Norbornane (also known as bicyclo
.2.1eptane) is an
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. Th ...
and a
saturated hydrocarbon
In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic, and their odors are usually weak or ...
with
chemical formula
In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, ...
C
7H
12. It is a
crystalline
A crystal or crystalline solid is a solid material whose constituents (such as atoms, molecules, or ions) are arranged in a highly ordered microscopic structure, forming a crystal lattice that extends in all directions. In addition, macros ...
compound with a
melting point
The melting point (or, rarely, liquefaction point) of a substance 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 depen ...
of 88
°C
The degree Celsius is the unit of temperature on the Celsius scale (originally known as the centigrade scale outside Sweden), one of two temperature scales used in the International System of Units (SI), the other being the Kelvin scale. The d ...
. The carbon skeleton is derived from
cyclohexane
Cyclohexane is a cycloalkane with the molecular formula . Cyclohexane is non-polar. Cyclohexane is a colorless, flammable liquid with a distinctive detergent-like odor, reminiscent of cleaning products (in which it is sometimes used). Cyclohe ...
ring with a
methylene bridge in the 1,4- position, and is a bridged
bicyclic compound. The compound is a prototype of a class of strained bicyclic hydrocarbons.
The compound was originally synthesized by reduction of
norcamphor.
The name norbornane is derived from
bornane, which is 1,7,7-trimethylnorbornane, being a derivative of
camphor
Camphor () is a waxy, colorless solid with a strong aroma. It is classified as a terpenoid and a cyclic ketone. It is found in the wood of the camphor laurel (''Cinnamomum camphora''), a large evergreen tree found in East Asia; and in the k ...
(bornanone). The prefix
''nor'' refers to the stripping of the methyl groups from the parent molecule bornane.
See also
*
2-Norbornyl cation
In organic chemistry, the term 2-norbornyl cation (or 2-bicyclo .2.1eptyl cation) describes one of the three carbocations formed from derivatives of norbornane. Though 1-norbornyl and 7-norbornyl cations have been studied, the most extensive studie ...
*
Norbornene
Norbornene or norbornylene or norcamphene is a highly strained bridged cyclic hydrocarbon. It is a white solid with a pungent sour odor. The molecule consists of a cyclohexene ring with a methylene bridge between carbons 1 and 4. The molecule car ...
*
Norbornadiene
Norbornadiene is an organic compound and a bicyclic hydrocarbon. Norbornadiene is of interest as a metal-binding ligand, whose complexes are useful for homogeneous catalysis. It has been intensively studied owing to its high reactivity and distin ...
*
Bornane
*
endo-Norborneol
*
exo-Norborneol
*
Norcamphor, the ketone derivative of norbornane
References
{{Reflist
External links
Norbornane in 3DDatasheet at ''Sigma-Aldrich''
Bicycloalkanes
Cyclopentanes