Aliphatic compound

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File:Butan Lewis.svg
Acyclic aliphatic/non-aromatic compound (butane)
File:Cyclobutane2.svg
Cyclic aliphatic/non-aromatic compound (cyclobutane)

In organic chemistry, hydrocarbons (compounds composed solely of carbon and hydrogen) are divided into two classes: aromatic compounds and aliphatic compounds (/ˌælɪˈfætɪk/; G. aleiphar, fat, oil). Aliphatic compounds can be saturated (in which all the C-C bonds are single requiring the structure to be completed, or 'saturated', by hydrogen) like hexane, or unsaturated, like hexene and hexyne. Open-chain compounds, whether straight or branched, and which contain no rings of any type, are always aliphatic. Cyclic compounds can be aliphatic if they are not aromatic.[1]

Structure

Aliphatic compounds can be saturated, joined by single bonds (alkanes), or unsaturated, with double bonds (alkenes) or triple bonds (alkynes). If other elements (heteroatoms) are bound to the carbon chain, the most common being oxygen, nitrogen, sulfur, and chlorine, it is no longer a hydrocarbon, and therefore no longer an aliphatic compound. However, such compounds may still be referred to as aliphatic if the hydrocarbon portion of the molecule is aliphatic, e.g. aliphatic amines, to differentiate them from aromatic amines. The least complex aliphatic compound is methane (CH4).

Properties

Most aliphatic compounds are flammable, allowing the use of hydrocarbons as fuel, such as methane in natural gas for stoves or heating; butane in torches and lighters; various aliphatic (as well as aromatic) hydrocarbons in liquid transportation fuels like petrol/gasoline, diesel, and jet fuel; and other uses such as ethyne (acetylene) in welding.

Examples of aliphatic compounds

The most important aliphatic compounds are:

  • n-, iso- and cyclo-alkanes (saturated hydrocarbons)
  • n-, iso- and cyclo-alkenes and -alkynes (unsaturated hydrocarbons).

Important examples of low-molecular aliphatic compounds can be found in the list below (sorted by the number of carbon-atoms):

Formula Name Structural formula Chemical classification
CH4 Methane File:Methane-2D-stereo.svg Alkane
C2H2 Acetylene File:Ethyne-2D-flat.png Alkyne
C2H4 Ethylene File:Ethene structural.svg Alkene
C2H6 Ethane File:Ethan Lewis.svg Alkane
C3H4 Propyne File:Propyne-2D-flat.png Alkyne
C3H6 Propene File:Propen21.PNG Alkene
C3H8 Propane File:Propane-2D-flat.png Alkane
C4H6 1,2-Butadiene File:Buta-1,2-dien.svg Diene
C4H6 1-Butyne File:Ethylacetylene.svg Alkyne
C4H8 1-Butene File:1-Butene.svg Alkene
C4H10 Butane File:Butane-2D-flat.png Alkane
C6H10 Cyclohexene File:Cyclohexen - Cyclohexene.svg Cycloalkene
C5H12 n-pentane File:Pentan Skelett.svg Alkane
C7H14 Cycloheptane File:Cycloheptane.svg Cycloalkane
C7H14 Methylcyclohexane File:Methylcyclohexane.png Cyclohexane
C8H8 Cubane File:Cuban.svg Prismane, Platonic hydrocarbon
C9H20 Nonane File:Nonan Skelett.svg Alkane
C10H12 Dicyclopentadiene File:Di-Cyclopentadiene ENDO & EXO V.2.svg Diene, Cycloalkene
C10H16 Phellandrene File:Phellandrene alpha.svgFile:Phellandrene beta.svg Terpene, Diene, Cycloalkene
C10H16 α-Terpinene File:Alpha-Terpinene Structure V.1.svg Terpene, Diene, Cycloalkene
C10H16 Limonene File:(R)-Limonen.svgFile:(S)-Limonen.svg Terpene, Diene, Cycloalkene
C11H24 Undecane File:Undecan Skelett.svg Alkane
C30H50 Squalene File:Squalene.svg Terpene, Polyene
C2nH4n Polyethylene File:Polyethylene repeat unit.svg Alkane

References

  1. IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (1995) "aliphatic compounds". doi:10.1351/goldbook.A00217