In organic chemistry, a cyanohydrin or hydroxynitrile is a functional group found in organic compounds in which a cyano and a hydroxy group are attached to the same carbon atom. The general formula is R2C(OH)CN, where R is H, alkyl, or aryl. Cyanohydrins are industrially important precursors to carboxylic acids and some amino acids. Cyanohydrins can be formed by the cyanohydrin reaction, which involves treating a ketone or an aldehyde with hydrogen cyanide (HCN) in the presence of excess amounts of sodium cyanide (NaCN) as a catalyst:[1]
RR’C=O + HCN → RR’C(OH)CN
In this reaction, the nucleophilic CN− ion attacks the electrophilic carbonyl carbon in the ketone, followed by protonation by HCN, thereby regenerating the cyanide anion. Cyanohydrins are also prepared by displacement of sulfite by cyanide salts:[2]
Cyanohydrins are intermediates in the Strecker amino acid synthesis. In aqueous acid, they are hydrolyzed to the α-hydroxy acid.
^David T. Mowry (1948). "The Preparation of Nitriles". Chem. Rev.42 (2): 189–283. doi:10.1021/cr60132a001. PMID 18914000.
^Corson, B. B.; Dodge, R. A.; Harris, S. A.; Yeaw, J. S. (1941). "Mandelic Acid". Organic Syntheses; Collected Volumes, vol. 1, p. 336.
In organic chemistry, a cyanohydrin or hydroxynitrile is a functional group found in organic compounds in which a cyano and a hydroxy group are attached...
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a cyanohydrin and an aldehyde in the presence of anhydrous hydrochloric acid. This method was discovered by Emil Fischer in 1896. The cyanohydrin itself...
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For example, in the cyanohydrin reaction a cyanide ion forms a C-C bond by breaking the carbonyl's double bond to form a cyanohydrin. With nitrile electrophiles...
(−CH3). Although nitriles generally do not release cyanide ions, the cyanohydrins do and are thus toxic. The cyanide ion −C≡N is isoelectronic with carbon...
in use, include hydrogenation of oxalic acid, and hydrolysis of the cyanohydrin derived from formaldehyde. Some of today's glycolic acids are formic...
The cyanohydrins are a special class of nitriles. Classically they result from the addition of alkali metal cyanides to aldehydes in the cyanohydrin reaction...
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Top 0–9 A B C D E F G H I J K L M N O P Q R S T U V W X Y Z Acetone cyanohydrin Acetone thiosemicarbazide Acrolein Acrylamide Acrylonitrile Acryloyl...
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the glucoside of methyl ethyl ketone cyanohydrin and is structurally related to linamarin, the acetone cyanohydrin glucoside also found in these plants...
cyanide to ketones or aldehydes, followed by the acidic hydrolysis of the cyanohydrin intermediate. R−CHO + HCN → R−CH(OH)CN R−CH(OH)CN + 2H2O → R−CH(OH)CO2H...
the industrial production of ethyl lactate and lactic acid. It is the cyanohydrin of acetaldehyde. It is a colorless liquid, although degraded samples...
and formaldehyde. The resulting hydroxypivaldehyde is converted to its cyanohydrin derivative. which is cyclised to give racemic pantolactone. This sequence...
and for the electroplating of those metals. Via the intermediacy of cyanohydrins, a variety of useful organic compounds are prepared from HCN including...
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