The Wohl degradation in carbohydrate chemistry is a chain contraction method for

aldose An aldose is a monosaccharide (a simple sugar) with a carbon backbone chain with a carbonyl group on the endmost carbon atom, making it an aldehyde, and hydroxyl groups connected to all the other carbon atoms. Aldoses can be distinguished from ket ...

s. The classic example is the conversion of

glucose Glucose is a sugar with the Chemical formula#Molecular formula, molecular formula , which is often abbreviated as Glc. It is overall the most abundant monosaccharide, a subcategory of carbohydrates. It is mainly made by plants and most algae d ...

to arabinose as shown below. The reaction is named after the German chemist Alfred Wohl (1863–1939). Let's say we have a kiliani-fischer synthesis, it basically removes the row of the C2 carbon, it shortens the carbon chain by one carbon. In one modification, d-glucose is converted to the glucose

oxime In organic chemistry, an oxime is an organic compound belonging to the imines, with the general Chemical formula, formula , where R is an organic Side chain, side-chain and R' may be hydrogen, forming an aldoxime, or another organic functional g ...

by reaction with hydroxylamine and

sodium methoxide Sodium methoxide is the simplest sodium alkoxide. With the formula , it is a white solid, which is formed by the deprotonation of methanol. It is a widely used reagent in industry and the laboratory. It is also a dangerously caustic base. ...

. In the second step the is formed by reaction with

acetic anhydride Acetic anhydride, or ethanoic anhydride, is the chemical compound with the chemical formula, formula . Commonly abbreviated , it is one the simplest organic acid anhydride, anhydrides of a carboxylic acid and is widely used in the production of c ...

acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main compone ...

with

sodium acetate Sodium acetate, CH3COONa, also abbreviated Sodium, NaOxygen, OAcetyl, Ac, is the sodium Salt (chemistry), salt of acetic acid. This salt is colorless, deliquescent, and hygroscopy, hygroscopic. Applications Biotechnological Sodium acetate is u ...

. In this reaction step the oxime is converted into the

nitrile In organic chemistry, a nitrile is any organic compound that has a functional group. The name of the compound is composed of a base, which includes the carbon of the , suffixed with "nitrile", so for example is called " propionitrile" (or pr ...

with simultaneous conversion of all the

alcohol Alcohol may refer to: Common uses * Alcohol (chemistry), a class of compounds * Ethanol, one of several alcohols, commonly known as alcohol in everyday life ** Alcohol (drug), intoxicant found in alcoholic beverages ** Alcoholic beverage, an alco ...

groups to

acetate An acetate is a salt formed by the combination of acetic acid with a base (e.g. alkaline, earthy, metallic, nonmetallic, or radical base). "Acetate" also describes the conjugate base or ion (specifically, the negatively charged ion called ...

groups. In the final step

methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical compound and the simplest aliphatic Alcohol (chemistry), alcohol, with the chemical formula (a methyl group linked to a hydroxyl group, often ab ...

is added, leading to removal of all the acetate groups and ejection of the nitrile group and collapse of the second carbon from a tetrahedral structure to an aldehyde.

Ruff–Fenton degradation

In a variation, the Ruff–Fenton degradation ( Otto Ruff 1898, H.J.H. Fenton 1893) converts the aldose first to the alpha-hydroxy-carboxylic acid with

bromine Bromine is a chemical element; it has chemical symbol, symbol Br and atomic number 35. It is a volatile red-brown liquid at room temperature that evaporates readily to form a similarly coloured vapour. Its properties are intermediate between th ...

and

calcium hydroxide Calcium hydroxide (traditionally called slaked lime) is an inorganic compound with the chemical formula Ca( OH)2. It is a colorless crystal or white powder and is produced when quicklime ( calcium oxide) is mixed with water. Annually, approxim ...

and then to the shortened aldose by reaction with

Iron(III) sulfate Iron(III) sulfate or ferric sulfate (British English: sulphate instead of sulfate) is a family of inorganic compounds with the formula Fe2(SO4)3(H2O)n. A variety of hydrates are known, including the most commonly encountered form of "ferric sulf ...

and

hydrogen peroxide Hydrogen peroxide is a chemical compound with the formula . In its pure form, it is a very pale blue liquid that is slightly more viscosity, viscous than Properties of water, water. It is used as an oxidizer, bleaching agent, and antiseptic, usua ...

.''Organic syntheses based on name reactions'', Volume 22 Alfred Hassner, C. Stumer

References

{{Organic reactions Carbohydrate chemistry Elimination reactions Degradation reactions Name reactions

Ruff–Fenton degradation

See also

References