{"id":2335,"date":"2018-06-19T20:26:35","date_gmt":"2018-06-19T20:26:35","guid":{"rendered":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry\/chapter\/3-4-naming-alkanes\/"},"modified":"2018-08-06T06:39:36","modified_gmt":"2018-08-06T06:39:36","slug":"3-1-nomenclature-of-alkanes-related-structures","status":"publish","type":"chapter","link":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry\/chapter\/3-1-nomenclature-of-alkanes-related-structures\/","title":{"raw":"3.1. Nomenclature of alkanes &amp; related structures","rendered":"3.1. Nomenclature of alkanes &amp; related structures"},"content":{"raw":"<section class=\"mt-content-container\">\r\n<div class=\"textbox learning-objectives\">\r\n<h3 class=\"boxtitle\">Learning Objectives<\/h3>\r\nAfter completing this section, you should be able to\r\n<ol>\r\n \t<li>provide the correct IUPAC name for any given alkane structure (Kekul\u00e9, condensed or shorthand).<\/li>\r\n \t<li>draw the Kekul\u00e9, condensed or shorthand structure of an alkane, given its IUPAC name.<\/li>\r\n<\/ol>\r\n<\/div>\r\n<div>\r\n<div class=\"textbox key-takeaways\">\r\n<h3>Key Terms<\/h3>\r\nMake certain that you can define, and use in context, the key term below.\r\n<ul>\r\n \t<li>IUPAC system<\/li>\r\n<\/ul>\r\n<\/div>\r\n<\/div>\r\n<div class=\"textbox key-takeaways\">\r\n<h3 class=\"boxtitle\">Study Notes<\/h3>\r\nThe IUPAC system of nomenclature aims to ensure\r\n<ol>\r\n \t<li>that every organic compound has a unique, unambiguous name.<\/li>\r\n \t<li>that the IUPAC name of any compound conveys the structure of that compound to a person familiar with the system.<\/li>\r\n<\/ol>\r\nOne way of checking whether the name you have given to an alkane is reasonable is to count the number of carbon atoms implied by the chosen name. For example, if you named a compound 3\u2011ethyl-4\u2011methylheptane, you have indicated that the compound contains a total of 10 carbon atoms\u2014seven carbon atoms in the main chain, two carbon atoms in an ethyl group, and one carbon atom in a methyl group. If you were to check the given structure and find 11 carbon atoms, you would know that you had made a mistake. Perhaps the name you should have written was 3\u2011ethyl-4,4\u2011dimethylheptane!\r\n\r\nWhen naming alkanes, a common error of beginning students is a failure to pick out the longest carbon chain. For example, the correct name for the compound shown below is 3\u2011methylheptane, not 2\u2011ethylhexane.\r\n<p class=\"max-66\"><img class=\"aligncenter\" src=\"http:\/\/chem.libretexts.org\/@api\/deki\/files\/85405\/3-4.png?origin=mt-web\" alt=\"3-methylheptane\" \/><\/p>\r\nRemember that every substituent must have a number, and do not forget the prefixes: di, tri, tetra, etc.\r\n\r\nYou must use commas to separate numbers, and hyphens to separate numbers and substituents. Notice that 3\u2011methylhexane is one word.\r\n\r\n<\/div>\r\n<h3 class=\"title editable block\">Hydrocarbons<\/h3>\r\nThe simplest class of organic compounds is the <span class=\"margin_term\"><a class=\"glossterm\">hydrocarbons<\/a><\/span>, which consist entirely of carbon and hydrogen. Petroleum and natural gas are complex, naturally occurring mixtures of many different hydrocarbons that furnish raw materials for the chemical industry. The four major classes of hydrocarbons are the following: the <span class=\"margin_term\"><a class=\"glossterm\">alkanes<\/a><\/span>, which contain only carbon\u2013hydrogen and carbon\u2013carbon single bonds; the <span class=\"margin_term\"><a class=\"glossterm\">alkenes<\/a><\/span>, which contain at least one carbon\u2013carbon double bond; the <span class=\"margin_term\"><a class=\"glossterm\">alkynes<\/a><\/span>, which contain at least one carbon\u2013carbon triple bond; and the <span class=\"margin_term\"><a class=\"glossterm\">aromatic hydrocarbons<\/a><\/span>, which usually contain rings of six carbon atoms that can be drawn with alternating single and double bonds. Alkanes are also called <em class=\"emphasis\">saturated<\/em> hydrocarbons, whereas hydrocarbons that contain multiple bonds (alkenes, alkynes, and aromatics) are <em class=\"emphasis\">unsaturated<\/em>.