Hydrocarbon - wikipedia Hydrocarbon Ball - and - stick model of the methane molecule, CH. Methane is part of a homologous series known as the alkanes, which contain single bonds only. In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon, and thus are group 14 hydrides. Hydrocarbons, from which one hydrogen atom has been removed, are functional groups called hydrocarbyls. Aromatic hydrocarbons ( arenes ), alkanes, cycloalkanes and alkyne - based compounds are different types of hydrocarbons. Most hydrocarbons found on Earth naturally occur in crude oil, where decomposed organic matter provides an abundance of carbon and hydrogen which, when bonded, can catenate to form seemingly limitless chains. Contents 1 Types of hydrocarbons 1.1 General properties 1.2 Simple hydrocarbons and their variations 2 Usage 3 Poisoning 4 Reactions 4.1 Substitution reactions 4.2 Addition reactions 4.3 Combustion 4.3. 1 Petroleum 4.3. 2 Bioremediation 5 Safety 6 Environmental impact 7 See also 8 References 9 Bibliography 10 External links Types of hydrocarbons The classifications for hydrocarbons, defined by IUPAC nomenclature of organic chemistry are as follows : Saturated hydrocarbons are the simplest of the hydrocarbon species. They are composed entirely of single bonds and are saturated with hydrogen. The formula for acyclic saturated hydrocarbons ( i.e., alkanes ) is C H. The most general form of saturated hydrocarbons is C H, where r is the number of rings. Those with exactly one ring are the cycloalkanes. Saturated hydrocarbons are the basis of petroleum fuels and are found as either linear or branched species. Substitution reaction is their characteristics property ( like chlorination reaction to form chloroform ). Hydrocarbons with the same molecular formula but different structural formulae are called structural isomers. As given in the example of 3 - methylhexane and its higher homologues, branched hydrocarbons can be chiral. Chiral saturated hydrocarbons constitute the side chains of biomolecules such as chlorophyll and tocopherol. Unsaturated hydrocarbons have one or more double or triple bonds between carbon atoms. Those with double bond are called alkenes. Those with one double bond have the formula C H ( assuming non-cyclic structures ). Those containing triple bonds are called alkyne. Those with one triple bond have the formula C H. Aromatic hydrocarbons, also known as arenes, are hydrocarbons that have at least one aromatic ring. Hydrocarbons can be gases ( e.g. methane and propane ), liquids ( e.g. hexane and benzene ), waxes or low melting solids ( e.g. paraffin wax and naphthalene ) or polymers ( e.g. polyethylene, polypropylene and polystyrene ). General properties Because of differences in molecular structure, the empirical formula remains different between hydrocarbons ; in linear or `` straight - run '' alkanes, alkenes and alkynes, the amount of bonded hydrogen lessens in alkenes and alkynes due to the `` self - bonding '' or catenation of carbon preventing entire saturation of the hydrocarbon by the formation of double or triple bonds. This inherent ability of hydrocarbons to bond to themselves is known as catenation, and allows hydrocarbons to form more complex molecules, such as cyclohexane, and in rarer cases, arenes such as benzene. This ability comes from the fact that the bond character between carbon atoms is entirely non-polar, in that the distribution of electrons between the two elements is somewhat even due to the same electronegativity values of the elements ( ~ 0.30 ), and does not result in the formation of an electrophile. Generally, with catenation comes the loss of the total amount of bonded hydrocarbons and an increase in the amount of energy required for bond cleavage due to strain exerted upon the molecule ; in molecules such as cyclohexane, this is referred to as ring