One type of these compounds can be detected via the reduction of copper acetate to copper oxide in Barfoed's test, while two different types of these compounds can be distinguished using a solution of
One type of these compounds can be detected via the reduction of copper acetate to copper oxide in Barfoed's test, while two different types of these compounds can be distinguished using a solution of resorcinol and hydrochloric acid in Seliwanoff's test. These compounds isomerize through an enediol intermediate via the Lobry de Bruyn-van Ekenstein reaction. These compounds can be shortened by one carbon by oxidizing them with bromine water, then adding ferric acetate and hydrogen peroxide. Conversely, these compounds can be elongated by one carbon via the formation of a cyanohydrin intermediate which is reduced by a palladium-catalyzed hydrogenation or a sodium amalgam. These compounds, which can be shortened or lengthened by the Ruff degradation and the Kiliani-Fischer synthesis, have an asymmetric carbon in their hemiacetal group called the anomeric carbon. These compounds are typically visualized using Haworth or Fischer projections. For 10 points, name this type of compound exemplified by mannose and glucose.