the previously present chiral ...
HCN is produced on an industrial scale and is a highly valued precursor to many chemical compounds ranging from polymers to pharmaceuticals. Large-scale applications are for the production of potassium cyanide and adiponitrile, used in mining and plastics, respectively. [10] It is more toxic than solid cyanide compounds due to its volatile nature.
The chemist Urech in 1872 was the first to synthesize cyanohydrins from ketones with alkali cyanides and acetic acid [2] and therefore this reaction also goes by the name of Urech cyanohydrin method. References
The cyanohydrins and aldehydes used for the synthesis are usually aromatic, however there have been instances where aliphatic compounds have been used. The first step of the mechanism is the addition of gaseous HCl to the cyanohydrin 1. The cyanohydrin abstracts the hydrogen from HCl while the chloride ion attacks the carbon in the cyano group.
LiCN is produced from the reaction of lithium hydroxide and hydrogen cyanide. A laboratory-scale preparation uses acetone cyanohydrin as a surrogate for HCN: [5] (CH 3) 2 C(OH)CN + LiH → (CH 3) 2 CO + LiCN + H 2