\r\n<h2>Alkanes<\/h2>\r\n[embed]https:\/\/vimeo.com\/181357040[\/embed]\r\n\r\n<img class=\"size-thumbnail wp-image-4067 alignnone\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/26155057\/frame-11-150x150.png\" alt=\"\" width=\"150\" height=\"150\" \/>\r\n\r\nHydrocarbons having no double or triple bond functional groups are classified as <strong>alkanes<\/strong> or <strong>cycloalkanes<\/strong>, depending on whether the carbon atoms of the molecule are arranged only in chains or also in rings. Although these hydrocarbons have no functional groups, they constitute the framework on which functional groups are located in other classes of compounds, and provide an ideal starting point for studying and naming organic compounds. The alkanes and cycloalkanes are also members of a larger class of compounds referred to as <strong>aliphatic<\/strong>. Simply put, aliphatic compounds are compounds that do not incorporate any aromatic rings in their molecular structure.\r\n\r\nThe following table lists the IUPAC names assigned to simple continuous-chain alkanes from C-1 to C-10. A common <strong>\"ane\"<\/strong> suffix identifies these compounds as alkanes. Longer chain alkanes are well known, and their names may be found in many reference and text books. The names <strong>methane<\/strong> through <strong>decane<\/strong> should be memorized, since they constitute the root of many IUPAC names. Fortunately, common numerical prefixes are used in naming chains of five or more carbon atoms.\r\n<table style=\"width: 678px\" border=\"1\" cellpadding=\"4\"><caption><em><strong>Table 1<\/strong>: Simple Unbranched Alkanes<\/em><\/caption>\r\n<thead>\r\n<tr style=\"background-color: #ccffcc\" align=\"center\">\r\n<th style=\"width: 68px\" scope=\"col\"><strong>Name<\/strong><\/th>\r\n<th style=\"width: 89px\" scope=\"col\"><strong>Molecular\r\nFormula<\/strong><\/th>\r\n<th style=\"width: 116px\" scope=\"col\"><strong>Structural\r\nFormula<\/strong><\/th>\r\n<th style=\"width: 74px\" scope=\"col\"><strong>Isomers<\/strong><\/th>\r\n<th style=\"width: 11px\" scope=\"col\"><\/th>\r\n<th style=\"width: 64px\" scope=\"col\"><strong>Name<\/strong><\/th>\r\n<th style=\"width: 89px\" scope=\"col\"><strong>Molecular\r\nFormula<\/strong><\/th>\r\n<th style=\"width: 90px\" scope=\"col\"><strong>Structural\r\nFormula<\/strong><\/th>\r\n<th style=\"width: 74px\" scope=\"col\"><strong>Isomers<\/strong><\/th>\r\n<\/tr>\r\n<\/thead>\r\n<tbody>\r\n<tr align=\"center\">\r\n<td style=\"width: 68px\">meth<strong>ane<\/strong><\/td>\r\n<td style=\"width: 89px\">CH<sub>4<\/sub><\/td>\r\n<td style=\"width: 116px\">CH<sub>4<\/sub><\/td>\r\n<td style=\"width: 74px\">1<\/td>\r\n<td style=\"width: 11px\"><\/td>\r\n<td style=\"width: 64px\">hex<strong>ane<\/strong><\/td>\r\n<td style=\"width: 89px\">C<sub>6<\/sub>H<sub>14<\/sub><\/td>\r\n<td style=\"width: 90px\">CH<sub>3<\/sub>(CH<sub>2<\/sub>)<sub>4<\/sub>CH<sub>3<\/sub><\/td>\r\n<td style=\"width: 74px\">5<\/td>\r\n<\/tr>\r\n<tr align=\"center\">\r\n<td style=\"width: 68px\">eth<strong>ane<\/strong><\/td>\r\n<td style=\"width: 89px\">C<sub>2<\/sub>H<sub>6<\/sub><\/td>\r\n<td style=\"width: 116px\">CH<sub>3<\/sub>CH<sub>3<\/sub><\/td>\r\n<td style=\"width: 74px\">1<\/td>\r\n<td style=\"width: 11px\"><\/td>\r\n<td style=\"width: 64px\">hept<strong>ane<\/strong><\/td>\r\n<td style=\"width: 89px\">C<sub>7<\/sub>H<sub>16<\/sub><\/td>\r\n<td style=\"width: 90px\">CH<sub>3<\/sub>(CH<sub>2<\/sub>)<sub>5<\/sub>CH<sub>3<\/sub><\/td>\r\n<td style=\"width: 74px\">9<\/td>\r\n<\/tr>\r\n<tr align=\"center\">\r\n<td style=\"width: 68px\">prop<strong>ane<\/strong><\/td>\r\n<td style=\"width: 89px\">C<sub>3<\/sub>H<sub>8<\/sub><\/td>\r\n<td style=\"width: 116px\">CH<sub>3<\/sub>CH<sub>2<\/sub>CH<sub>3<\/sub><\/td>\r\n<td style=\"width: 74px\">1<\/td>\r\n<td style=\"width: 11px\"><\/td>\r\n<td style=\"width: 64px\">oct<strong>ane<\/strong><\/td>\r\n<td style=\"width: 89px\">C<sub>8<\/sub>H<sub>18<\/sub><\/td>\r\n<td style=\"width: 90px\">CH<sub>3<\/sub>(CH<sub>2<\/sub>)<sub>6<\/sub>CH<sub>3<\/sub><\/td>\r\n<td style=\"width: 74px\">18<\/td>\r\n<\/tr>\r\n<tr align=\"center\">\r\n<td style=\"width: 68px\">but<strong>ane<\/strong><\/td>\r\n<td style=\"width: 