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Norbornene or norbornylene or norcamphene is a bridged cyclic hydrocarbon
Hydrocarbon

In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. With relation to chemical terminology, aromatic hydrocarbons or arenes, alkanes, alkenes and alkyne-based compounds composed entirely of carbon or hydrogen are referred to as "pure" hydrocarbons, whereas other hydrocarbons with bonded com...
. It is a white solid with a pungent sour odor. The molecule
Molecule

In chemistry, a molecule is defined as a sufficiently stable, electric charge neutral group of at least two atoms in a definite arrangement held together by very strong chemical bonds....
 consists of a cyclohexene
Cyclohexene

Cyclohexene is a colorless clear liquid cycloalkene with an intense aversive characteristic sharp smell reminiscent of an oil refinery.It is not very stable upon long term storage with exposure to light and air and should be distilled before use to eliminate organic peroxide....
 ring bridged with a methylene
Methylene

Methylene is the chemical species, R2C:, named after methane, in which two of the carbon atom's valence electrons form no bonds. The word is applicable to:...
 group in the para position
Arene substitution patterns

Arene substitution patterns are part of organic chemistry IUPAC nomenclature and pinpoint the position of substituents other than hydrogen in relation to each other on an aromatic hydrocarbon....
. The molecule carries a double bond which induces significant ring strain
Ring strain

Ring strain is an organic chemistry term that describes the destabilization of a cyclic molecule?such as a cycloalkane?due to the non-favorable high energy Molecular geometry of its atoms....
 and significant reactivity.

Norbornene, like many of its derivatives, is made by a Diels-Alder reaction
Diels-Alder reaction

The Diels-Alder reaction is an organic chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene system....
 of cyclopentadiene
Cyclopentadiene

Cyclopentadiene is a chemical compound with the Chemical formula C5H6. This colorless liquid organic chemistry chemical compound has a strong and unpleasant odor....
 and ethylene
Ethylene

Ethylene is the chemical compound with the formula C2H4. It is the simplest alkene. Because it contains a carbon-carbon double bond, ethylene is called an unsaturated hydrocarbon or an olefin....
. Related bicyclics are norbornadiene
Norbornadiene

Norbornadiene is a bicyclic hydrocarbon. The molecule can be envisioned as a 1,4-cyclohexadiene bridged in the aromatic para position positions by a methylene group....
 which has the same carbon skeleton but with two double bonds and norbornane
Norbornane

Norbornane is an organic compound and a saturated compound hydrocarbon with chemical formula C7H12. It is a crystalline compound with melting point 88 ?C....
 which is completely saturated without double bonds.

Norbornene undergoes an acid-catalyzed hydration reaction
Hydration reaction

In organic chemistry, a hydration reaction is a chemical reaction in which a hydroxyl group and a hydrogen cation are added to the two carbon atoms covalent bonded together in the carbon-carbon double bond which makes up an alkene functional group....
 with water to form norborneol
Norborneol

Norborneol may refer to:*endo-Norborneol*exo-Norborneol...
.






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Norbornene or norbornylene or norcamphene is a bridged cyclic hydrocarbon
Hydrocarbon

In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. With relation to chemical terminology, aromatic hydrocarbons or arenes, alkanes, alkenes and alkyne-based compounds composed entirely of carbon or hydrogen are referred to as "pure" hydrocarbons, whereas other hydrocarbons with bonded com...
. It is a white solid with a pungent sour odor. The molecule
Molecule

In chemistry, a molecule is defined as a sufficiently stable, electric charge neutral group of at least two atoms in a definite arrangement held together by very strong chemical bonds....
 consists of a cyclohexene
Cyclohexene

Cyclohexene is a colorless clear liquid cycloalkene with an intense aversive characteristic sharp smell reminiscent of an oil refinery.It is not very stable upon long term storage with exposure to light and air and should be distilled before use to eliminate organic peroxide....
 ring bridged with a methylene
Methylene

Methylene is the chemical species, R2C:, named after methane, in which two of the carbon atom's valence electrons form no bonds. The word is applicable to:...
 group in the para position
Arene substitution patterns

Arene substitution patterns are part of organic chemistry IUPAC nomenclature and pinpoint the position of substituents other than hydrogen in relation to each other on an aromatic hydrocarbon....
. The molecule carries a double bond which induces significant ring strain
Ring strain

Ring strain is an organic chemistry term that describes the destabilization of a cyclic molecule?such as a cycloalkane?due to the non-favorable high energy Molecular geometry of its atoms....
 and significant reactivity.