strain, and occurs due to the `` destabilized '' spatial electron configuration of the atom. In simple chemistry, as per valence bond theory, the carbon atom must follow the `` 4 - hydrogen rule '', which states that the maximum number of atoms available to bond with carbon is equal to the number of electrons that are attracted into the outer shell of carbon. In terms of shells, carbon consists of an incomplete outer shell, which comprises 4 electrons, and thus has 4 electrons available for covalent or dative bonding. Hydrocarbons are hydrophobic like lipids. Some hydrocarbons also are abundant in the solar system. Lakes of liquid methane and ethane have been found on Titan, Saturn 's largest moon, confirmed by the Cassini - Huygens Mission. Hydrocarbons are also abundant in nebulae forming polycyclic aromatic hydrocarbon ( PAH ) compounds. Simple hydrocarbons and their variations Number of carbon atoms Alkane ( single bond ) Alkene ( double bond ) Alkyne ( triple bond ) Cycloalkane Alkadiene Methane -- -- -- -- Ethane Ethene ( ethylene ) Ethyne ( acetylene ) -- -- Propane Propene ( propylene ) Propyne ( methylacetylene ) Cyclopropane Propadiene ( allene ) Butane Butene ( butylene ) Butyne Cyclobutane Butadiene 5 Pentane Pentene Pentyne Cyclopentane Pentadiene ( piperylene ) 6 Hexane Hexene Hexyne Cyclohexane Hexadiene 7 Heptane Heptene Heptyne Cycloheptane Heptadiene 8 Octane Octene Octyne Cyclooctane Octadiene 9 Nonane Nonene Nonyne Cyclononane Nonadiene 10 Decane Decene Decyne Cyclodecane Decadiene Usage Oil refineries are one way hydrocarbons are processed for use. Crude oil is processed in several stages to form desired hydrocarbons, used as fuel and in other products. Hydrocarbons are a primary energy source for current civilizations. The predominant use of hydrocarbons is as a combustible fuel source. In their solid form, hydrocarbons take the form of asphalt ( bitumen ). Mixtures of volatile hydrocarbons are now used in preference to the chlorofluorocarbons as a propellant for aerosol sprays, due to chlorofluorocarbons ' impact on the ozone layer. Methane ( CH ) and ethane ( C H ) are gaseous at ambient temperatures and can not be readily liquefied by pressure alone. Propane ( C H ) is however easily liquefied, and exists in ' propane bottles ' mostly as a liquid. Butane ( C H ) is so easily liquefied that it provides a safe, volatile fuel for small pocket lighters. Pentane ( C H ) is a clear liquid at room temperature, commonly used in chemistry and industry as a powerful nearly odorless solvent of waxes and high molecular weight organic compounds, including greases. Hexane ( C H ) is also a widely used non-polar, non-aromatic solvent, as well as a significant fraction of common gasoline. The C through C alkanes, alkenes and isomeric cycloalkanes are the top components of gasoline, naphtha, jet fuel and specialized industrial solvent mixtures. With the progressive addition of carbon units, the simple non-ring structured hydrocarbons have higher viscosities, lubricating indices, boiling points, solidification temperatures, and deeper color. At the opposite extreme from methane lie the heavy tars that remain as the lowest fraction in a crude oil refining retort. They are collected and widely utilized as roofing compounds, pavement composition, wood preservatives ( the creosote series ) and as extremely high viscosity shear - resisting liquids. Hydrocarbon use is also prevalent in nature. Some eusocial arthropods, such as the Brazilian stingless bee Schwarziana quadripunctata, use unique hydrocarbon `` scents '' in order to determine kin from non-kin. The chemical hydrocarbon composition varies between age, sex, nest location, and hierarchal position. Poisoning Hydrocarbon poisoning such as that of benzene and petroleum usually occurs accidentally by inhalation or ingestion of these cytotoxic chemical