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Basic IUPAC Organic Nomenclature

Spirocyclic alkanes

basic spiro numbering




STUDY TIP
In spiro systems, number the smallest ring first
spiro = smallest

  • Functional group is an alkane, therefore suffix = -ane
  • The ring structure requires the prefix spiro
  • The ring structure is C5 therefore root = pent
  • Excluding the spirocenter, there are two C atoms in each ring = [2.2]
spiro[2.2]pentane
spiro
  • Functional group is an alkane, therefore suffix = -ane
  • The ring structure requires the prefix spiro
  • The ring structure is C8 therefore root = oct
  • Excluding the spirocenter, one ring has two C atoms and the other has five C atoms = [2.5]
spiro[2.5]octane
spiro



  • Functional group is an alkane, therefore suffix = -ane
  • The ring structure requires the prefix spiro
  • The ring structure is C9 therefore root = non
  • Excluding the spirocenter, one ring has three C atoms and the other has five C atoms = [3.5]
  • There is a C1 substituent = methyl group
  • The lowest locant (first point of difference) = 5
5-methylspiro[3.5]nonane
spiro
Show spirocenter


  • Functional group is an alkane, therefore suffix = -ane
  • The ring structure requires the prefix spiro
  • The ring structure is C9 therefore root = non
  • Excluding the spirocenter, one ring has three C atoms and the other has five C atoms = [3.5]
  • There is a C1 substituent = methyl group
  • The lowest locant (first point of difference) = 1
1-methylspiro[3.5]nonane
spiro
Show spirocenter



 
organic chemistry ©Dr. Ian Hunt, Department of Chemistry University of Calgary