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mithunb (0)

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Dasvidaniya (2483)

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A bicyclic system (which comprises the main ring and main bridge only) is named by:
• the prefix bicyclo- (indicating the number of rings = 2);
• numbers indicating the bridge lengths (i.e. number of skeletal atoms excluding the bridgehead atoms)
separated by full stops and placed in square brackets. The three numbers are cited in decreasing order of
size (e.g. [3.2.1]);
• the name of the hydrocarbon indicating the total number of skeletal atoms.


Numbering of Bicyclic Systems
The atoms of a bicyclic system are numbered from a bridgehead atom via the longest path to the second
bridgehead atom; numbering of atoms continues round the main ring; and then the main bridge atoms are
numbered starting from the lower numbered bridgehead atom  (Fig.)

 

                                                                           bicyclo [4 3 2 ] undacane


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Dasvidaniya (2483)

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tricyclo[3.2.1.02,4]octane
not tricyclo[4.1.0.12,5]octane  (one-atom main bridge larger than no-atom bridge)

 

 

                                                                                              
bicyclo[3.2.1]octane

 

 


bicyclo[3.2.1]octane
not bicyclo[3.1.2]octane (7-membered main ring larger than 6)

 

 


tricyclo[4.4.1.13,9]dodecane
not tricyclo[4.3.2.13,8]dodecane (10-membered main ring larger than 9)


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aditya vardhan (28)

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 You can find some nice explanation and examples for IUPAC nomenclature at: http://www.adichemistry.com/organic/organic-chemistry.html


Visit AdiChemistry: An Online Resource of Chemistry Study Material. This site is an internationally acclaimed site for chemistry study material
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Juhi Sharma (1527)

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A bicyclic molecule is a molecule that features two fused rings. Bicyclic molecules occur widely in organic and inorganic compounds.

Fusion of the rings can occur in three ways:

·         Across a bond between two atoms - for example, decalin (also known as bicyclo[4.4.0]decane), has a C-C bond shared between two cyclohexane rings;

·         Across a sequence of atoms (bridgehead) - for example, norbornane (also known as bicyclo[2.2.1]heptane), can be viewed as a pair of cyclopentane rings that share three of the five carbon atoms; or

·         At a single atom (spirocyclic, forming a spiro compound)

Bicyclic molecules have a strict nomenclature. On its simplest level the parent hydrocarbon is the equivalent open carbon alkane. For bridged compounds, the prefix bicyclo is added, followed by, between brackets, separated by periods, and in descending order, the number of carbon atoms between each of the bridgeheads. For example in bicyclo[2.2.1]heptane the carbon frame contains a total of 7 atoms hence the parent name heptane. This molecule has three bridges having 2, 2 and 1 carbon atoms hence the prefix bicyclo[2.2.1]. For spiro compounds, terms like spiro[2.4] are used, indicating that there are 3- and 5-membered rings (because the spiro atom itself is not counted) meeting at the spiro atom.

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