compounds. Intravenous or subcutaneous injection of petroleum compounds with intent of suicide or abuse is an extraordinary event that can result in local damage or systemic toxicity such as tissue necrosis, abscess formation, respiratory system failure and partial damage to the kidneys, the brain and the nervous system. Moaddab and Eskandarlou report a case of chest wall necrosis and empyema resulting from attempting suicide by injection of petroleum into the pleural cavity. Reactions There are three main types of reactions : Substitution reaction Addition reaction Combustion Substitution reactions Substitution reactions only occur in saturated hydrocarbons ( single carbon -- carbon bonds ). In this reaction, an alkane reacts with a chlorine molecule. One of the chlorine atoms displaces a hydrogen atom. This forms hydrochloric acid as well as the hydrocarbon with one chlorine atom. CH + Cl → CH Cl + HCl CH Cl + Cl → CH Cl + HCl all the way to CCl ( carbon tetrachloride ) C H + Cl → C H Cl + HCl C H Cl + Cl → C H Cl + HCl all the way to C Cl ( hexachloroethane ) Addition reactions Addition reactions involve alkenes and alkynes. In this reaction a halogen molecule breaks the double or triple bond in the hydrocarbon and forms a bond. Combustion Main article : Combustion Hydrocarbons are currently the main source of the world 's electric energy and heat sources ( such as home heating ) because of the energy produced when burnt. Often this energy is used directly as heat such as in home heaters, which use either petroleum or natural gas. The hydrocarbon is burnt and the heat is used to heat water, which is then circulated. A similar principle is used to create electric energy in power plants. Common properties of hydrocarbons are the facts that they produce steam, carbon dioxide and heat during combustion and that oxygen is required for combustion to take place. The simplest hydrocarbon, methane, burns as follows : CH + 2 O → 2 H O + CO + energy In inadequate supply of air, carbon monoxide gas and water vapour are formed : 2 CH + 3 O → 2 CO + 4 H O Another example of this reaction is propane : C H + 5 O → 4 H O + 3 CO + energy C H + 3n + 1 / 2 O → ( n + 1 ) H O + n CO + energy Burning of hydrocarbons is an example of an exothermic chemical reaction. Hydrocarbons can also be burned with elemental fluorine, resulting in carbon tetrafluoride and hydrogen fluoride products. Petroleum Main article : Petroleum Natural oil spring in Korňa, Slovakia. Extracted hydrocarbons in a liquid form are referred to as petroleum ( literally `` rock oil '' ) or mineral oil, whereas hydrocarbons in a gaseous form are referred to as natural gas. Petroleum and natural gas are found in the Earth 's subsurface with the tools of petroleum geology and are a significant source of fuel and raw materials for the production of organic chemicals. The extraction of liquid hydrocarbon fuel from sedimentary basins is integral to modern energy development. Hydrocarbons are mined from oil sands and oil shale, and potentially extracted from sedimentary methane hydrates. These reserves require distillation and upgrading to produce synthetic crude and petroleum. Oil reserves in sedimentary rocks are the source of hydrocarbons for the energy, transport and petrochemical industries. Economically important hydrocarbons include fossil fuels such as coal, petroleum and natural gas, and its derivatives such as plastics, paraffin, waxes, solvents and oils. Hydrocarbons -- along with NO and sunlight -- contribute to the formation of tropospheric ozone and greenhouse gases. Bioremediation Bacteria in the gabbroic layer of the ocean 's crust can degrade hydrocarbons ; but the extreme environment makes research difficult. Other bacteria such as Lutibacterium anuloederans can also degrade hydrocarbons. Mycoremediation or breaking down of hydrocarbon by