Alkane - Wikipedia, the free encyclopedia

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From Wikipedia, the free encyclopedia

Alkanes (also known as paraffins or saturated hydrocarbons) are chemical compounds that consist only of the elements carbon (C) and hydrogen (H) (i.e., hydrocarbons), wherein these atoms are linked together exclusively by single bonds (i.e., they are saturated compounds). Alkanes belong to a homologous series of organic compounds in which the members differ by a constant relative molecular mass of 14. Each carbon atom must have 4 bonds (either C-H or C-C bonds), and each hydrogen atom must be joined to a carbon atom (H-C bonds). A series of linked carbon atoms is known as the carbon skeleton or carbon backbone. In general, the number of carbon atoms is often used to define the size of the alkane (e.g., C2-alkane). An alkyl group, generally abbreviated with the symbol R, is a functional group or side-chain that, like an alkane, consists solely of single-bonded carbon and hydrogen atoms, for example a methyl or ethyl group.

Chemical structure of methane, the simplest alkane

The simplest possible alkane (the parent molecule) is methane, CH4. There is no limit to the number of carbon atoms that can be linked together, the only limitation being that the molecule is acyclic, is saturated, and is a hydrocarbon. Saturated oils and waxes are examples of larger alkanes where the number of carbons in the carbon backbone tends to be greater than 10. Alkanes are not very reactive and have little biological activity. Alkanes can be viewed as a molecular tree upon which can be hung the interesting biologically active/reactive portions (functional groups) of the molecule.

■ 1 Structure classification ■ 2 Isomerism ■ 3 Nomenclature ■ 3.1 Linear alkanes ■ 3.2 Branched alkanes ■ 3.3 Cyclic alkanes


Alkane - Wikipedia, the free encyclopedia

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■ 3.4 Trivial names ■ 4 Physical properties ■ 4.1 Table of alkanes ■ 4.2 Boiling point ■ 4.3 Melting point ■ 4.4 Conductivity and Solubility ■ 4.5 Molecular geometry ■ 4.6 Bond lengths and bond angles ■ 4.7 Conformation ■ 4.8 Spectroscopic properties ■ 4.8.1 Infrared spectroscopy ■ 4.8.2 NMR spectroscopy ■ 4.8.3 Mass spectrometry ■ 5 Chemical properties ■ 5.1 Reactions with oxygen (combustion reaction) ■ 5.2 Reactions with halogens ■ 5.3 Cracking ■ 5.4 Isomerization and reformation ■ 5.5 Other reactions ■ 6 Occurrence ■ 6.1 Occurrence of alkanes in the Universe ■ 6.2 Occurrence of alkanes on Earth ■ 6.3 Biological occurrence ■ 6.4 Ecological relations ■ 7 Production ■ 7.1 Petroleum refining ■ 7.2 Fischer-Tropsch ■ 7.3 Laboratory preparation ■ ■ ■ ■ ■ ■ 8 Applications 9 Environmental transformations 10 Hazards 11 See also 12 References 13 Further reading


g.734.e.Wikipedia.253.wikipedia.184 isomers. n > 3) wherein the carbon backbone splits off in one or more directions ■ cyclic (general formula CnH2n. the free encyclopedia Page 3 of 21 Structure classification Saturated hydrocarbons can be: ■ linear (general formula CnH2n + 2) wherein the carbon atoms are joined in a snake-like structure ■ branched (general formula CnH2n + in OEIS). The simplest isomer of an alkane is the one in which the carbon atoms are arranged in a single chain with no 2/21/2011 . many of which are not stable.535. neopentane C6: 5 isomers: hexane C12: 355 isomers C32: 27..[1] Saturated hydrocarbons can also combine any of the linear.411. and they are still alkanes (no general formula) as long as they are acyclic (i. n > 2) wherein the carbon backbone is linked so as to form a loop. isobutane C5: 3 isomers: pentane..770. According to the definition by IUPAC. The number of possible isomers increases rapidly with the number of carbon atoms (sequence A000602 (http://oeis. having no loops). Isomerism Alkanes with more than three carbon atoms can be arranged in numerous different ways.769 isomers C60: 22.158. forming different structural isomers.074. the former two are alkanes. This isomer is sometimes called the n-isomer (n for "normal". An isomer is like a chemical anagram. However the chain of carbon atoms may also be branched at one or more points. in which the atoms of a chemical compound are arranged or joined together in a different order. whereas the third group is called cycloalkanes. cyclic (e. although it is not necessarily the most common). http://en. polycyclic) and branching structures. isopentane. For example: ■ ■ ■ ■ ■ ■ ■ ■ ■ C1: no isomers: methane C2: no isomers: ethane C3: no isomers: propane C4: 2 isomers: n-butane.Alkane .