89px\">C<sub>4<\/sub>H<sub>10<\/sub><\/td>\r\n<td style=\"width: 116px\">CH<sub>3<\/sub>CH<sub>2<\/sub>CH<sub>2<\/sub>CH<sub>3<\/sub><\/td>\r\n<td style=\"width: 74px\">2<\/td>\r\n<td style=\"width: 11px\"><\/td>\r\n<td style=\"width: 64px\">non<strong>ane<\/strong><\/td>\r\n<td style=\"width: 89px\">C<sub>9<\/sub>H<sub>20<\/sub><\/td>\r\n<td style=\"width: 90px\">CH<sub>3<\/sub>(CH<sub>2<\/sub>)<sub>7<\/sub>CH<sub>3<\/sub><\/td>\r\n<td style=\"width: 74px\">35<\/td>\r\n<\/tr>\r\n<tr align=\"center\">\r\n<td style=\"width: 68px\">pent<strong>ane<\/strong><\/td>\r\n<td style=\"width: 89px\">C<sub>5<\/sub>H<sub>12<\/sub><\/td>\r\n<td style=\"width: 116px\">CH<sub>3<\/sub>(CH<sub>2<\/sub>)<sub>3<\/sub>CH<sub>3<\/sub><\/td>\r\n<td style=\"width: 74px\">3<\/td>\r\n<td style=\"width: 11px\"><\/td>\r\n<td style=\"width: 64px\">dec<strong>ane<\/strong><\/td>\r\n<td style=\"width: 89px\">C<sub>10<\/sub>H<sub>22<\/sub><\/td>\r\n<td style=\"width: 90px\">CH<sub>3<\/sub>(CH<sub>2<\/sub>)<sub>8<\/sub>CH<sub>3<\/sub><\/td>\r\n<td style=\"width: 74px\">75<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<div>\r\n<div class=\"textbox key-takeaways\">\r\n<div>\r\n<h3 class=\"boxtitle\">Some important behavior trends and terminologies<\/h3>\r\n<ol>\r\n \t<li>The formulas and structures of these alkanes increase uniformly by a CH<sub>2<\/sub> increment.<\/li>\r\n \t<li>A uniform variation of this kind in a series of compounds is called <strong>homologous<\/strong>.<\/li>\r\n \t<li>These formulas all fit the <strong>C<sub>n<\/sub>H<sub>2n<\/sub><sub>+2<\/sub><\/strong> rule (for acyclic aka non-cyclic) alkanes. This is also the highest possible H\/C ratio for a stable hydrocarbon.<\/li>\r\n \t<li>Since the H\/C ratio in these compounds is at a maximum, we call them <strong>saturated<\/strong> (with hydrogen).<\/li>\r\n<\/ol>\r\n<\/div>\r\n<\/div>\r\n<section class=\"mt-content-container\">\r\n<div class=\"mt-section\">\r\n<div id=\"averill_1.0-ch02_s04_s02_s04\" class=\"section\">\r\n<div class=\"mt-section\">\r\n<h3 class=\"title editable block\">Cyclic hydrocarbons<\/h3>\r\n<p id=\"averill_1.0-ch02_s04_s02_s04_p01\" class=\"para editable block\">In a cyclic hydrocarbon, the ends of a hydrocarbon chain are connected to form a ring of covalently bonded carbon atoms. Cyclic hydrocarbons are named by attaching the prefix <em class=\"emphasis\">cyclo<\/em>- to the name of the alkane, the alkene, or the alkyne. The simplest cyclic alkanes are <em class=\"emphasis\">cyclopropane<\/em> (C<sub class=\"subscript\">3<\/sub>H<sub class=\"subscript\">6<\/sub>) a flammable gas that is also a powerful anesthetic, and <em class=\"emphasis\">cyclobutane<\/em> (C<sub class=\"subscript\">4<\/sub>H<sub class=\"subscript\">8<\/sub>) (part (c) in <span class=\"xref external\">Figure 3.7.2<\/span>). The most common way to draw the structures of cyclic alkanes is to sketch a polygon with the same number of vertices as there are carbon atoms in the ring; each vertex represents a CH<sub class=\"subscript\">2<\/sub> unit. The structures of the cycloalkanes that contain three to six carbon atoms are shown schematically in <span class=\"xref external\">the figure below:\r\n<\/span><\/p>\r\n\r\n<div id=\"averill_1.0-ch02_s04_s02_s04_f01\" class=\"figure large medium-height editable block\">\r\n\r\n[caption id=\"\" align=\"aligncenter\" width=\"494\"]<img class=\"internal\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202703\/90bd930211dd9973f28d67347758d8ce.jpg\" alt=\"\" width=\"494\" height=\"364\" \/> <em>The simple cycloalkanes<\/em>[\/caption]\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<h3 class=\"editable\">Alkyl groups<a class=\"mt-disabled\" title=\"Edit section\" rel=\"broken\"><span class=\"icon\"><img class=\"sectionedit\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202603\/icon-trans.gif\" alt=\"Edit section\" \/><\/span><\/a><\/h3>\r\n<p class=\"paragraph\">Acyclic <a class=\"internal\" title=\"Organic Chemistry\/Hydrocarbons\/Alkanes\" href=\"\/Organic_Chemistry\/Hydrocarbons\/Alkanes\" rel=\"internal\">alkanes <\/a>can be described by the general formula C<sub class=\"subscript\">n<\/sub>H<sub class=\"subscript\">2n<\/sub><sub class=\"subscript\">+2<\/sub>. An alkyl group is formed by removing one hydrogen from the alkane chain and is described by the formula C<sub class=\"subscript\">n<\/sub>H<sub class=\"subscript\">2n<\/sub><sub class=\"subscript\">+1<\/sub>. The removal of this hydrogen results in a stem change from <strong class=\"bold\">-ane<\/strong> to <strong class=\"bold\">-yl<\/strong>. Take a look at the following examples.