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Alkane

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Alkanes are a fundamental class of organic compounds known as acyclic saturated hydrocarbons.

Methane-2D-stereo
Methane-2D-stereo

This means they consist entirely of carbon and hydrogen atoms. In an alkane, every carbon atom is saturated with hydrogen. This occurs because the carbon atoms are joined only by single bonds. These single bonds allow each carbon to hold the maximum number of hydrogen atoms possible. The International Union of Pure and Applied Chemistry (IUPAC) defines them as unbranched or branched chains. Some scientists also use the term to include cycloalkanes, which are molecules where the atoms form rings.

Saturated C4 hydrocarbons ball-and-stick (C4H10 C4H8)
Saturated C4 hydrocarbons ball-and-stick (C4H10 C4H8)

To understand how an alkane is built, we must look at its molecular structure. Each carbon atom in an alkane is sp3-hybridized. This specific type of orbital hybridization results in four sigma bonds for every carbon. These bonds can connect to other carbon atoms or to hydrogen atoms. The longest continuous chain of these carbon atoms is called the carbon backbone or skeleton.

CH4-structure
CH4-structure

All alkanes belong to a homologous series. This means they follow a repeating pattern of methylene units, or -CH2- groups. Because of this pattern, each member of the series differs from the next by a molecular mass of 14.03 u. This mass comes from one carbon atom and two hydrogen atoms.

Ch4 hybridization
Ch4 hybridization

Alkanes can exist in several different structural forms. The simplest form is a linear chain, often called an n-isomer. However, the carbon backbone can also branch out to create different shapes. These different arrangements of the same atoms are called structural isomers. For example, C4H10 can exist as both butane and isobutane. As the number of carbon atoms increases, the number of possible isomers grows rapidly. A molecule with 10 carbons has 75 possible isomers. By the time you reach 60 carbons, there are over 22 sextillion possible arrangements.

Pentane-2D-Skeletal
Pentane-2D-Skeletal

Beyond linear and branched chains, there are cycloalkanes. These are hydrocarbons where the carbon atoms are joined in one or more rings. While some sources group them with alkanes, they have a different general formula. For instance, a cycloalkane with five carbons has the formula C5H10, whereas a straight-chain pentane is C5H12.

Pentane-2D-Skeletal
Pentane-2D-Skeletal

There are also branched alkanes that can be chiral. This means they have a specific spatial arrangement that makes them non-superimposable on their mirror images. An example is 3-methylhexane, which has a stereogenic center at the third carbon atom.

Scientists have developed specific systems to name these complex molecules. In 1866, August Wilhelm von Hofmann suggested a system using vowel suffixes. He used -ane, -ene, -ine, -one, and -une to distinguish different types of hydrocarbons. Modern IUPAC nomenclature has refined this. We now use Greek prefixes to indicate the number of carbon atoms. For example, "meth-" is for one carbon and "eth-" is for two. To name a branched molecule, you must find the longest continuous carbon chain first. Then, you identify and number the side chains, which are called alkyl groups.

Isopentane-numbered-3D-balls
Isopentane-numbered-3D-balls

Physical properties of alkanes change based on their molecular weight. All alkanes are colorless. Small alkanes with low molecular weights, like methane, are gases at standard temperature and pressure.

AlkaneBoilingMeltingPoint
AlkaneBoilingMeltingPoint

As the carbon chain gets longer, the molecules become liquids. For example, octane is a liquid. Once the carbon backbone exceeds about 17 atoms, the alkanes become solid waxes. These heavier alkanes are used for various industrial and natural purposes.

Oil well
Oil well

Alkanes are highly significant in both nature and industry. Most of our commercial alkanes come from petroleum or natural gas.

ShellMartinez-refi
ShellMartinez-refi

In the biological world, methane is produced by tiny organisms called methanogenic archaea.

Rotbuntes Rind
Rotbuntes Rind

Some long-chain alkanes serve as protective waxes for plants and fungi. Certain animals even use these molecules as pheromones for communication. Even in space, alkanes are present; methane is a major component of the atmosphere on Jupiter.

Jupiter
Jupiter
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🖼️ Images & Media (17)
File:Methane-2D-stereo.svg
Methane-2D-stereo.svg
File:Saturated C4 hydrocarbons ball-and-stick (C4H10 C4H8).png
Saturated C4 hydrocarbons ball-and-stick...
File:Isopentane-numbered-3D-balls.png
Isopentane-numbered-3D-balls.png
File:Pentane-2D-Skeletal.svg
Pentane-2D-Skeletal.svg
File:Isopentane-2D-skeletal.svg
Isopentane-2D-skeletal.svg
File:Neopentane-2D-skeletal.svg
Neopentane-2D-skeletal.svg
File:AlkaneBoilingMeltingPoint.png
AlkaneBoilingMeltingPoint.png
File:Ch4 hybridization.svg
Ch4 hybridization.svg
File:CH4-structure.svg
CH4-structure.svg
File:Newman projection ethane.png
Newman projection ethane.png
File:Ethane-rotamers-3D-balls.png
Ethane-rotamers-3D-balls.png
File:Monobromination of propane.png
Monobromination of propane.png

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