The first three name hydrocarbons with single.1. Unbranched. so that 1. double and triple bonds. should be as low as possible. Such compounds are called cycloalkanes.Alkane . -ine (or -yne). The members of the series (in terms of number of carbon atoms) are named as follows: methane.[2] In addition to these isomers.(for normal) where a non-linear isomer exists. Although this is not strictly implied and usually omitted from names of organic compounds with only one side-group. Chiral alkanes are of certain importance in biochemistry. o and u to create suffixes -ane. Nomenclature Main article: IUPAC nomenclature of organic chemistry Different C4-alkanes and cycloalkanes (left to right): n-butane and isobutane are the two C4H10 isomers.or 3-methylpentane.[3] August Wilhelm von Hofmann suggested systematizing nomenclature by using the whole sequence of vowels a. "-ol" represents an alcohol or OH group. This is because shorter chains attached to longer chains are prefixes and the convention includes brackets. "-one" represents a ketone. so that methoxy-methane is the IUPAC name for dimethyl ether. -ene. n-hexane or 2. Symmetric compounds will have two ways of arriving at the same carbon and four hydrogen http://en. It is difficult or impossible to find compounds with more than one IUPAC name. e. Linear alkanes Straight-chain alkanes are sometimes indicated by the prefix n.. the free encyclopedia Page 4 of 21 Branched alkanes can be chiral: 3-methylhexane and its higher homologues are chiral due to their stereogenic center at carbon atom number 3. saturated hydrocarbon chains are named systematically with a Greek numerical prefix denoting the number of carbons and the suffix "-ane". "1-" is implied in nitrooctane.g. for the hydrocarbons. the chain of carbon atoms may form one or more loops. as they occur as sidechains in chlorophyll and tocopherol (vitamin E). i. tetrahedrane (not shown) is the only C4H4 compound and has also no isomer. Chiral alkanes can be resolved into their enantiomers by enantioselective chromatography. "-oxy-" means an ether and refers to oxygen between two carbons. -une. the usage is still common in cases where there is an important difference in properties between the straight-chain and branchedchain isomers. Numbers in the name. referring to which carbon a group is attached to. CH4 .wikipedia. The IUPAC nomenclature (systematic way of naming compounds) for alkanes is based on identifying hydrocarbon 2/21/2011 . e. -one.0]butane is the only C4H6 compound and has no isomer. cyclobutane and methylcyclopropane are the two C4H8 isomers. Bicyclo[1.

with the exceptions of nonane which has a Latin prefix. For a more complete list.Alkane .org/wiki/Alkane 2/21/2011 . prefixes) order in front of the name of the root chain Comparison of nomenclatures for three isomers of C5H12 http://en.wikipedia. The key steps in the naming of more complicated branched alkanes are as follows:[5] ■ ■ ■ ■ Identify the longest continuous chain of carbon atoms Name this longest root chain using standard naming rules Name each side chain by changing the suffix of the name of the alkane from "-ane" to "-yl" Number the root chain so that sum of the numbers assigned to each side group will be as low as Ball-and-stick model of isopentane possible (common name) or 2-methylbutane ■ Number and name the side chains before the name of the root chain (IUPAC systematic name) ■ If there are multiple side chains of the same type. C6H14 . the free encyclopedia Page 5 of 21 ethane. and undecane and tridecane which have mixed-language prefixes. and neopentane.five carbon and 12 hydrogen hexane.three carbon and 8 hydrogen butane. IUPAC naming conventions can be used to produce a systematic name.six carbon and 14 hydrogen These names were derived from methanol. Alkanes with five or more carbon atoms are named by adding the suffix -ane to the appropriate numerical multiplier prefix[4] with elision of any terminal vowel (-a or -o) from the basic numerical term. ether.four carbon and 10 hydrogen pentane. C4H10 . respectively. and number each one. pentane. see List of alkanes. Hence. etc. C3H8 . heptane. Branched alkanes Simple branched alkanes often have a common name using a prefix to distinguish them from linear alkanes. C7H16. for example n-pentane.two carbon and six hydrogen propane. C8H18. hexane. octane. C5H12 . C5H12. C2H6 . propionic acid and butyric acid.Wikipedia. C6H14. use prefixes such as "di-" and "tri-" to indicate it as such. ■ Add side chain names in alphabetical (disregarding "di-" etc. The prefix is generally Greek. isopentane.

wikipedia. Substituted cycloalkanes are named similar to substituted alkanes — the cycloalkane ring is stated. e. in the technical sense. with the numbering decided by Cahn-Ingold-Prelog rules." Together.Alkane .g. but they are joined up in a five-membered ring. The use of the term "paraffin" is a general term and often does not distinguish between a pure compounds and mixtures of isomers with the same chemical formula (i. butane and cyclobutane. Simple cycloalkanes have a prefix "cyclo-" to distinguish them from alkanes.[4] Trivial names The trivial (non-systematic) name for alkanes is "paraffins. etc. It is almost certain that the term paraffin stems from the petrochemical industry.Wikipedia. 2/21/2011 . not alkanes. Cycloalkanes are also called naphthenes..2-dimethylpropane Cyclic alkanes Main article: Cycloalkane So-called cyclic alkanes are. cyclopentane (C5H10) is a cycloalkane with 5 carbon atoms just like pentane (C5H12). propane and cyclopropane. They were coined before the development of systematic names. the free encyclopedia Page 6 of 21 Common name IUPAC name Structure n-pentane pentane isopentane neopentane 2-methylbutane 2. pentane and isopentane. Examples The following trivial names are retained in the IUPAC system: ■ isobutane for 2-methylpropane http://en. like a chemical anagram).. In a similar manner. Branched-chain alkanes are called isoparaffins. and have been retained due to familiar usage in industry. but contain one or more rings. They are hydrocarbons just like alkanes.g. alkanes are known as the paraffin series. Cycloalkanes are named as per their acyclic counterparts with respect to the number of carbon atoms.e. Trivial names for compounds are usually historical artifacts. but cycloalkanes. and the substituents are according to their position on the ring..

