Norbornane
Encyclopedia
Norbornane is an organic compound
and a saturated hydrocarbon
with chemical formula
C7H12. It is a crystalline compound with melting point
88 °C. The carbon skeleton is a cyclohexane
ring bridged by a methylene
group in the 1,4- position, and is a bridged bicyclic compound. The compound can be synthesized by hydrogenation
of the related compounds norbornene
and norbornadiene
. The norbornyl cation (C7H11+) is of great scientific interest in relation to non-classical ion
s.
The compound got its name from bornane
which has three methyl groups and is the carbon skeleton for camphor
(bornanone). In bornane, there is one methyl group attached to a carbon at the base of the bridge and two methyl groups attached to the carbon at the apex of the bridge. The prefix nor refers to the stripping of the methyl groups from the original bornane.
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
and a saturated hydrocarbon
Hydrocarbon
In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons from which one hydrogen atom has been removed are functional groups, called hydrocarbyls....
with chemical formula
Chemical formula
A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....
C7H12. It is a crystalline compound with melting point
Melting point
The melting point of a solid is the temperature at which it changes state from solid to liquid. At the melting point the solid and liquid phase exist in equilibrium. The melting point of a substance depends on pressure and is usually specified at standard atmospheric pressure...
88 °C. The carbon skeleton is a cyclohexane
Cyclohexane
Cyclohexane is a cycloalkane with the molecular formula C6H12. Cyclohexane is used as a nonpolar solvent for the chemical industry, and also as a raw material for the industrial production of adipic acid and caprolactam, both of which being intermediates used in the production of nylon...
ring bridged by a methylene
Methylene
Methylene is a chemical species in which a carbon atom is bonded to two hydrogen atoms. Three different possibilities present themselves:* the -CH2- substituent group: e.g., dichloromethane ....
group in the 1,4- position, and is a bridged bicyclic compound. The compound can be synthesized by hydrogenation
Hydrogenation
Hydrogenation, to treat with hydrogen, also a form of chemical reduction, is a chemical reaction between molecular hydrogen and another compound or element, usually in the presence of a catalyst. The process is commonly employed to reduce or saturate organic compounds. Hydrogenation typically...
of the related compounds norbornene
Norbornene
Norbornene or norbornylene or norcamphene is a bridged cyclic hydrocarbon. It is a white solid with a pungent sour odor. The molecule consists of a cyclohexene ring bridged with a methylene group in the para position...
and norbornadiene
Norbornadiene
Norbornadiene is an organic compound. This bicyclic hydrocarbon is the most stable diolefin derived from the norbornane and norbornene. Norbornadiene is primarily of interest as a ligand in homogeneous catalysis, but it has been heavily studied due to its high reactivity and distinctive...
. The norbornyl cation (C7H11+) is of great scientific interest in relation to non-classical ion
Non-classical ion
Non-classical ions in organic chemistry are a special type of carbonium ions displaying delocalization of sigma bonds in 3-center-2-electron bonds of bridged systems. The term non-classical ion was first used by John D...
s.
The compound got its name from bornane
Bornane
Bornane is a compound closely related to norbornane....
which has three methyl groups and is the carbon skeleton for camphor
Camphor
Camphor is a waxy, white or transparent solid with a strong, aromatic odor. It is a terpenoid with the chemical formula C10H16O. It is found in wood of the camphor laurel , a large evergreen tree found in Asia and also of Dryobalanops aromatica, a giant of the Bornean forests...
(bornanone). In bornane, there is one methyl group attached to a carbon at the base of the bridge and two methyl groups attached to the carbon at the apex of the bridge. The prefix nor refers to the stripping of the methyl groups from the original bornane.