<img class=\"alignnone wp-image-4750\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/06062115\/Alkyls.png\" alt=\"\" width=\"388\" height=\"152\" \/><\/p>\r\n\r\n<\/div>\r\n<\/section><section class=\"mt-content-container\">\r\n<div class=\"mt-section\">\r\n<p class=\"paragraph\">The same concept can be applied to any of the straight chain alkane names provided in the table above.\u00a0 Examples of some common <strong>alkyl groups<\/strong> are given in the following table. Note that the \"ane\" suffix is replaced by \"<strong>yl<\/strong>\" in naming groups. The symbol <strong>R<\/strong> is used to designate a generic (unspecified) alkyl group.<\/p>\r\n\r\n<table cellpadding=\"5\"><caption><em><strong>Table 2<\/strong>: Alkyl Groups Names<\/em><\/caption>\r\n<tbody>\r\n<tr align=\"center\" valign=\"middle\">\r\n<th scope=\"row\">Group<\/th>\r\n<td>CH<sub>3<\/sub>\u2013<\/td>\r\n<td>C<sub>2<\/sub>H<sub>5<\/sub>\u2013<\/td>\r\n<td>CH<sub>3<\/sub>CH<sub>2<\/sub>CH<sub>2<\/sub>\u2013<\/td>\r\n<td>(CH<sub>3<\/sub>)<sub>2<\/sub>CH\u2013<\/td>\r\n<td>CH<sub>3<\/sub>CH<sub>2<\/sub>CH<sub>2<\/sub>CH<sub>2<\/sub>\u2013<\/td>\r\n<td>(CH<sub>3<\/sub>)<sub>2<\/sub>CHCH<sub>2<\/sub>\u2013<\/td>\r\n<td>CH<sub>3<\/sub>CH<sub>2<\/sub>CH(CH<sub>3<\/sub>)\u2013<\/td>\r\n<td>(CH<sub>3<\/sub>)<sub>3<\/sub>C\u2013<\/td>\r\n<td>R\u2013<\/td>\r\n<\/tr>\r\n<tr align=\"center\" valign=\"middle\">\r\n<th scope=\"row\">Name<\/th>\r\n<td>Methyl<\/td>\r\n<td>Ethyl<\/td>\r\n<td>Propyl<\/td>\r\n<td>Isopropyl<\/td>\r\n<td>Butyl<\/td>\r\n<td>Isobutyl<\/td>\r\n<td>sec-Butyl<\/td>\r\n<td>tert-Butyl<\/td>\r\n<td>\u00a0 Alkyl<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\nSimilarly, groups of atoms derived from aromatic hydrocarbons are <em class=\"emphasis\">aryl groups<\/em>, which sometimes have unexpected names. For example, the \u2013C<sub class=\"subscript\">6<\/sub>H<sub class=\"subscript\">5<\/sub> fragment is derived from benzene, but it is called a <em class=\"emphasis\">phenyl<\/em> group. In general formulas and structures, alkyl and aryl groups are often abbreviated as <span class=\"margin_term\"><a class=\"glossterm\">R<\/a><\/span>.<a title=\"90d23185727828608152de77268572b8.jpg\" href=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/30410\/90d23185727828608152de77268572b8.jpg?revision=3\" rel=\"internal\"><img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202726\/90d23185727828608152de77268572b8.jpg\" alt=\"\" width=\"237\" height=\"196\" \/><\/a>\r\n<h3>Naming complex alkanes<\/h3>\r\n[embed]https:\/\/vimeo.com\/183372579[\/embed]\r\n\r\n<img class=\"size-thumbnail wp-image-4068 alignnone\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/26155149\/frame-12-150x150.png\" alt=\"\" width=\"150\" height=\"150\" \/>\r\n\r\nBeginning with butane (C<sub>4<\/sub>H<sub>10<\/sub>), and becoming more numerous with larger alkanes, we note the existence of alkane isomers. For example, there are five C<sub>6<\/sub>H<sub>14<\/sub> isomers, shown below as abbreviated line formulas (<strong>A<\/strong> through E):\r\n\r\n<\/div>\r\n<\/section><\/div>\r\n<p style=\"text-align: center\"><img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202602\/c6h14.gif\" alt=\"c6h14.gif\" \/><\/p>\r\nAlthough these distinct compounds all have the same molecular formula, only one (<strong>A<\/strong>) can be called hexane. How then are we to name the others?\u00a0 (Answers below.)\r\n\r\nThe <strong>IUPAC<\/strong> system requires first that we have names for simple unbranched chains, as noted above, and second that we have names for simple alkyl groups that may be attached to the chains. Examples of some common <strong>alkyl groups<\/strong> are given in the following table. Note that the \"ane\" suffix is replaced by \"<strong>yl<\/strong>\" in naming groups. The symbol <strong>R<\/strong> is used to designate a generic (unspecified) alkyl group.