749(liquid) solid solid solid solid Tetracontane C40H82 Pentacontane C50H102 Boiling point http://en.703(liquid) 0.wikipedia. the free encyclopedia Page 7 of 21 ■ isopentane for 2-methylbutane ■ neopentane for 2.684(liquid) 0.740(liquid) 0.Alkane .626(liquid) 0.Wikipedia.659(liquid) 0. Physical properties Table of alkanes Alkane Methane Ethane Propane Butane Pentane Hexane Heptane Octane Nonane Decane Undecane Dodecane Icosane Triacontane Formula Boiling point [°C] Melting point [°C] Density [g·cm3] (at 20°C) CH4 C2H6 C3H8 C4H10 C5H12 C6H14 C7H16 C8H18 C9H20 C10H22 C11H24 C12H26 C20H42 C30H62 -162 -89 -42 0 36 69 98 126 151 174 196 216 343 450 525 575 -183 -172 -188 -138 -130 -95 -91 -57 -54 -30 -26 -10 37 66 82 91 gas gas gas gas 0.730(liquid) 2/21/2011 .2-dimethylpropane.718(liquid) 0.

2-dimethylbutane. the boiling point rises 20 . two molecules 2.[6] There are two determinants for the strength of the van der Waals forces: ■ the number of electrons surrounding the molecule.30 °C for each carbon added to the chain. thus the greater van der Waals forces. Thus the better put together solid structures will require more energy to break apart. and 2.[citation needed] Melting point The melting points of the alkanes follow a similar trend to boiling points for the same reason as outlined above. the free encyclopedia Page 8 of 21 Alkanes experience inter-molecular van der Waals forces. As the boiling point of alkanes is primarily determined by weight. hence the greater van der Waals forces. and after C18H38 they are solids.3-dimethylbutane can "lock" into each other better than the cross-shaped 2. For alkanes. this can be seen from the graph above (i. compare isobutane (2-methylpropane) and n-butane (butane).org/wiki/Alkane 2/21/2011 . Stronger inter-molecular van der Waals forces give rise to greater boiling points of alkanes. from CH4 to C4H10 alkanes are gaseous. it should not be a surprise that the boiling point has almost a linear relationship with the size (molecular weight) of the molecule. That is. which give a plane of intermolecular contact. cycloalkanes tend to have higher boiling points than their linear counterparts due to the locked conformations of the molecules. which requires more energy to break apart.[7] http://en. between adjacent molecules.3-dimethylbutane which boil at 50 and 58 °C. the blue line). Solids have more rigid and fixed structure than liquids. The odd-number alkanes pack less well and so the "looser" organized solid packing structure requires less energy to break apart.Wikipedia.e. This is because even numbered alkanes pack well in the solid phase.Alkane .[6] For the latter case. from C5H12 to C17H36 they are liquids. which boil at -12 and 0 °C.[6] Melting (blue) and boiling (pink) points of the first 14 n-alkanes in °C. On the other hand. For example. There is one significant difference between boiling points and melting points.. (all other things being equal) the larger the molecule the higher the melting point. The odd-numbered alkanes have a lower trend in melting points than even numbered alkanes.2-dimethylbutane and 2. forming a well-organized structure. respectively. this rule applies to other homologous series.wikipedia. This rigid structure requires energy to break down. As a rule of thumb. A straight-chain alkane will have a boiling point higher than a branched-chain alkane due to the greater surface area in contact. which increases with the alkane's molecular weight ■ the surface area of the molecule Under standard conditions.

Hence. miscible in all proportions among themselves. which often have melting points higher than those of the linear analogues.Alkane . http://en. which have identical energies. Since the hydrogen bonds between individual water molecules are aligned away from an alkane molecule. again depending on the ability of the alkane in question to packing well in the solid phase: This is particularly true for isoalkanes (2-methyl isomers). for example. The density of the alkanes usually increases with increasing number of carbon atoms. The carbon atoms in alkanes are always sp3 hybridized. Their solubility in nonpolar solvents is relatively good. It is derived from the electron configuration of carbon.47° between them. the coexistence of an alkane and water leads to an increase in molecular order (a reduction in entropy). The former result from the overlap of a sp³-orbital of carbon with the 1s-orbital of a hydrogen. a property that is called lipophilicity. For this reason they do not form hydrogen bonds and are insoluble in polar solvents such as water.09×10−10 m for a C – H bond and 1. but remains less than that of water.wikipedia. nor are they substantially polarized by an electric field. As there is no significant bonding between water molecules and alkane molecules. which has four valence electrons. Molecular geometry The molecular structure of the alkanes directly affects their physical and chemical characteristics. sp3-hybridization in methane. Conductivity and Solubility Alkanes do not conduct electricity. alkanes form the upper layer in an alkane-water mixture. are arranged spatially in the form of a tetrahedron. the free encyclopedia Page 9 of 21 The melting points of branched-chain alkanes can be either higher or lower than those of the corresponding straight-chain alkanes. that is to say that the valence electrons are said to be in four equivalent orbitals derived from the combination of the 2s orbital and the three 2p orbitals. the latter by the overlap of two sp³-orbitals on different carbon atoms.Wikipedia. the second law of thermodynamics suggests that this reduction in entropy should be minimized by minimizing the contact between alkane and water: Alkanes are said to be hydrophobic in that they repel 2/21/2011 . the angle of cos−1(−⅓) ≈ 109.54×10−10 m for a C – C bond. These orbitals. Different alkanes are. The bond lengths amount to 1. Bond lengths and bond angles An alkane molecule has only C – H and C – C single bonds.

