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In organic chemistry, Fehling's solution is a chemical reagent used to differentiate between water-soluble carbohydrate and ketone (>C=O) functional groups, and as a test for reducing sugars and non-reducing sugars, supplementary to the Tollens' reagent test. The test was developed by German chemist Hermann von Fehling in 1849. [1]
Alpha-hydroxy ketones are also called acyloins. [1] They are commonly formed by condensation or reductive coupling of two carbonyl (C=O) compounds or oxidation of ketones. The simplest such compound is hydroxyacetone. If the alcohol is primary, alpha-hydroxy ketones give a positive Fehling's test. Beta-hydroxy ketones are a type of aldol.
Ketones give positive results in Brady's test, the reaction with 2,4-dinitrophenylhydrazine to give the corresponding hydrazone. Ketones may be distinguished from aldehydes by giving a negative result with Tollens' reagent or with Fehling's solution. Methyl ketones give positive results for the iodoform test. [7] Ketones also give positive ...
α-hydroxy ketones give positive Tollens' and Fehling's test. Some acyloins rearrange with positions swapped under the influence of base in the Lobry–de Bruyn–van Ekenstein transformation A similar reaction is the so-called Voigt amination [ 6 ] where an acyloin reacts with a primary amine and phosphorus pentoxide to an α-keto amine: [ 7 ]
Therefore, ketones like fructose are considered reducing sugars but it is the isomer containing an aldehyde group which is reducing since ketones cannot be oxidized without decomposition of the sugar. This type of isomerization is catalyzed by the base present in solutions which test for the presence of reducing sugars. [3]
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