any of a class of organic chemical compounds composed only of the elements carbon (C) and hydrogen (H). The carbon atoms join together to form the framework of the compound; the hydrogen atoms attach to them in many different configurations. Hydrocarbons are the principal constituents of petroleum and natural gas. They serve as fuels and lubricants as well as raw materials for the production of plastics, fibres, rubbers, solvents, explosives, and industrial chemicals.
Many hydrocarbons occur in nature. In addition to making up fossil fuels, they are present in trees and plants, as, for example, in the form of pigments called carotenes that occur in carrots and green leaves. More than 98 percent of natural crude rubber is a hydrocarbon polymer, a chainlike molecule consisting of many units linked together. The structures and chemistry of individual hydrocarbons depend in large part on the types of chemical bonds that link together the atoms of their constituent molecules.
Nineteenth-century chemists classified hydrocarbons as either aliphatic or aromatic on the basis of their sources and properties. Aliphatic (from Greek aleiphar, “fat”) described hydrocarbons derived by chemical degradation of fats or oils. Aromatic hydrocarbons constituted a group of related substances obtained by chemical degradation of certain pleasant-smelling plant extracts. The terms aliphatic and aromatic are retained in modern terminology, but the compounds they describe are distinguished on the basis of structure rather than origin.
Aliphatic hydrocarbons are divided into three main groups according to the types of bonds they contain: alkanes, alkenes, and alkynes. Alkanes have only single bonds, alkenes contain a carbon-carbon double bond, and alkynes contain a carbon-carbon triple bond. Aromatic hydrocarbons are those that are significantly more stable than their Lewis structures would suggest; i.e., they possess “special stability.” They are classified as either arenes, which contain a benzene ring as a structural unit, or nonbenzenoid aromatic hydrocarbons, which possess special stability but lack a benzene ring as a structural unit.
This classification of hydrocarbons serves as an aid in associating structural features with properties but does not require that a particular substance be assigned to a single class. Indeed, it is common for a molecule to incorporate structural units characteristic of two or more hydrocarbon families. A molecule that contains both a carbon-carbon triple bond and a benzene ring, for example, would exhibit some properties that are characteristic of alkynes and others that are characteristic of arenes.
Alkanes are described as saturated hydrocarbons, while alkenes, alkynes, and aromatic hydrocarbons are said to be unsaturated.
Alkanes, hydrocarbons in which all the bonds are single, have molecular formulas that satisfy the general expression CnH2n + 2 (where n is an integer). Carbon is sp3 hybridized (three electron pairs are involved in bonding, forming a tetrahedral complex), and each C—C and C—H bond is a sigma (σ) bond (see chemical bonding). In order of increasing number of carbon atoms, methane (CH4), ethane (C2H6), and propane (C3H8) are the first three members of the series.
Methane, ethane, and propane are the only alkanes uniquely defined by their molecular formula. For C4H10 two different alkanes satisfy the rules of chemical bonding (namely, that carbon has four bonds and hydrogen has one in neutral molecules). One compound, called n-butane, where the prefix n- represents normal, has its four carbon atoms bonded in a continuous chain. The other, called isobutane, has a branched chain.
Different compounds that have the same molecular formula are called isomers. Isomers that differ in the order in which the atoms are connected are said to have different constitutions and are referred to as constitutional isomers. (An older name is structural isomers.) The compounds n-butane and isobutane are constitutional isomers and are the only ones possible for the formula C4H10. Because isomers are different compounds, they can have different physical and chemical properties. For example, n-butane has a higher boiling point (−0.5 °C [31.1 °F]) than isobutane (−11.7 °C [10.9 °F]).
There is no simple arithmetic relationship between the number of carbon atoms in a formula and the number of isomers. Graph theory has been used to calculate the number of constitutionally isomeric alkanes possible for values of n in CnH2n + 2 from 1 through 400. The number of constitutional isomers increases sharply as the number of carbon atoms increases. There is probably no upper limit to the number of carbon atoms possible in hydrocarbons. The alkane CH3(CH2)388CH3, in which 390 carbon atoms are bonded in a continuous chain, has been synthesized as an example of a so-called superlong alkane. Several thousand carbon atoms are joined together in molecules of hydrocarbon polymers such as polyethylene, polypropylene, and polystyrene.
| Number of possible alkane isomers | |
| molecular formula | number of constitutional isomers |
| C3H8 | 1 |
| C4H10 | 2 |
| C5H12 | 3 |
| C6H14 | 5 |
| C7H16 | 9 |
| C8H18 | 18 |
| C9H20 | 35 |
| C10H22 | 75 |
| C15H32 | 4,347 |
| C20H42 | 366,319 |
| C30H62 | 4,111,846,763 |
Structures-assumed-by-hydrogen-and-carbon-molecules-in-four-commonStructures assumed by hydrogen (H) and carbon (C) molecules in four common hydrocarbon compounds.
The-tetrahedral-geometry-of-methane-stick-and-ball-model-andThe tetrahedral geometry of methane: (A) stick-and-ball model and (B) showing bond angles and …[Credits : Encyclopædia Britannica, Inc.]
Eclipsed-conformation-is-the-least-stable-of-all-ethane-conformationsEclipsed conformation is the least stable of all ethane conformations because the repulsive forces …[Credits : Encyclopædia Britannica, Inc.]
Staggered-conformation-is-the-most-stable-of-all-ethane-conformationsStaggered conformation is the most stable of all ethane conformations because the repulsive forces …[Credits : Encyclopædia Britannica, Inc.]
Benzene-is-the-smallest-of-the-organic-aromatic-hydrocarbonsBenzene is the smallest of the organic aromatic hydrocarbons. It contains sigma bonds (represented …[Credits : Encyclopædia Britannica, Inc.]
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