with the antiperiplanar conformation always being the most favored around each carbon-carbon 2/21/2011 . the free encyclopedia Page 10 of 21 The spatial arrangement of the bonds is similar to that of the four sp³-orbitals—they are tetrahedrally arranged. one will see the so-called Newman projection. is low compared to the thermal energy of an ethane molecule at ambient temperature.wikipedia.Wikipedia. If one looks down the axis of the C – C bond. Despite this apparent freedom. This is a consequence of the free rotation about a carbon – carbon single bond. resulting from the projection of the base of the tetrahedron onto a flat plane. Conformation Main article: Alkane stereochemistry The structural formula and the bond angles are not usually sufficient to completely describe the geometry of a molecule. do not correspond with the reality. Ball-and-stick models of the two rotamers of ethane http://en.47° between them. However. the torsion angle between a given hydrogen atom attached to the front carbon and a given hydrogen atom attached to the rear carbon can vary freely between 0° and 360°. Structural formulae that represent the bonds as being at right angles to one another.Alkane . equivalent to the rotation of one CH3-group by 120° relative to the other. There is a further degree of freedom for each carbon – carbon bond: the torsion angle between the atoms or groups bound to the atoms at each end of the bond. with an angle of 109. also known as rotamers.6 kJ/mol lower in energy (more stable) than the eclipsed conformation (the least stable). There is constant rotation about the C-C bond. For this reason. differ in energy: The staggered conformation is 12. The two conformations. Ethane forms the simplest case for studying the conformation of alkanes. staggered on the right. The actual structure will always The tetrahedral structure of methane. The time taken for an ethane molecule to pass from one staggered conformation to the next. is of the order of 10−11 seconds. Newman projections of the two conformations of ethane: eclipsed on the left. only two limiting conformations are important: eclipsed conformation and staggered conformation. alkanes are usually shown in a zigzag arrangement in diagrams or in models. while both common and useful. known as the torsion energy. This difference in energy between the two conformations. The case of higher alkanes is more complex but based on similar principles. The hydrogen atoms on both the front and rear carbon atoms have an angle of 120° between them. as there is only one C – C bond. The spatial arrangement described by the torsion angles of the molecule is known as its conformation.

5. Mass spectrometry Alkanes have a high ionization energy. whatever the models may suggest. Unlike most other organic compounds. in the case of branched chain alkanes. and therefore for the absence of other characteristic spectroscopic features. The carbon–hydrogen bending modes depend on the nature of the group: methyl groups show bands at 1450 cm−1 and 1375 cm−1.Wikipedia. they possess no functional groups. but. 15 – 55 (secondary. and other fragment are often spaced by intervals of fourteen mass units. while the carbon–carbon stretching mode absorbs between 800 and 1300 cm−1. because their C bonds are relatively stable and cannot be easily broken. methylene. NMR spectroscopy The proton resonances of alkanes are usually found at δH = 0. http://en. 20 – 60 (tertiary. alkanes show a relatively low reactivity. and can be missed in weak samples. The fragmentation pattern can be difficult to interpret. Infrared spectroscopy The carbon–hydrogen stretching mode gives a strong absorption between 2850 and 2960 cm−1.wikipedia. The carbon-13 resonance of quaternary carbon atoms is characteristically weak.5 – 1. C-H) and quaternary. Chemical properties In general. Carbon chains with more than four carbon atoms show a weak absorption at around 725 cm−1. methyne. Alkanes are notable for having no other groups. corresponding to sequential loss of CH2-groups.Alkane . and the molecular ion is usually weak. The fragment resulting from the loss of a single methyl group (M−15) is often absent. and so show some of the features of alkanes in their spectra. or sample that have not been run for a sufficiently long time. the carbon chain is preferentially cleaved at tertiary or quaternary carbons due to the relative stability of the resulting free radicals. as the differences in energy between the conformations are small compared to the thermal energy of the molecules: Alkane molecules have no fixed structural form. due to the lack of Nuclear Overhauser effect and the long relaxation time. while methylene groups show bands at 1465 cm−1 and 1450 cm− 2/21/2011 . -CH2-). The carbon-13 resonances depend on the number of hydrogen atoms attached to the carbon: δC = 8 – 30 (primary. -CH3). methyl. Spectroscopic properties Virtually all organic compounds contain carbon – carbon and carbon – hydrogen bonds. the free encyclopedia Page 11 of 21 differ somewhat from these idealized forms.

