stereochemistry Stereochemistry, a subdiscipline of chemistry, studies the spatial arrangement of atoms that form the structure of molecules and their manipulation. The study of stereochemistry focuses on the relationships between stereoisomers, which are defined ...

, an asymmetric carbon is a

carbon Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 ...

atom that is bonded to four different types of atoms or groups of atoms. The four atoms and/or groups attached to the carbon atom can be arranged in space in two different ways that are mirror images of each other, and which lead to so-called ''left-handed'' and ''right-handed'' versions (

stereoisomer In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in ...

s) of the same molecule. Molecules that cannot be superimposed on their own mirror image are said to be

chiral Chirality () is a property of asymmetry important in several branches of science. The word ''chirality'' is derived from the Greek language, Greek (''kheir''), "hand", a familiar chiral object. An object or a system is ''chiral'' if it is dist ...

; as the asymmetric carbon is the center of this chirality, it is also known as a chiral carbon. As an example,

malic acid Malic acid is an organic compound with the molecular formula . It is a dicarboxylic acid that is made by all living organisms, contributes to the sour taste of fruits, and is used as a food additive. Malic acid has two stereoisomeric forms ( ...

() has 4 carbon atoms but just one of them is asymmetric. The asymmetric carbon atom, bolded in the formula, is the one attached to two carbon atoms, an oxygen atom, and a hydrogen atom. One may initially be inclined to think this atom is not asymmetric because it is attached to two carbon atoms, but because those two carbon atoms are not attached to exactly the same things, there are two different ''groups'' of atoms that the carbon atom in question is attached to, therefore making it an asymmetric carbon atom: Knowing the number of asymmetric carbon atoms, one can calculate the maximum possible number of

s for any given molecule as follows: : If is the number of asymmetric carbon atoms then the maximum number of isomers = ( Le Bel-van't Hoff rule) This is a

corollary In mathematics and logic, a corollary ( , ) is a theorem of less importance which can be readily deduced from a previous, more notable statement. A corollary could, for instance, be a proposition which is incidentally proved while proving another ...

of Le Bel and van't Hoff's simultaneously announced conclusions, in 1874, that the most probable orientation of the bonds of a carbon atom linked to four groups or atoms is toward the apexes of a

tetrahedron In geometry, a tetrahedron (: tetrahedra or tetrahedrons), also known as a triangular pyramid, is a polyhedron composed of four triangular Face (geometry), faces, six straight Edge (geometry), edges, and four vertex (geometry), vertices. The tet ...

, and that this accounted for all then-known phenomena of molecular asymmetry (which involved a carbon atom bearing four different atoms or groups). A

tetrose In organic chemistry, a tetrose is a monosaccharide with 4 carbon atoms. They have either an aldehyde () functional group in position 1 (aldotetroses) or a ketone () group in position 2 (ketotetroses). File:DErythrose Fischer.svg , D-Erythrose Fi ...

with 2 asymmetric carbon atoms has 2² = 4 stereoisomers: An

aldopentose In chemistry, a pentose is a monosaccharide (simple sugar) with five carbon atoms. The chemical formula of many pentoses is , and their molecular weight is 150.13 g/mol.aldohexose In chemistry, a hexose is a monosaccharide (simple sugar) with six carbon atoms. The chemical formula for all hexoses is , and their molecular weight is 180.156 g/mol. Hexoses exist in two forms, open-chain or cyclic, that easily convert into e ...

with 4 asymmetric carbon atoms has 2⁴ = 16 stereoisomers:

References

{{DEFAULTSORT:Asymmetric Carbon Stereochemistry Jacobus Henricus van 't Hoff de:Asymmetrisches Kohlenstoffatom