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Editors: K. Lee Lerner and Brenda Wilmoth Lerner
Date: Mar. 20, 2013
Publisher: Gale
Document Type: Topic overview
Length: 1,406 words
Content Level: (Level 4)
Lexile Measure: 1260L

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Hydrocarbons are compounds composed solely of carbon and hydrogen. Despite their simple composition, hydrocarbons include a large number of different compounds with a variety of chemical properties. Hydrocarbons derived from oil deposits are the source of gasoline, heating oil, and other fossil fuels. Found in a variety of geological settings, hydrocarbons provide the carbon skeletons required for the thousands of chemicals produced by the chemical industry.

Since hydrocarbons are nonpolar, they are generally insoluble in water, and they dissolve in nonpolar solvents.

Hydrocarbons are classified on the basis of their structure and bonding. The three major classes are aliphatics, alicyclics, and aromatics. Aliphatics have carbon backbones that form straight or branched chains with no rings. Alicyclics are ring compounds that, while they may have one or more double bonds, do not (like benzene) form conjugated sets of double bonds around the ring. Aromatics are compounds with at least one benzene ring. Aliphatic means fatty, and aromatic refers to odor, but these terms no longer have significance for the compounds they describe.

The aliphatic hydrocarbons are further divided into alkanes, alkenes, and alkynes. Alkanes (sometimes called paraffins) have only single bonds, while alkenes (sometimes called olefins) have a carbon-carbon double bond, and alkynes have a carbon-carbon triple bond. Compounds with two double bonds are known as dienes. Compounds with double or triple bonds are referred to as "unsaturated," while those without these types of bonds are "saturated," meaning all of their carbons are bonded to the maximum number of hydrogen atoms.

All alkanes have the general formula CnH2n+2, where n is the number of carbon atoms in the compound. Alkenes have the formula CnH2n, while alkynes are CnH2n-2. Due to these regularities, the members of each group are known as a homologous series.

The simplest alkane (and indeed, the simplest hydrocarbon) is methane, CH4. The four C-H bonds are directed toward the four corners of a tetrahedron, with carbon at its center and a hydrogen at each vertex. The C-H bonds are slightly polar and equivalent in length and strength. The angle formed by any pair of bonds is 109.5°, the tetrahedral angle.

Despite the bond polarity, there is no net dipole because of the symmetry of the molecule, and methane has very weak intermolecular attractions, consisting only of van der Waals attractions. These attractions are proportional to surface area, which is small for the compact methane molecule. As a result, methane has a very low melting point and boiling point, -297.4°F (-183°C) and -258.7°F (-161.5°C), respectively.

Methane is found in oil deposits and forms the majority of the natural gas fraction. Certain anaerobic bacteria also produce methane, especially in swampy bottoms, where methane bubbles to the surface as marsh gas. Methane is used in large quantities as a fuel for heating and cooking because it burns with oxygen to produce carbon dioxide and water. Methane burns cleanly, with very little soot or smoke. The majority of the world's methane deposits lie in methane hydrate, also known as methane clathrate. Methane clathrate is structure in which methane molecules are trapped in a web of water ice crystals. Because methane clathrate only exists at cold temperatures and high pressure, it is located mostly in undersea deposits. In 2013, Japanese scientists developed a method of extracting natural gas from offshore methane clathrate deposits.

The next alkane is ethane, C2H6. Its higher melting and boiling points (-277.6°F [-172°C] and -127.3°F [-88.5°C], respectively) reflect its larger surface area and consequently greater van der Waals attraction.

Propane, C3H8, is an important fuel because it can be liquefied at pressures low enough to be easily maintained for commercial and consumer use, allowing for easy transport and storage. Propane vaporizes to burn almost as cleanly as methane.

Higher alkanes continue the trend of increased surface area and higher melting and boiling points. However, as the number of carbon atoms increases, structural isomerism becomes possible, allowing the same molecular formula to describe two or more compounds with different structures and different physical properties. For example, Butane (C4H10) can be either a straight-chain molecule, or a branched one with three carbons in a straight chain and the fourth branching off from the middle carbon. Compounds with the same molecular formula but with different three-dimensional structures are called isomers. The straight chain isomer is called n-butane (n for "normal"), whereas the branched one is called either iso-butane, or 2-methyl propane. The latter name indicates that the longest straight-chain backbone within the molecule has three carbons (propane) and that there is a single-carbon branch (methyl) at the second position in the main chain. The extended structure of n-butane gives it a boiling point of 32°F (0°C), while the more spherical iso-butane boils at a lower temperature (10.4°F [-12°C]), due to its smaller surface area. As the number of carbons increases, so too does the number of possible isomers.

The simplest alkene is ethene, C2H4, also called ethylene. Ethene is a planar molecule, with the four hydrogen atoms splayed out in a plane and with angles between bonds of 120°. Ethene melts at -272.2°F (-169°C), and boils at -151.6°F (-102°C).

Higher alkenes take their names from the corresponding alkanes: propene, butene, pentene, and so forth. However, beginning with butene, isomerism is possible based on the position of the double bond. If the bond is between C1 and C2, the compound is 1-butene, while if it lies between C2 and C3, it is 2-butene. (The compound with a double bond between C3 and C4 is equivalent to 1-butene.) In addition, the non-rotation of the double bond means there are two structural isomers of 2-butene, one with the two terminal carbons on the same side of the C=C long axis, termed cis-2-butene, and one with the two terminal carbons on opposite sides, trans-2-butene. As might be expected, the number of possible isomers rises with an increase in number of carbons.

Alkenes have more complex and richer chemical reactions than the alkanes, due to the presence of the double bond. The most common reaction involves an addition across the double bond. For example, addition of water to ethene creates ethyl alcohol. Alkenes are often prepared by the reverse of this reaction (dehydration across the double bond).

Alkynes have a triple bond. The simplest alkyne is C2H2, athyne, also called acetylene. Acetylene is an important high-temperature fuel used especially for metal cutting.

Cyclic alkenes, such as cyclohexene (C6H10), are common solvents and also serve as starting points for a number of organic syntheses.

Benzene (C6H6) is a cyclohexane (the carbons are bonded in a ring) with three double bonds alternating around the ring. The electrons in benzene's bonds are highly delocalized, to the point that it is no longer accurate to describe them as belonging to individual carbons. Instead, they form a cloud "ring" above and below the plane of the carbons and, as a result, all the carbon-carbon bonds are of equivalent length and strength.

Scientific confirmation of global climate change has led scientists to seek out alternatives to hydrocarbon fuels, or at least to render them less polluting. In 2006, researchers from Rutgers University announced a breakthrough in coal-to-diesel fuel research. The new technology, which uses a pair of catalytic chemical reactions that selectively remove hydrogen atoms from the hydrocarbons in coal, is expected to reduce U.S. dependence on imports of foreign oil because it will enable the U.S. to transform its 286 billion tons of coal reserves into diesel fuel. The diesel fuel can then be made to power high-mileage diesel vehicles; some European diesel-powered internal combustion engines get 100 mpg (161 kpg) or more.

Also in 2006, researchers from the U.S. Department of Energy reported that they had developed a new nanostructure that acts as a catalyst that can convert hydrocarbons into less polluting fuels, as well as into other types of chemicals. The new catalyst consists of uniformly sized nanoscale cyclic tungsten trioxide clusters that line up molecule by molecule on a titanium dioxide platform. The uniform clusters enable the tungsten oxide to change directly from a solid to a gas on the platform. The reaction is efficient and has the potential to transform hydrocarbons directly into non-polluting fuel.

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Gale Document Number: GALE|CV2641950230