wikipedia.5)O2 → (n+1)H2O + nCO2 In the absence of sufficient oxygen. and so can be seen to be somewhat more stable.5O2 → CO + 2H2O See the alkane heat of formation table for detailed data. carbon monoxide or even soot can be formed. molecules with unpaired electrons.5°) in order to allow the different groups sufficient space. such as cracking and reformation where longchain alkanes are converted into shorter-chain alkanes and straight-chain alkanes into branched-chain isomers. Free radicals. known as steric hindrance. in the case of methane. In highly branched alkanes. and can substantially increase the reactivity. the free encyclopedia Page 12 of 21 They react only very poorly with ionic or other polar substances.Wikipedia. for alkanes increases by about 650 kJ/mol per CH2 group. and bind 2/21/2011 . In addition.Alkane . The general equation for complete combustion is: CnH2n+2 + (1. certain transition metal complexes in (See: carbon-hydrogen bond activation). with halogens. This causes a tension in the molecule. are possible as the carbon atoms are in a strongly reduced condition. as shown below: CnH(2n+2) + nO2 → (n+1)H2O + nCO For example methane: 2CH4 + 3O2 → 2CO + 4H2O CH4 + 1. play a large role in most reactions of alkanes. alkanes have been shown to interact with. in particular with oxygen and the halogens. Branched-chain alkanes have lower values of ∆cHo than straight-chain alkanes of the same number of carbon atoms. The acid dissociation constant (pKa) values of all alkanes are above 60. http://en.5n+0. Reaction with oxygen (if an amount of the least is enough to meet the reaction stoichometry) leads to combustion without any smoke. However redox reactions of alkanes. the bond angle may differ significantly from the optimal value (109. substitution. The standard enthalpy change of combustion. ∆cHo. although they become increasingly difficult to ignite as the number of carbon atoms increases. This inertness is the source of the term paraffins (with the meaning here of "lacking affinity"). the lowest possible oxidation state for carbon (−4) is reached. Reactions with oxygen (combustion reaction) All alkanes react with oxygen in a combustion reaction. In crude oil the alkane molecules have remained chemically unchanged for millions of years. hence they are practically inert to acids and bases (see: carbon acids). 2/21/2011 . The mixture produced. The hydrogen atoms of the alkane are progressively replaced by halogen atoms.Alkane . ■ Chain termination where step the radicals recombine. These reactions are an important industrial route to halogenated hydrocarbons. ■ Chain reaction or Propagation then takes place—the halogen radical abstracts a hydrogen from the alkane to give an alkyl radical. which usually leads to a mixture of products. There are three steps: ■ Initiation the halogen radicals form by homolysis. energy in the form of heat or light is required.wikipedia. indicating that all hydrogen atoms are susceptible to reaction. the Statistical Distribution should be 25% and 75%] Cracking Main article: Cracking (chemistry) http://en.Wikipedia. and can lead to an explosion. is not a statistical mixture: Secondary and tertiary hydrogen atoms are preferentially replaced due to the greater stability of secondary and tertiary free-radicals. the free encyclopedia Page 13 of 21 Reactions with halogens Main article: Free radical halogenation Alkanes react with halogens in a so-called free radical halogenation reaction. An example can be seen in the monobromination of propane:[6] [In the Figure below. This reacts further. The reaction is highly exothermic. Free-radicals are the reactive species that participate in the reaction. Experiments have shown that all halogenation produces a mixture of all possible isomers. Usually.

This can be done with a thermal or catalytic method. The thermal cracking process follows a homolytic mechanism with formation of free-radicals. Isomerization and reformation Isomerization and reformation are processes in which straight-chain alkanes are heated in the presence of a platinum 2/21/2011 . and thus they proceed by a self-propagating chain mechanism.. which indicate that Titan's atmosphere periodically rains liquid methane onto the moon's surface. the alkanes become cycloalkanes or aromatic hydrocarbons. Both of these processes raise the octane number of the substance. the free encyclopedia Page 14 of 21 Cracking breaks larger molecules into smaller ones. 0.5 ppm ethane).e. The chain of reactions is eventually terminated by radical or ion recombination. Uranus (1.wikipedia. In both types of processes. the corresponding reactive intermediates (radicals.5% methane. http://en.0005% ethane).2% methane. which promote a heterolytic (asymmetric) breakage of bonds yielding pairs of ions of opposite charges. Titan (1.Wikipedia. There also appear to be Methane/Ethane lakes near the north polar regions of Titan.and intermolecular hydrogen transfer or hydride transfer. Carbon-localized free-radicals and cations are both highly unstable and undergo processes of chain rearrangement. chlorine and light convert hydrocarbons to sulfonyl chlorides. 0. giving off hydrogen as a by-product.[8] Also on Titan. In the Reed reaction. cracking) and intra.0002% ethane).00025% ethane) and Neptune (1. as discovered by Cassini's radar imaging. The fermentation of alkanes to carboxylic acids is of some technical importance. a methane-spewing volcano was spotted and this volcanism is believed to be a significant source of the methane in the atmosphere. usually a carbocation and the very unstable hydride anion.99% methane. Methane and ethane have also been detected in the tail of the comet Hyakutake.Alkane . the alkanes become branched-chain isomers. Occurrence Occurrence of alkanes in the Universe Alkanes form a small portion of the atmospheres of the outer gas planets such as Jupiter (0. sulfur dioxide. a satellite of Saturn. Alkanes can be chlorosulfonated and nitrated.1% methane. although both reactions require special conditions. was examined by the Huygens probe. 1. The catalytic cracking process involves the presence of acid catalysts (usually solid acids such as silica-alumina and zeolites). In reformation. 0. C-C scission in position beta (i. ions) are permanently regenerated.6% methane). Other reactions Alkanes will react with steam in the presence of a nickel catalyst to give hydrogen. Saturn (0. In isomerization.