\r\n<div class=\"mt-section\">\r\n<h4 class=\"editable\">IUPAC Rules for Alkane Nomenclature<\/h4>\r\n<\/div>\r\n<ol>\r\n \t<li>\u00a0Find and name the longest continuous carbon chain.<\/li>\r\n \t<li>\u00a0Identify and name groups attached to this chain.<\/li>\r\n \t<li>\u00a0Number the chain consecutively, starting at the end nearest a substituent group.<\/li>\r\n \t<li>\u00a0Designate the location of each substituent group by an appropriate number and name.<\/li>\r\n \t<li>\u00a0Assemble the name, listing groups in alphabetical order.<\/li>\r\n \t<li>\u00a0The prefixes di, tri, tetra etc., used to designate several groups of the same kind, are not considered when alphabetizing.<\/li>\r\n<\/ol>\r\nFor the above isomers of hexane the IUPAC names are: \u00a0 B\u00a0 2-methylpentane\u00a0\u00a0\u00a0 C\u00a0 3-methylpentane\u00a0\u00a0\u00a0 D\u00a0 2,2-dimethylbutane\u00a0\u00a0\u00a0 E\u00a0 2,3-dimethylbutane.\r\n<h2>Naming alkyl halides<\/h2>\r\n<strong>Halogen substituents<\/strong> are easily accommodated, using the names: fluoro (F-), chloro (Cl-), bromo (Br-) and iodo (I-).\u00a0 These are inserted alphabetically into the name in the same way as alkyl groups are included when naming complex alkanes.\r\n<div>\r\n<div class=\"textbox examples\">\r\n<h3 class=\"boxtitle\">Example: Halogen Substitution<\/h3>\r\nFor example, (CH<sub>3<\/sub>)<sub>2<\/sub>CHCH<sub>2<\/sub>CH<sub>2<\/sub>Br would be named 1-bromo-3-methylbutane. If the halogen is bonded to a simple alkyl group an alternative \"alkyl halide\" name may be used. Thus, C<sub>2<\/sub>H<sub>5<\/sub>Cl may be named chloroethane (no locator number is needed for a two carbon chain) or ethyl chloride.\r\n\r\n<\/div>\r\n<\/div>\r\n<\/section><section class=\"mt-content-container\">\r\n<div class=\"mt-section\">\r\n<div class=\"mt-page-section\">\r\n<div class=\"mt-section\">\r\n<div>\r\n<div class=\"textbox exercises\">\r\n<h3>Example<\/h3>\r\n<p class=\"paragraph\">What is the name of the following molecule?<\/p>\r\n<p class=\"paragraph\"><img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202608\/NamingAlkanes-Numbering_01.gif\" alt=\"NamingAlkanes-Numbering 01.gif\" width=\"257\" height=\"114\" \/><\/p>\r\n<p class=\"paragraph\">[reveal-answer q=\"317866\"]Show Solution[\/reveal-answer]\r\n[hidden-answer a=\"317866\"]<\/p>\r\n<p class=\"paragraph\"><strong class=\"bold\">Step #1:<\/strong> Choose the longest, most substituted carbon chain containing a functional group. This example does not contain any functional groups, so we only need to be concerned with choosing the longest, most substituted carbon chain. The longest carbon chain has been highlighted in red and consists of eight carbons.<\/p>\r\n<p class=\"paragraph\"><img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202610\/NamingAlkanes-Numbering_02.gif\" alt=\"NamingAlkanes-Numbering 02.gif\" width=\"301\" height=\"134\" \/><\/p>\r\n<p class=\"paragraph\"><strong class=\"bold\">Step #2:<\/strong> Carbons bonded to a functional group must have the lowest possible carbon number. If there are no functional groups, then any substituent present must have the lowest possible number.\u00a0Because this example does not contain any functional groups, we only need to be concerned with the two substituents present, that is, the two methyl groups. If we begin numbering the chain from the left, the methyls would be assigned the numbers 4 and 7, respectively. If we begin numbering the chain from the right, the methyls would be assigned the numbers 2 and 5. Therefore, to satisfy the second rule, numbering begins on the right side of the carbon chain as shown below. This gives the methyl groups the lowest possible numbering.<\/p>\r\n<p class=\"paragraph\"><img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202612\/NamingAlkanes-Numbering_03.gif\" alt=\"NamingAlkanes-Numbering 03.GIF\" width=\"311\" height=\"134\" \/><\/p>\r\n<p class=\"paragraph\"><strong>Alphebetization: <\/strong>In this example, there is no need to utilize the third rule.