Norbornene, like many of its derivatives, is made by a Diels-Alder reaction
Diels-Alder reaction

The Diels-Alder reaction is an organic chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene system....
 of cyclopentadiene
Cyclopentadiene

Cyclopentadiene is a chemical compound with the Chemical formula C5H6. This colorless liquid organic chemistry chemical compound has a strong and unpleasant odor....
 and ethylene
Ethylene

Ethylene is the chemical compound with the formula C2H4. It is the simplest alkene. Because it contains a carbon-carbon double bond, ethylene is called an unsaturated hydrocarbon or an olefin....
. Related bicyclics are norbornadiene
Norbornadiene

Norbornadiene is a bicyclic hydrocarbon. The molecule can be envisioned as a 1,4-cyclohexadiene bridged in the aromatic para position positions by a methylene group....
 which has the same carbon skeleton but with two double bonds and norbornane
Norbornane

Norbornane is an organic compound and a saturated compound hydrocarbon with chemical formula C7H12. It is a crystalline compound with melting point 88 ?C....
 which is completely saturated without double bonds.

Norbornene undergoes an acid-catalyzed hydration reaction
Hydration reaction

In organic chemistry, a hydration reaction is a chemical reaction in which a hydroxyl group and a hydrogen cation are added to the two carbon atoms covalent bonded together in the carbon-carbon double bond which makes up an alkene functional group....
 with water to form norborneol
Norborneol

Norborneol may refer to:*endo-Norborneol*exo-Norborneol...
. This reaction is of great interest to chemists studying 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....
s.

Polynorbornenes


Norbornenes are important monomer
Monomer

A monomer is a small molecule that may become Chemistry chemical bonding to other monomers to form a polymer....
s in ring-opening metathesis polymerizations (ROMP) with for instance the Grubbs' catalyst
Grubbs' catalyst

Grubbs' Catalyst is a transition metal carbene complex named after the chemist by whom it was first synthesized, Robert H. Grubbs. There are two generations of the catalyst, as shown on the right....
. Polynorbornenes are polymer
Polymer

A polymer is a large molecule composed of repeating structural units typically connected by covalent chemical bonds. While polymer in popular usage suggests plastic, the term actually refers to a large class of natural and synthetic materials with a variety of properties....
s with high glass transition temperature
Glass transition temperature

The Glass transition temperature, Tg, is the temperature at which an amorphous solid, such as glass or a polymer, becomes wikt:brittle on cooling, or soft on heating....
s and high optical clarity.

In addition to ROMP polymerization, norbornene monomers also undergo vinyl-addition polymerization.

Ethylidene norbornene is a related monomer derived from cyclopentadiene
Cyclopentadiene

Cyclopentadiene is a chemical compound with the Chemical formula C5H6. This colorless liquid organic chemistry chemical compound has a strong and unpleasant odor....
 and butadiene.

Practical Uses

Norbornene does not have as many practical uses as ethylene
Ethylene

Ethylene is the chemical compound with the formula C2H4. It is the simplest alkene. Because it contains a carbon-carbon double bond, ethylene is called an unsaturated hydrocarbon or an olefin....
 or other commodity chemicals. It is utilized to make pharmaceutical intermediates, pesticide compounds, specialty fragrances and in general organic synthesis. When combined with ethylene, norbornene will react and turn into a cyclic olefin copolymer
Cyclic Olefin Copolymer

Cyclic Olefin Copolymer is an amorphous polymer made by several polymer manufacturers. COC is a relatively new class of polymers when compared to polypropylene and polyethylene....
.