the amount of combustible energy of the known methane hydrate fields exceeds the energy content of all the natural gas and oil deposits put together[citation needed]. which would have evaporated these volatile molecules.Alkane . away from the Sun. The depletion of these hydrocarbons is the basis for what is known as the energy crisis.g. produced by animals and decaying matter. Natural gas resulted thereby for example from the following reaction: C6H12O6 → 3CH4 + 3CO2 Methane and ethane make up a tiny proportion of Jupiter's atmosphere Extraction of oil. the free encyclopedia Page 15 of 21 Chemical analysis showed that the abundances of ethane and methane were roughly equal. which is a possible renewable energy source. Methane is also present in what is called biogas. have formed over millions of years and once exhausted cannot be readily replaced.[citation needed] The most important commercial sources for alkanes are natural gas and oil. however.[citation needed] Although this cannot be commercially exploited at the present time.wikipedia. Occurrence of alkanes on Earth Traces of methane gas (about 0. methane can co-crystallize with water to form a solid methane hydrate. Solid alkanes are known as tars and are formed when more volatile alkanes such as gases and oil evaporate from hydrocarbon deposits. located beneath an impermeable cap rock and so are trapped. at high pressures and low temperatures (such as at the bottom of the oceans). with some propane and butane: oil is a mixture of liquid alkanes and other hydrocarbons. which is thought to imply that its ices formed in interstellar space. Alkanes have a low solubility in 2/21/2011 . http://en. One of the largest natural deposits of solid alkanes is in the asphalt lake known as the Pitch Lake in Trinidad and Tobago.[9] Alkanes have also been detected in meteorites such as carbonaceous chondrites. found for example in the gut of cows. which contains many different hydrocarbons including alkanes These hydrocarbons collected in porous rocks.methane extracted from methane hydrate is considered therefore a candidate for future fuels.0001% or 1 ppm) occur in the Earth's atmosphere. oil fields. These hydrocarbons were formed when dead marine animals and plants (zooplankton and phytoplankton) died and sank to the bottom of ancient seas and were covered with sediments in an anoxic environment and converted over many millions of years at high temperatures and high pressure to their current form.Wikipedia. so the content in the oceans is negligible. e. produced primarily by organisms such as Archaea.[6] Natural gas contains primarily methane and ethane. These deposits..

the methanogens. [citation needed] In plants. which can release up to 150 liters per day. with carbon being released back into the atmosphere after having been fixed by photosynthesis. The methane output of cattle and other herbivores. at the end of the carbon cycle. and protect against bacteria.. They also produce this simplest of all alkanes in the intestines of humans. extracted from deer of the family Moschidae. It is probable that our current deposits of natural gas were formed in a similar way. if a minor role.g. in the biology of the three eukaryotic groups of organisms: fungi.[citation needed] is also due to methanogens.. but are only rarely major constituents. Rhodotorula sp.wikipedia. hence. and release about two billion tonnes of Methanogenic archaea in the gut of methane per year[citation needed]—the atmospheric content of this gas is produced nearly exclusively by this cow are responsible for some of them. Bacteria and archaea Certain types of bacteria can metabolize alkanes: they prefer even-numbered carbon chains as they are easier to degrade than odd-numbered chains. fungi. e. Pichia sp. can use alkanes as a source of carbon and/or energy..[citation needed] All further information refers to (acyclic) alkanes.[citation needed] Fungi and plants Alkanes also play a role. the methane in Earth's atmosphere. The energy is released by the oxidation of hydrogen: CO2 + 4H2 → CH4 + 2H2O Methanogens are also the producers of marsh gas in wetlands. and harmful insects. between twenty-seven and thirty-three carbon atoms http://en. The carbon chains in plant alkanes are usually odd-numbered. certain archaea. and can cause serious problems for aircraft in tropical regions. produce large quantities of methane by the metabolism of carbon dioxide or other oxidized organic compounds.[citation needed] On the other hand. Some specialized yeasts. they do not rank biologically among the essential materials. Candida tropicale. plants and animals. the solid long-chain alkanes are found in the plant cuticle and epicuticular wax of many species. Cycloalkanes with 14 to 18 carbon atoms occur in musk.[10] They protect the plant against water loss. Methanogenic archaea are. The fungus Amorphotheca resinae prefers the longer-chain alkanes in aviation fuel. [citation needed] and of termites. prevent the leaching of important minerals by the rain. the free encyclopedia Page 16 of 21 Biological occurrence Although alkanes occur in nature in various way.Alkane .org/wiki/Alkane 2/21/2011 .Wikipedia.

