Fructose Created 2026-10-18 Updated 2026-11-05
Fructose is a six-carbon ketose monosaccharide with the same molecular formula as glucose, but different connectivity in the open-chain form. In aqueous chemical solution, fructose occurs mainly in cyclic forms.
Fructose supplies one of the two sugar units in sucrose and is the repeating building block of many fructans. These examples distinguish a free monosaccharide from its residues inside larger carbohydrates.[ref]
25.1 Classification of Carbohydrates. Classification of monosaccharides
John E. McMurry Created 2026-10-24 Updated 2026-11-05
John E. McMurry is the author of an organic chemistry textbook that connects molecular structure with reaction mechanisms. Its treatment of carbohydrates, for example, distinguishes open-chain aldoses and ketoses from the cyclic structures prevalent in solution.
Ketose Created 2026-10-18 Updated 2026-11-05
A ketose is a monosaccharide whose open-chain form contains a ketone group. Fructose is a familiar example, with a carbonyl group at carbon 2 in its open-chain structure.
A ketose can form cyclic structures by reaction of its carbonyl group with one of its own hydroxyl groups. The distinction from an aldose concerns carbonyl connectivity, rather than simply the number of carbon atoms.[ref]
Monosaccharide Created 2026-10-14 Updated 2026-10-18
A monosaccharide is a single-unit carbohydrate that cannot be split into smaller sugars by hydrolysis. Ribose, deoxyribose, and glucose are examples. The unit is a whole molecule containing many chemical atoms; a disaccharide instead contains two linked monosaccharide units.[ref]
25.1 Classification of Carbohydrates. McMurry, Organic Chemistry, §25.1: simple and complex carbohydrates
Classification combines carbon count with open-chain connectivity. An aldose has an aldehyde group; a ketose has a ketone group. Thus glucose is an aldohexose, while fructose is a six-carbon ketose. These names describe the open-chain reference forms even when cyclic forms predominate in water.[ref]
25.1 Classification of Carbohydrates. McMurry, Organic Chemistry, §25.1: aldoses, ketoses and carbon-count classification
Open-chain D-glucose and D-fructose: the same molecular formula, different carbonyl group connectivity
. Original numbered Fischer projections. At tetrahedral stereocenters, horizontal chemical bonds point toward the viewer and vertical chemical bonds away. The carbonyl group carbon is not a tetrahedral stereocenter. The C5 hydroxy group on the right specifies D here; D does not specify the sign of optical rotation. These reference structures do not show relative abundances in water. Details.Check the distinction by counting the groups in the drawings. Open-chain glucose contains one , four and one group. Open-chain fructose contains two , three and one group. The respective hydrogen totals are and ; each structure also has six carbon and six oxygen chemical atoms. Their shared molecular formula therefore cannot identify the carbonyl group position or the stereochemistry.
The beauty is that a familiar sugar name can embrace an interconverting family of forms. Monosaccharide ring-chain interconversion connects those drawings to mutarotation, a change visible with polarimetry. Spatial arrangement also matters to biology: an enzyme's active site encounters a particular arrangement of hydroxy groups, rather than merely an inventory of chemical atoms. The existing enzyme and chirality articles explain that recognition principle.
