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Cyanohydrin
 
 
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A cyanohydrin is a functional group
Functional group

In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules....
 found in organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
s. Cyanohydrins have the formula R2C(OH)CN, where R is H, alkyl
Alkyl

An alkyl is a univalent Radical consisting of carbon and hydrogen atoms, arranged in a chain. The Alkyls form homologous series with the general formula CnH2n+1....
, or aryl
Aryl

In the context of organic molecules, aryl refers to any functional group or substituent derived from a simple aromatic ring, may it be phenyl, thiophene, indole, etc ....
. Cyanohydrins are industrially important precursors to carboxylic acid
Carboxylic acid

Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the Chemical formula -COH, usually written -COOH or -CO2H....
s and some amino acid
Amino acid

In chemistry, an amino acid is a molecule containing both amine and carboxyl functional groups. These molecules are particularly important in biochemistry, where this term refers to alpha-amino acids with the general formula H2NCHRCOOH, where R is an organic substituent....
s. Cyanohydrins can be formed by the cyanohydrin reaction
Cyanohydrin reaction

A Cyanohydrin reaction is an organic reaction by an aldehyde or ketone with a cyanide anion or a nitrile to form a cyanohydrin. This nucleophilic addition is a reversible reaction but with aliphatic carbonyl compounds equilibrium is in favor of the reaction products....
, which involves treating a ketone
Ketone

In organic chemistry, a ketone is a type of organic compound which contains a carbonyl group bonded to two other carbon atoms in the form:Neither of the substituents R1 and R2 may be equal to hydrogen ....
 or an aldehyde
Aldehyde

An aldehyde is an organic compound containing a terminal carbonyl group. This functional group, which consists of a carbon atom bonded to a hydrogen atom and double bond to an oxygen atom , is called the aldehyde group....
 with hydrogen cyanide
Hydrogen cyanide

Hydrogen cyanide is a chemical compound with chemical formula HCN. A solution of hydrogen cyanide in water is called hydrocyanic acid. Hydrogen cyanide is a colorless, extremely poisonous, and highly volatility liquid that boiling slightly above room temperature at 26 Celsius ....
 (HCN) in the presence of excess amounts of sodium cyanide
Sodium cyanide

Sodium cyanide is the inorganic compound with the chemical formula NaCN. This highly toxic colourless salt is used mainly in gold mining but has other niche applications....
 (NaCN) as a catalyst:

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.






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Encyclopedia


A cyanohydrin is a functional group
Functional group

In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules....
 found in organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
s. Cyanohydrins have the formula R2C(OH)CN, where R is H, alkyl
Alkyl

An alkyl is a univalent Radical consisting of carbon and hydrogen atoms, arranged in a chain. The Alkyls form homologous series with the general formula CnH2n+1....
, or aryl
Aryl

In the context of organic molecules, aryl refers to any functional group or substituent derived from a simple aromatic ring, may it be phenyl, thiophene, indole, etc ....
. Cyanohydrins are industrially important precursors to carboxylic acid
Carboxylic acid

Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the Chemical formula -COH, usually written -COOH or -CO2H....
s and some amino acid
Amino acid

In chemistry, an amino acid is a molecule containing both amine and carboxyl functional groups. These molecules are particularly important in biochemistry, where this term refers to alpha-amino acids with the general formula H2NCHRCOOH, where R is an organic substituent....
s. Cyanohydrins can be formed by the cyanohydrin reaction
Cyanohydrin reaction

A Cyanohydrin reaction is an organic reaction by an aldehyde or ketone with a cyanide anion or a nitrile to form a cyanohydrin. This nucleophilic addition is a reversible reaction but with aliphatic carbonyl compounds equilibrium is in favor of the reaction products....
, which involves treating a ketone
Ketone

In organic chemistry, a ketone is a type of organic compound which contains a carbonyl group bonded to two other carbon atoms in the form:Neither of the substituents R1 and R2 may be equal to hydrogen ....
 or an aldehyde
Aldehyde

An aldehyde is an organic compound containing a terminal carbonyl group. This functional group, which consists of a carbon atom bonded to a hydrogen atom and double bond to an oxygen atom , is called the aldehyde group....
 with hydrogen cyanide
Hydrogen cyanide

