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Alicyclic compound

From Wikipedia, the free encyclopedia
Organic molecule with one or more non-aromatic all-carbon rings
"Carbon ring" redirects here. For aromatic carbon rings, seeAromaticity.

Inorganic chemistry, analicyclic compound contains one or more all-carbonrings which may be eithersaturated or unsaturated, but do not havearomatic character.[1] Alicyclic compounds may have one or morealiphaticside chains attached.

Cycloalkanes

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Further information:Cycloalkane
Cyclopropane is the smallest alicyclic compound.

The simplest alicyclic compounds are the monocycliccycloalkanes:cyclopropane,cyclobutane,cyclopentane,cyclohexane,cycloheptane,cyclooctane, and so on.Bicyclic alkanes includedecalin,housane, andnorbornane.Polycyclic alkanes includecubane,basketane, andtetrahedrane.

Spiro compounds have two or more rings that are connected through only one carbon atom.

The mode of ring-closing in the formation of many alicyclic compounds can be predicted byBaldwin's rules.

Otto Wallach, a German chemist, received the 1910Nobel Prize in Chemistry for his work on alicyclic compounds.[2][3]

Cycloalkenes

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Further information:Cycloalkene
Cyclohexene is an alicyclic compound with a double bond.

Monocycliccycloalkenes arecyclopropene,cyclobutene,cyclopentene,cyclohexene,cycloheptene,cyclooctene, and so on. Bicyclic alkenes includenorbornene andnorbornadiene.

Two more examples are shown below,methylenecyclohexane on the left and1-methylcyclohexene on the right:

Left: exocyclic double bond
Right: regular double bond

Anexocyclic group is always shown outside the ring structure, take for instance the exocyclic double bond of the former molecule.Isotoluenes are a prominent class of compounds with exocyclic double bonds.

The placement of double bonds in many alicyclic compounds can be predicted withBredt's rule.

References

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  1. ^IUPAC,Compendium of Chemical Terminology, 5th ed. (the "Gold Book") (2025). Online version: (1995) "Alicyclic compounds".doi:10.1351/goldbook.A00216
  2. ^Leopold Ruzicka (1932). "Third Pedler lecture. The life and work of Otto Wallach".J. Chem. Soc.: 1582.doi:10.1039/JR9320001582.
  3. ^Christmann, M (2010). "Otto Wallach: Founder of Terpene Chemistry and Nobel Laureate 1910".Angewandte Chemie International Edition.49 (50):9580–9586.doi:10.1002/anie.201003155.PMID 21110354.
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