mycellium and mushroom is possible. Safety Many hydrocarbons are highly flammable, therefore, care should be taken to prevent injury. Benzene and many aromatic compounds are possible carcinogens, and proper safety equipment must be worn to prevent these harmful compounds from entering the body. If hydrocarbons undergo combustion in tight areas, toxic carbon monoxide can form. Hydrocarbons should be kept away from fluorine compounds due to the high probability of forming toxic hydrofluoric acid. Environmental impact Hydrocarbons are introduced into the environment through their extensive use as fuels and chemicals as well as through leaks or accidental spills during exploration, production, refining, or transport. Anthropogenic hydrocarbon contamination of soil is a serious global issue due to contaminant persistence and the negative impact on human health. See also Abiogenic petroleum origin Biohydrocarbon Carbohydrate Energy storage Fractional distillation Functional group Hydrocarbon mixtures Organically moderated and cooled reactor References Jump up ^ Silberberg, 620 Jump up ^ IUPAC Goldbook hydrocarbyl groups Archived 7 January 2010 at the Wayback Machine. Jump up ^ Clayden, J., Greeves, N., et al. ( 2001 ) Organic Chemistry Oxford ISBN 0 - 19 - 850346 - 6 p. 21 Jump up ^ McMurry, J. ( 2000 ). Organic Chemistry 5th ed. Brooks / Cole : Thomson Learning. ISBN 0 - 495 - 11837 - 0 pp. 75 -- 81 Jump up ^ Silderberg, 623 Jump up ^ Silderberg, 625 Jump up ^ Silderberg, 627 Jump up ^ Meierhenrich, Uwe. Amino Acids and the Asymmetry of Life Archived 2 March 2017 at the Wayback Machine... Springer, 2008. ISBN 978 - 3 - 540 - 76885 - 2 Jump up ^ Silderberg, 628 Jump up ^ Silderberg, 631 Jump up ^ NASA 's Cassini Spacecraft Reveals Clues About Saturn Moon Archived 2 September 2014 at the Wayback Machine... NASA ( December 12, 2013 ) Jump up ^ Guzman - Ramirez, L. ; Lagadec, E. ; Jones, D. ; Zijlstra, A.A. ; Gesicki, K. ( 2014 ). `` PAH formation in O - rich planetary nebulae ''. Monthly Notices of the Royal Astronomical Society. 441 : 364. arXiv : 1403.1856. Bibcode : 2014MNRAS. 441... 364G. doi : 10.1093 / mnras / stu454. Jump up ^ Nunes, T.M. ; Turatti, I.C.C. ; Mateus, S. ; Nascimento, F.S. ; Lopes, N.P. ; Zucchi, R. ( 2009 ). `` Cuticular Hydrocarbons in the Stingless Bee Schwarziana quadripunctata ( Hymenoptera, Apidae, Meliponini ) : Differences between Colonies, Castes and Age '' ( PDF ). Genetics and Molecular Research. 8 ( 2 ) : 589 -- 595. doi : 10.4238 / vol8 - 2kerr012. PMID 19551647. Archived ( PDF ) from the original on 26 September 2015. Jump up ^ Eskandarlou, M ; Moaddab, AH ( Aug 2010 ). `` Chest wall necrosis and empyema resulting from attempting suicide by injection of petroleum into the pleural cavity ''. Emerg Med J. 27 ( 8 ) : 616 -- 8. doi : 10.1136 / emj. 2009.073486. PMID 20558490. Jump up ^ World Coal, Coal and Electricity Archived 22 October 2015 at the Wayback Machine... World Coal Association Jump up ^ Mason OU, Nakagawa T, Rosner M, Van Nostrand JD, Zhou J, Maruyama A, Fisk MR, Giovannoni SJ ( 2010 ). `` First investigation of the microbiology of the deepest layer of ocean crust ''. PLoS ONE. 5 ( 11 ) : e15399. Bibcode : 2010PLoSO... 515399M. doi : 10.1371 / journal. pone. 0015399. PMC 2974637. PMID 21079766. Jump up ^ Yakimov, M.M. ; Timmis, K.N. ; Golyshin, P.N. ( 2007 ). `` Obligate oil - degrading marine bacteria ''. Curr. Opin. Biotechnol. 18 ( 3 ) : 257 -- 266. CiteSeerX 10.1. 1.475. 3300. doi : 10.1016 / j. copbio. 2007.04. 