organic chemistry Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J.; ...

, ''endo''–''exo'' isomerism is a special type of

stereoisomerism 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 ...

found in

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

s with a

substituent A substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. (In organic chemistry and biochemistry, the terms ''substituent'' and ''functional group'', as well as ''side ...

on a bridged ring system. The prefix ''endo'' is reserved for the

isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers. Iso ...

with the substituent located closest, or "''syn''", to the longest bridge. The prefix ''exo'' is reserved for the isomer with the substituent located farthest, or "''anti''", to the longest bridge. Here "longest" and "shortest" refer to the number of atoms that comprise the bridge. This type of

molecular geometry Molecular geometry is the three-dimensional arrangement of the atoms that constitute a molecule. It includes the general shape of the molecule as well as bond lengths, bond angles, torsional angles and any other geometrical parameters that determ ...

is found in

norbornane Norbornane (also known as bicyclo .2.1eptane) is an organic compound and a saturated hydrocarbon with chemical formula C7H12. It is a crystalline compound with a melting point of 88 °C. The carbon skeleton is derived from cyclohexane ring with a ...

systems such as

dicyclopentadiene Dicyclopentadiene, abbreviated DCPD, is a chemical compound with formula C10H12. At room temperature, it is a white brittle wax, although lower purity samples can be straw coloured liquids. The pure material smells somewhat of soy wax or camphor ...

. The terms ''endo'' and ''exo'' are used in a similar sense in discussions of the stereoselectivity in Diels–Alder reactions.

References

* {{Navbox stereochemistry Stereochemistry