\u00a0Because the two substituents are identical, neither takes alphabetical precedence with respect to numbering the carbons. This concept will become clearer in the following examples.<\/p>\r\n<p class=\"paragraph\">The name of this molecule is thus: <strong>2,5-dimethyloctane<\/strong><\/p>\r\n[\/hidden-answer]\r\n\r\n<\/div>\r\n<\/div>\r\n<div>\r\n<div class=\"textbox exercises\">\r\n<h3>Example<\/h3>\r\n<p class=\"paragraph\">What is the name of the following molecule?<\/p>\r\n<p class=\"paragraph\"><img class=\"internal\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202614\/NamingAlkanes-Numbering_08DSL.gif\" alt=\"\" width=\"269\" height=\"119\" \/><\/p>\r\n<p class=\"paragraph\">[reveal-answer q=\"794732\"]Show Solution[\/reveal-answer]\r\n[hidden-answer a=\"794732\"]<\/p>\r\n<p class=\"paragraph\"><strong class=\"bold\">Step #1<\/strong>: Choose the longest, most substituted carbon chain containing a functional group. This example contains two functional groups, bromine and chlorine. The longest carbon chain has been highlighted in red and consists of seven carbons.<\/p>\r\n<p class=\"paragraph\"><img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202616\/NamingAlkanes-Numbering_05.gif\" alt=\"NamingAlkanes-Numbering 05.GIF\" width=\"269\" height=\"108\" \/><\/p>\r\n<p class=\"paragraph\"><strong class=\"bold\">Step #2:<\/strong> Carbons bonded to a functional group must have the lowest possible carbon number. If there are no functional groups, then any substituent present must have the lowest possible number. In this example, numbering the chain from the left or the right would satisfy this rule. If we number the chain from the left, bromine and chlorine would be assigned the second and sixth carbon positions, respectively. If we number the chain from the right, chlorine would be assigned the second position and bromine would be assigned the sixth position. In other words, whether we choose to number from the left or right, the functional groups occupy the second and sixth positions in the chain. To select the correct numbering scheme, we need to utilize the third rule.<\/p>\r\n<p class=\"paragraph\"><img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202618\/NamingAlkanes-Numbering_06.gif\" alt=\"NamingAlkanes-Numbering 06.GIF\" width=\"608\" height=\"108\" \/><\/p>\r\n<p class=\"paragraph\"><strong class=\"bold\">Alphabetizing:<\/strong> After applying the first two rules, take the alphabetical order into consideration. Alphabetically, bromine comes before chlorine. Therefore, bromine is assigned the second carbon position, and chlorine is assigned the sixth carbon position.<\/p>\r\n<p class=\"paragraph\"><img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202620\/NamingAlkanes-Numbering_07.gif\" alt=\"NamingAlkanes-Numbering 07.GIF\" width=\"269\" height=\"108\" \/><\/p>\r\n<p class=\"paragraph mt-align-left\">The name of this molecule is thus: <strong>2-bromo-6-chloroheptane<\/strong><\/p>\r\n[\/hidden-answer]\r\n\r\n<\/div>\r\n<\/div>\r\n<div>\r\n<div class=\"textbox exercises\">\r\n<h3>Example<\/h3>\r\n<p class=\"paragraph\">What is the name of the following molecule?<\/p>\r\n<p class=\"paragraph\"><img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202622\/NamingAlkanes-Numbering_08.gif\" alt=\"NamingAlkanes-Numbering 08.GIF\" width=\"269\" height=\"119\" \/><\/p>\r\n<p class=\"paragraph\">[reveal-answer q=\"597266\"]Show Solution[\/reveal-answer]\r\n[hidden-answer a=\"597266\"]<\/p>\r\n<p class=\"paragraph\"><strong class=\"bold\">Step #1<\/strong>: Choose the longest, most substituted carbon chain containing a functional group. This example contains two functional groups, bromine and chlorine, and one substitute, the methyl group. The longest carbon chain has been highlighted in red and consists of seven carbons.