org/wiki/Alkane 2/21/2011 .14-tetramethylpentadecane. One example is the shark liver oil. is the ecological relationship between the sand bee (Andrena nigroaenea) and the early spider orchid (Ophrys sphegodes). [citation needed] Animals Alkanes are found in animal products. the free encyclopedia Page 17 of 21 in length[10] and are made by the plants by decarboxylation of even-numbered fatty acids. 3-methylpentaicosane (C26H54) and 9-methylpentaicosane (C26H54). and acts by smell over longer distances. 17. The orchid takes advantage of this mating arrangement to get the male bee to collect and disseminate its pollen. chemical messenger materials.Wikipedia. a useful characteristic for pest control.Alkane . With others like the tsetse fly Glossina morsitans morsitans. the pheromone contains the four alkanes 2methylheptadecane (C18H38). C19H40). which is approximately 14% pristane (2. 15. but also produce large quantities of the three alkanes in the same ratio as female sand bees. the females emit a mixture of tricosane (C23H48).[11] Ecological relations One example. Production Petroleum refining Early spider orchid (Ophrys sphegodes) http://en. The exact composition of the layer of wax is not only species-dependent.[citation needed] Their occurrence is more important in pheromones. they are transferred by body contact. although they are less important than unsaturated hydrocarbons.19.23trimethylheptatriacontane (C40H82). Sand bees use pheromones in order to identify a mate. temperature or humidity.21-dimethylheptatriacontane (C39H80).[citation needed] Waggledancing honeybees produce and release two alkanes.wikipedia. parts of its flower not only resemble the appearance of sand bees. and males are attracted by specifically this odor. the latter is dependent for pollination on the former. in which both plant and animal alkanes play a role. it allows the orchid to transfer its pollen. primarily pentacosane (C25H52). as the support beetle Xylotrechus colonus.19-dimethylheptatriacontane (C39H80) and 15. As a result numerous males are lured to the blooms and attempt to copulate with their imaginary partner: although this endeavor is not crowned with success for the bee. tricosane and pentacosane. With some kinds. but changes also with the season and such environmental factors as lighting conditions.6.10. on which above all insects are dependent for communication. pentacosane (C25H52) and heptacosane (C27H56) in the ratio 3:3:1. nigroaenea. which will be dispersed after the departure of the frustrated male to different blooms. in the case of A.

Laboratory preparation An oil refinery at Martinez. alkanes are generally non-reactive chemically or biologically. the best-known methods are hydrogenation of alkenes: RCH=CH2 + H2 → RCH2CH3 (R = alkyl) Alkanes or alkyl groups can also be prepared directly from alkyl halides in the Corey-House-Posner-Whitesides reaction. The BartonMcCombie deoxygenation[12][13] removes hydroxyl groups from alcohols e.Alkane .[6] Alkanes are separated in an oil refinery by fractional distillation and processed into many different products. There is usually little need for alkanes to be synthesized in the laboratory. For example. n-butane as a side-product: C4H9Li + H2O → C4H10 + LiOH However. This method is used to produce substitutes for petroleum distillates. the free encyclopedia Page 18 of 21 As stated earlier.Wikipedia. it gives ethanol. at times it may be desirable to make a portion of a molecule into an alkane like functionality (alkyl group) using the above or similar methods. which is not an alkane. Also. it is often a side-product of a reaction. when this is attached to a hydroxy group. since they are usually commercially available. and the Clemmensen reduction[14][15][16][17] removes carbonyl groups from aldehydes and ketones to form alkanes or alkyl-substituted compounds e.g. When alkanes are produced in the laboratory. California. the use of nbutyllithium as a strong base gives the conjugate acid. including alkanes.g. For example.wikipedia. an ethyl group is an alkyl group. To do so. and do not undergo functional group interconversions cleanly. from carbon monoxide and 2/21/2011 . Fischer-Tropsch The Fischer-Tropsch process is a method to synthesize liquid hydrocarbons. the most important source of alkanes is natural gas and crude oil.: http://en.

In latter function.2. which causes knocking. The first four alkanes are used mainly for heating and cooking purposes. Propane. Alkanes from nonane 2/21/2011 . the middle alkanes are also good solvents for nonpolar substances.Alkane . the higher melting points of these alkanes can cause problems at low temperatures and in polar regions. hexadecane (an alkane with sixteen carbon atoms) are liquids of higher viscosity. Many solid alkanes find use as paraffin wax. they work at the same time as anti-corrosive agents. used.Wikipedia. and in some countries for electricity generation. for example. in road surfacing. The two alkanes are used as propellants in aerosol sprays. They are used as fuels in internal combustion engines. They form instead the major part of diesel and aviation fuel. http://en. in candles. is used in the propane gas burner. cetane being an old name for hexadecane. It is. Alkanes with a chain length of approximately 35 or more carbon atoms are found in bitumen. However. than their straight-chain homologues. which consists primarily of esters. less and less suitable for use in gasoline. easier to transport them as liquids: This requires both compression and cooling of the gas. Diesel fuels are characterized by their cetane number. Methane and ethane are the main components of natural gas. This should not be confused however with true wax. as they vaporise easily on entry into the combustion chamber without forming droplets. the higher alkanes have little value and are usually split into lower alkanes by cracking. Propane and butane can be liquefied at fairly low pressures. However. for example. which would impair the uniformity of the combustion. and billions of kilograms of these materials are made and used each year. From pentane to octane the alkanes are reasonably volatile liquids. and are well known as liquified petroleum gas (LPG). butane in disposable cigarette lighters. Alkanes from hexadecane upwards form the most important components of fuel oil and lubricating oil. Apart from their use as fuels.4-trimethylpentane (isooctane) has an arbitrary value of 100. where the fuel becomes too thick to flow correctly. they are normally stored as gases under pressure. the free encyclopedia Page 19 of 21 Applications The applications of a certain alkane can be determined quite well according to the number of carbon atoms. for example.wikipedia. This propensity to premature ignition is measured by the octane rating of the fuel. Some synthetic polymers such as polyethylene and polypropylene are alkanes with chains containing hundreds of thousands of carbon atoms. as their hydrophobic nature means that water cannot reach the metal surface. Branched-chain alkanes are preferred as they are much less prone to premature ignition. for instance. however. These materials are used in innumerable applications. and heptane has a value of zero. where 2.

