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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:
In transhydrocyanation, an equivalent of HCN is transferred from a cyanohydrin, e.g. acetone cyanohydrin, to another HCN acceptor. The transfer is an equilibrium process, initiated by base. The reaction can be driven by trapping reactions or by the use of a superior HCN acceptor, such as an aldehyde. [6]
In organic chemistry, a cyanohydrin reaction is an organic reaction in which an aldehyde (−CH=O) or ketone (>C=O) reacts with a cyanide anion ...
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 ...
Another synthetic pathway for α-hydroxy acids involves the addition of hydrogen cyanide to ketones or aldehydes, followed by the acidic hydrolysis of the cyanohydrin intermediate. [14] R−CHO + HCN → R−CH(OH)CN R−CH(OH)CN + 2H 2 O → R−CH(OH)CO 2 H + NH 3
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