<\/p>\r\n<p class=\"paragraph\"><img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202624\/NamingAlkanes-Numbering_09.gif\" alt=\"NamingAlkanes-Numbering 09.GIF\" width=\"269\" height=\"119\" \/><\/p>\r\n<p class=\"paragraph\"><strong class=\"bold\">Step #2:<\/strong> Carbons bonded to a functional group must have the lowest possible carbon number. After taking functional groups into consideration, any substituents present must have the lowest possible carbon number. This particular example illustrates the <strong class=\"bold\">point of difference principle<\/strong>. If we number the chain from the left, bromine, the methyl group and chlorine would occupy the second, fifth and sixth positions, respectively. This concept is illustrated in the second drawing below. If we number the chain from the right, chlorine, the methyl group and bromine would occupy the second, third and sixth positions, respectively, which\u00a0is illustrated in the first drawing below. The position of the methyl, therefore, becomes a <strong class=\"bold\">point of difference<\/strong>. In the first drawing, the methyl\u00a0occupies the third position. In the second drawing, the methyl occupies the fifth position. To satisfy the second rule, we want to choose the numbering scheme that provides the lowest possible numbering of this substituent. Therefore, the first of the two carbon chains shown below is correct.<\/p>\r\n<p class=\"paragraph\"><img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202626\/NamingAlkanes-Numbering_10.gif\" alt=\"NamingAlkanes-Numbering 10.GIF\" width=\"269\" height=\"243\" \/><\/p>\r\n<p class=\"paragraph\">Therefore,\u00a0the first numbering scheme is the appropriate one to use.<\/p>\r\n<p class=\"paragraph\"><img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202627\/NamingAlkanes-Naming_01.gif\" alt=\"NamingAlkanes-Naming 01.GIF\" width=\"269\" height=\"108\" \/><\/p>\r\n<p class=\"paragraph\">Once you have determined the correct numbering of the carbons, it is often useful to make a list, including the functional groups, substitutes, and the name of the parent chain.<\/p>\r\n<p class=\"paragraph\"><strong class=\"bold\">Alphabetization:<\/strong> After applying the first two rules, take the alphabetical order into consideration. Alphabetically, bromine comes before chlorine. Therefore, bromine is assigned the second carbon position, and chlorine is assigned the sixth carbon position.<\/p>\r\n<p class=\"paragraph\">Parent chain: heptane 2-Chloro 3-Methyl 6-Bromo<\/p>\r\n<p class=\"paragraph\" style=\"text-align: center\">6-bromo-2-chloro-3-methylheptane<\/p>\r\n[\/hidden-answer]\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div class=\"mt-section\">\r\n<div class=\"textbox exercises\">\r\n<h3>Exercises<\/h3>\r\n<div id=\"s61690\" class=\"mt-include\">\r\n<div id=\"section_14\" class=\"mt-section\">\r\n<div id=\"section_15\" class=\"mt-section\">\r\n<h4 id=\"Questions-61690\">Question<\/h4>\r\n<span class=\"mt-font-Times New Roman,serif\"><span class=\"mt-font-size-12.0pt\">Give the name of the following molecules:<\/span><\/span>\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202633\/3.42.png\" alt=\"\" width=\"455\" height=\"279\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_16\" class=\"mt-section\">\r\n\r\n&nbsp;\r\n<p id=\"Solutions-61690\">[reveal-answer q=\"785873\"]Show Solutions[\/reveal-answer]\r\n[hidden-answer a=\"785873\"]<\/p>\r\n<span class=\"mt-font-Times New Roman,serif\"><span class=\"mt-font-size-12.0pt\">1 is 3,4-Dimethylhexane<\/span><\/span>\r\n\r\n<span class=\"mt-font-Times New Roman,serif\"><span class=\"mt-font-size-12.0pt\">2 is 2-methylpentane<\/span><\/span>\r\n\r\n<span class=\"mt-font-Times New Roman,serif\"><span class=\"mt-font-size-12.0pt\">3 is 2,2,4-trimethylpentane<\/span><\/span>\r\n\r\n[\/hidden-answer]\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div class=\"mt-section\">\r\n<h2>Naming ethers<\/h2>\r\n<section class=\"mt-content-container\">Ethers are compounds having two alkyl or aryl groups bonded to an oxygen atom, as in the formula R<sup>1<\/sup>\u2013O\u2013R<sup>2<\/sup>. The ether functional group does not have a characteristic IUPAC nomenclature suffix, so it is necessary to designate it as a substituent. To do so the common alkoxy substituents are given names derived from their alkyl component (below):<\/section><\/div>\r\n<\/div>\r\n<\/section>\r\n<table style=\"margin: auto\" border=\"1\" cellpadding=\"5\">\r\n<thead>\r\n<tr style=\"height: 15px\">\r\n<th style=\"background-color: #ddffdd;height: 15px\" scope=\"col\">Alkyl Group<\/th>\r\n<th style=\"background-color: #ddffdd;height: 15px\" scope=\"col\">Name<\/th>\r\n<th