Norbornane (norkamfan, bicyclo [2.2.1] heptane is a bicyclic hydrocarbon. It is a structural fragment of borneol and camphor molecules.
| Norbornan | |
|---|---|
 | |
| Are common | |
| Chem. formula | C 7 H 12 |
| Physical properties | |
| Molar mass | 96.17 g / mol |
| Thermal properties | |
| T. melt. | 87.5-87.8 ° C |
| Enthalpy of Education | -52.7 kJ / mol |
| Classification | |
| Reg. CAS number | |
| PubChem | |
| Reg. EINECS number | |
| Smiles | |
| Inchi | |
| Chebi | |
| ChemSpider | |
Properties
Norbornane is a crystalline substance containing two cycles in its molecule. The cyclohexane ring in the molecule is built in the form of a bath, due to the presence of the second cycle, it leads to the appearance of high stresses in the molecule (60.5 kJ / mol). Enters into stereospecific ionic and radical substitution reactions with the formation of exclusively exo derivatives, for example, with sulfuryl chloride and dimethyl sulfate forms 2- exo- chlorornorbornane, with oxalyl chloride and benzoyl peroxide and then with methanol - exo- bicyclo [2.2.1] heptane-2 acid.
Norbornane can also enter into the reactions of rearrangement of the carbon skeleton - camphene rearrangements .
Receiving and applying
Norbornane and its derivatives are synthesized from norbornene and norbornadiene by hydrogenation. Norbornene is used in laboratory practice to study stereochemistry and reaction mechanisms.
Literature
- Chemical Encyclopedia / Editorial Board: Knunyants I.L. et al. - M .: Soviet Encyclopedia, 1992. - T. 3 (Med-Paul). - 639 p. - ISBN 5-82270-039-8 .