006. PMID 17493798. Jump up ^ Stamets, Paul ( 2005 ) `` Mycoremediation Archived 31 October 2014 at the Wayback Machine. '', Ch. 7, p. 86, in Mycelium Running : How Mushrooms Can Help Save the World. ISBN 9781580085793 Jump up ^ `` Microbial Degradation of Alkanes ( PDF Download Available ) ''. ResearchGate. Archived from the original on 24 February 2017. Retrieved 23 February 2017. Bibliography Silberberg, Martin. Chemistry : The Molecular Nature Of Matter and Change. New York : McGraw - Hill Companies, 2004. ISBN 0 - 07 - 310169 - 9 External links Find more aboutHydrocarbonat Wikipedia 's sister projects Definitions from Wiktionary Media from Commons Quotations from Wikiquote Textbooks from Wikibooks Data from Wikidata The Methane Molecule Hydrocarbons Saturated aliphatic hydrocarbons Alkanes Linear alkanes Methane Ethane Propane Butane Pentane Hexane Heptane Octane Nonane Decane Branched alkanes Isobutane Isopentane 3 - Methylpentane Neopentane Isohexane Isoheptane Isooctane Isononane Isodecane Cycloalkanes Cyclopropane Cyclobutane Cyclopentane Cyclohexane Cycloheptane Cyclooctane Cyclononane Cyclodecane Alkylcycloalkanes Methylcyclopropane Methylcyclobutane Methylcyclopentane Methylcyclohexane Isopropylcyclohexane Bicycloalkanes Housane ( bicyclo ( 2.1. 0 ) pentane ) Norbornane ( bicyclo ( 2.2. 1 ) heptane ) Decalin ( bicyclo ( 4.4. 0 ) decane ) Polycycloalkanes Adamantane Diamondoid Perhydrophenanthrene Sterane Cubane Prismane Dodecahedrane Basketane Churchane Pagodane Twistane Other Spiroalkanes Unsaturated aliphatic hydrocarbons Alkenes Linear alkenes Ethene Propene Butene Pentene Hexene Heptene Octene Nonene Decene Branched alkenes Isobutene Isopentene Neopentene Isohexene Isoheptene Isooctene Isononene Isodecene Alkynes Linear alkynes Ethyne Propyne Butyne Pentyne Hexyne Heptyne Octyne Nonyne Decyne Branched alkynes Isobutyne Isopentyne Neopentyne Isohexyne Isoheptyne Isooctyne Isononyne Isodecyne Cycloalkenes Cyclopropene Cyclobutene Cyclopentene Cyclohexene Cycloheptene Cyclooctene Cyclononene Cyclodecene Alkyilcycloalkenes Methylcyclopropene Methylcyclobutene Methylcyclopentene Methylcyclohexene Isopropylcyclohexene Bicycloalkenes Norbornene Cycloalkynes Cyclopropyne Cyclobutyne Cyclopentyne Cyclohexyne Cycloheptyne Cycloctyne Cyclononyne Cyclodecyne Alkadienes Propadiene Butadiene Pentadiene Hexadiene Heptadiene Octadiene Nonadiene Decadiene Other Alkatriene Alkadiyne Alkenyne Cumulene Cyclooctatetraene Cyclododecatriene Aromatic hydrocarbons PAHs Acenes Naphthalene Anthracene Naphthacene Pentacene Hexacene Other Azulene Fluorene Helicenes Circulenes Alkylbenzenes Toluene Xylene Ethylbenzene Cumene Styrene Mesitylene Pseudocumene Hexamethylbenzene Other Benzene Phenanthrene Chrysene Pyrene Corannulene Kekulene Other Annulenes Annulynes Alicyclic compounds LCCN : sh85063372 GND : 4125165 - 9 NDL : 00572658 NKC : ph116523 Retrieved from `` https://en.wikipedia.org/w/index.php?title=Hydrocarbon&oldid=812077331 '' Categories : Hydrocarbons Hidden categories : Webarchive template wayback links Wikipedia articles with LCCN identifiers Wikipedia articles with GND identifiers Use dmy dates from September 2010 Talk Contents About Wikipedia Wikiquote Afrikaans አማርኛ Azərbaycanca বাংলা Беларуская Беларуская ( тарашкевіца ) ‎ Български Boarisch Bosanski Brezhoneg Català Čeština Cymraeg Dansk Deutsch Eesti Ελληνικά Español Esperanto Euskara فارسی Français Gaeilge Galego ગુજરાતી 客家 語 / Hak - kâ - ngî 한국어 Հայերեն हिन्दी Hrvatski Ido Bahasa Indonesia Íslenska Italiano עברית Basa Jawa ಕನ್ನಡ ქართული Қазақша Kiswahili Kreyòl ayisyen Latina Latviešu Lëtzebuergesch Lietuvių Magyar Македонски മലയാളം मराठी Bahasa Melayu Монгол Nederlands नेपाली 日本 語 Nordfriisk Norsk Norsk nynorsk Occitan Oʻzbekcha / ўзбекча ਪੰਜਾਬੀ پنجابی Polski Português Română Русский Scots Shqip Sicilianu සිංහල Simple English Slovenčina Slovenščina کوردی Српски / srpski Srpskohrvatski / српскохрватски Basa Sunda Suomi Svenska Tagalog தமிழ் Татарча / tatarça ไทย Türkçe Українська اردو Tiếng Việt Winaray 粵語 中文 Edit links This page was last edited on 25 November 2017, at 21 : 35. 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Question: a hydrocarbon with a double bond is an
Answer: alkenes