Hydrogen cyanide is a chemical compound with chemical formula HCN. A solution of hydrogen cyanide in water is called hydrocyanic acid. Hydrogen cyanide is a colorless, extremely poisonous, and highly volatility liquid that boiling slightly above room temperature at 26 Celsius ....
 (HCN) in the presence of excess amounts of sodium cyanide
Sodium cyanide

Sodium cyanide is the inorganic compound with the chemical formula NaCN. This highly toxic colourless salt is used mainly in gold mining but has other niche applications....
 (NaCN) as a catalyst:

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
Sulfite

Sulfites are chemical compound that contain the sulfite ion sulfuroxygen32- ....
 by cyanide salts:

Cyanohydrins are intermediates in the Strecker amino acid synthesis
Strecker amino acid synthesis

The Strecker amino acid synthesis, devised by Adolph Strecker, is a series of chemical reactions that synthesize an amino acid from an aldehyde ....
.

Acetone cyanohydrins

Acetone cyanohydrin
Acetone cyanohydrin

Acetone cyanohydrin is an organic compound used in the production of methyl methacrylate, the monomer of the transparent plastic polymethyl methacrylate , also known as acrylic....
, (CH3)2C(OH)CN is the cyanohydrin of acetone
Acetone

Acetone is the organic compound with the chemical formula OC2. This colorless, mobile, flammable liquid is the simplest example of the ketones....
. It is generated as an intermediate in the industrial production of methyl methacrylate
Methyl methacrylate

Methyl methacrylate is an organic compound with the chemical formula CH2=CCO2CH3. This colourless liquid, the methyl ester of methacrylic acid is a monomer produced on a large scale for the production of polymethyl methacrylate ....
. In the laboratory, this liquid serves as a source of HCN, which is inconveniently volatile. Thus, acetone cyanohydrin can be used for the preparation other cyanohydrins, for of HCN to Michael acceptors, and for the formylation
Gattermann-Koch reaction

The Gattermann-Koch reaction, named for the German chemists Ludwig Gattermann and Julius Arnold Koch, in organic chemistry refers to a Friedel-Crafts acylation reaction in which carbon monoxide and hydrochloric acid are used in-situ with Friedel-Crafts catalyst, namely AlCl3 to produce a benzaldehyde-derivative from a benzene-deriv...
 of arene
Arene

Arene or Ar?n? or Ar?ne may refer to:*an aromatic hydrocarbon*Arene , the wife of Aphareus and mother of Idas and Lynceus in Greek mythology...
s. Treatment of this cyanohydrin with lithium hydride
Lithium hydride

Lithium hydride is the chemical compound of lithium and hydrogen. It is a colourless crystalline solid, although commercial samples appear gray....
 affords anhydrous
Anhydrous

As a general term, a substance is said to be anhydrous if it contains no water. The way of achieving the anhydrous form differs from one substance to another....
 lithium cyanide:


Other cyanohydrins

Mandelonitrile
Mandelonitrile

Mandelonitrile is a chemical compound of the cyanohydrin class. Small amounts of mandelonitrile occur in the Drupe of some fruits....
, with the formula C6H5CH
Benzyl

In organic chemistry, benzyl is the term used to describe the substituent or molecular fragment possessing the structure C6H5CH2-....
(OH)CN, occurs in small amounts in the pits of some fruits. Related cyanogenic glycosides are known, such as amygdalin
Amygdalin

Amygdalin , C20H27NO11, is a glycoside initially isolated from the seeds of the tree Prunus dulcis, also known as bitter almonds, by Pierre-Jean Robiquet...
.

Glycolonitrile, also called hydroxyacetonitrile or formaldehyde cyanohydrin (CAS#107-16-4), is the organic compound with the formula HOCH2CN. It is the simplest cyanohydrin, being derived from formaldehyde
Formaldehyde

Formaldehyde is a chemical compound with the chemical formula H2CO. It is the simplest aldehyde. Formaldehyde exists in several forms aside from H2CO: the cyclic trimer trioxane and the polymer Polyoxymethylene....
.

glycolonitrile
acetone cyanohydrin
mandelonitrile


External links

  • IUPACs Gold Book
    Gold Book

    Compendium of Chemical Terminology is a book published by IUPAC containing internationally accepted definitions for terms in chemistry. Work on the first edition was initiated by Victor Gold, hence its informal name, the Gold Book....
     definition of cyanohydrins