http://en.acdlabs. although this risk decreases with the length of the carbon chain.iupac. U. See also ■ ■ ■ ■ Alkene Alkyne Cycloalkane Basketane References 1. The straight-chain isomer of hexane is a neurotoxin. ^ Meierhenrich. http://www.htm. A Guide to IUPAC Nomenclature of Organic Compounds (Recommendations 1993).1: Hydrocarbons" (http://www. hexane. ^ IUPAC. by oxidizing the terminal carbon atom. Compendium of Chemical Terminology.msu. 4. and octane are classed as dangerous for the environment and harmful.wikipedia. However. . ^ a b William Reusch.Wikipedia. Online corrected version: (2006-) "alkanes (http://goldbook. Amino Acids and the Asymmetry of Life (http://www. The resulting fatty acid could be metabolized through the fatty acid degradation pathway. (the "Gold Book") (1997). "Nomenclature .cem. Retrieved 12 February 2007. http://www. "R-2. like chloroform. The product is an alcohol. because they have no functional groups (like hydroxyl or carbonyl) that are needed by most organisms in order to metabolize the compound. (2008).htm. the free encyclopedia Page 20 of 21 Environmental transformations When released in the environment. Virtual Textbook of Organic Chemistry.msu. Halogen-rich alkanes. Other lower alkanes can also form explosive mixtures with air. that could be next oxidized to an aldehyde. 3. alkanes don't undergo rapid biodegradation.Alkane .htm) .org/ and finally to a carboxylic acid. Commission on Nomenclature of Organic Chemistry (1993). Blackwell Scientific. 2. Springer. can be carcinogenic as well. heptane.2.cem. ISBN 978-3-540-76885-2. Hazards Methane is explosive when mixed with air (1 – 8% CH4).edu/~reusch/VirtualText/ ".com/chemistry/organic/book/978-3-540-76885-2. The lighter liquid alkanes are highly 2/21/2011 . Pentane.springer. ^ IUPAC.acdlabs.htm) . 2nd ed. Retrieved 18 October 2008.Alkanes" (http://www. some bacteria can metabolize some alkanes (especially those linear and short).springer.

ncbi. P. 1574-1585 13. Syn. ^ Barton. Kaminski.1126%2Fscience. ^ Boese R. ^ a b EA Baker (1982) Chemistry and morphology of plant epicuticular waxes. ^ 2/21/2011 . Rev.1371/ Weiss . KL Alvin and CE Price. 22.3.pbio. Perkin Trans. ^ Mumma. ^ Titan: Arizona in an Icebox? (http://www.3. K.msu. No.1002%2F%28SICI%291521-3773%2819990401%2938%3A7%3C988%3A%3AAID-ANIE988% 3E3. edited by DF Cutler. e228 doi:10.htm) http://en.wikipedia. 8. Rev.X. doi:10. G. dello Russo. J. M.nlm.1371/journal.msu. ^ Yamamura.1310) . McCombie. 7. 1942.Alkane . 21 January 2004. 1969.272. 1975.cem.. 5. M. Quart. (21 August 2007) The Scent of the Waggle Dance. http://www. (Review) 15. doi:10.cem. 1 1975. React. Boyd (1992).edu/~reusch/VirtualText/nomexmp1. J. 401..planetary.2-S (http://dx. 16. Along with Carbon Monoxide and Water.0050228) 12.. Blaser D (1999). London... Science 272 (5266): 1310. (Review) 16. M. verified 28 March 2005 9. New Jersey: Prentice Hall. "Examples of the IUPAC Rules in Practice" (http://www. D. Morrison. St.272. the free encyclopedia Page 21 of 21 5. Academic Press. ISBN 0-13-643669-2.cem. Xie (1996). Disanti. 1989. E. N. ^ Vedejs. Nishiyama.D. Chem.doi.plosjournals. PMID 8650540 (http://www. Emily Lakdawalla. 8. Soc. 6.htm) . 1991. ^ a b c d e f R. Magee-Sauer. "The melting point alternation in the short-chain n-alkanes: Single-crystal X-ray analyses of propane at 30 K and of n-butane to n-nonane at 90 K". Org. 89.CO. Organic Chemistry (6th ed. L. and D. T.0050228 [1] (http://biology. 14. E. S. pp139-165.. D. C. ^ Crich.).Wikipedia. Virtual Textbook of Organic Chemistry. L. ^ Martin. Fomenkova. 522. S. ISBN 0 12 199920 3 11. 1..html) . 23. 309-313. 155.. ^ Thom et al. H. Woodgate. 1413-1432. Vol. Org. PLoS Biology. "Detection of Abundant Ethane and Methane. ^ William Reusch. N.nih.1310 (http://dx. R. Chem. Quintero. React. Angew Chemie Int Ed 38: 988–992. In "The Plant Cuticle".A.. (Review) 17. 9..(Review) Further reading ■ Virtual Textbook of Organic Chemistry (<988::AIDANIE988>3.J. W.doi.htm. R. Comp. in Comet C/1996 B2 Hyakutake: Evidence for Interstellar Origin".CO%3B2-S) . S.

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