style=\"height: 15px\" scope=\"col\"><\/th>\r\n<th style=\"background-color: #ddddff;height: 15px\" scope=\"col\">Alkoxy Group<\/th>\r\n<th style=\"background-color: #ddddff;height: 15px\" scope=\"col\">Name<\/th>\r\n<\/tr>\r\n<\/thead>\r\n<tbody>\r\n<tr style=\"height: 18px\">\r\n<td style=\"height: 18px\">CH<sub>3<\/sub>\u2013<\/td>\r\n<td style=\"height: 18px\">Methyl<\/td>\r\n<td style=\"height: 18px\"><\/td>\r\n<td style=\"height: 18px\">CH<sub>3<\/sub>O\u2013<\/td>\r\n<td style=\"height: 18px\">Methoxy<\/td>\r\n<\/tr>\r\n<tr style=\"height: 18px\">\r\n<td style=\"height: 18px\">CH<sub>3<\/sub>CH<sub>2<\/sub>\u2013<\/td>\r\n<td style=\"height: 18px\">Ethyl<\/td>\r\n<td style=\"height: 18px\"><\/td>\r\n<td style=\"height: 18px\">CH<sub>3<\/sub>CH<sub>2<\/sub>O\u2013<\/td>\r\n<td style=\"height: 18px\">Ethoxy<\/td>\r\n<\/tr>\r\n<tr style=\"height: 18px\">\r\n<td style=\"height: 18px\">(CH<sub>3<\/sub>)<sub>2<\/sub>CH\u2013<\/td>\r\n<td style=\"height: 18px\">Isopropyl<\/td>\r\n<td style=\"height: 18px\"><\/td>\r\n<td style=\"height: 18px\">(CH<sub>3<\/sub>)<sub>2<\/sub>CHO\u2013<\/td>\r\n<td style=\"height: 18px\">Isopropoxy<\/td>\r\n<\/tr>\r\n<tr style=\"height: 18px\">\r\n<td style=\"height: 18px\">(CH<sub>3<\/sub>)<sub>3<\/sub>C\u2013<\/td>\r\n<td style=\"height: 18px\">tert-Butyl<\/td>\r\n<td style=\"height: 18px\"><\/td>\r\n<td style=\"height: 18px\">(CH<sub>3<\/sub>)<sub>3<\/sub>CO\u2013<\/td>\r\n<td style=\"height: 18px\">tert-Butoxy<\/td>\r\n<\/tr>\r\n<tr style=\"height: 18px\">\r\n<td style=\"height: 18px\">C<sub>6<\/sub>H<sub>5<\/sub>\u2013<\/td>\r\n<td style=\"height: 18px\">Phenyl<\/td>\r\n<td style=\"height: 18px\"><\/td>\r\n<td style=\"height: 18px\">C<sub>6<\/sub>H<sub>5<\/sub>O\u2013<\/td>\r\n<td style=\"height: 18px\">Phenoxy<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\nEthers are traditionally named by naming each of the two carbon groups as a separate word followed by a space and the word ether. The IUPAC system names the smaller -OR group as a substituent using the group name, alkoxy.\r\n<div>\r\n<div class=\"textbox examples\">\r\n<h3 class=\"boxtitle\">Example\u00a0 1<\/h3>\r\nCH<sub>3<\/sub>-CH<sub>2<\/sub>-O-CH<sub>3 <\/sub>is called ethyl methyl ether or methoxyethane.\r\n\r\n<\/div>\r\n<\/div>\r\nThe smaller, shorter alkyl group becomes the alkoxy substituent. The larger, longer alkyl group side becomes the alkane base name. The alkyl group on each side of the oxygen is numbered separately. The numbering priority is given to the carbon closest to the oxygen.\u00a0 For example, CH<sub>3<\/sub>CH<sub>2<\/sub>CH<sub>2<\/sub>CH<sub>2<\/sub>CH<sub>2<\/sub>-O-CH<sub>2<\/sub>CH<sub>2<\/sub>CH<sub>3<\/sub> is 1-propoxypentane. If there is cis or trans stereochemistry, the same rule still applies.\r\n<div>\r\n<div class=\"textbox examples\">\r\n<h3>Example<\/h3>\r\n<ul>\r\n \t<li>$$CH_3CH_2OCH_2CH_3$$, diethyl ether (sometimes referred to as just ether)<\/li>\r\n \t<li>$$CH_3OCH_2CH_2OCH_3$$, ethylene glycol dimethyl ether (glyme).<\/li>\r\n<\/ul>\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202638\/ethernom1.gif\" alt=\"\" width=\"406\" height=\"176\" \/>\r\n\r\n<\/div>\r\n<\/div>\r\n<div>\r\n<div class=\"textbox exercises\">\r\n<h3 class=\"boxtitle\">Exercises<\/h3>\r\nTry to name the following compounds using these conventions:\r\n\r\n<img class=\"internal\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202640\/ether1.gif\" alt=\"\" width=\"187\" height=\"80\" \/>\u00a0 <a class=\"link-https\" href=\"https:\/\/chemistry.boisestate.edu\/richardbanks\/organic\/nomenclature\/ethernomenclature2.htm\" target=\"_blank\" rel=\"external nofollow noopener\">J <\/a>\r\n\r\n<img class=\"internal\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202641\/ether2.gif\" alt=\"\" width=\"146\" height=\"65\" \/><a class=\"link-https\" href=\"https:\/\/chemistry.boisestate.edu\/richardbanks\/organic\/nomenclature\/ethernomenclature3.htm\" target=\"_blank\" rel=\"external nofollow noopener\">J <\/a>\r\n\r\nTry to draw structures for the following compounds:\r\n<ul>\r\n \t<li>2-pentyl 1-propyl ether <a class=\"link-https\" href=\"https:\/\/chemistry.boisestate.edu\/richardbanks\/organic\/nomenclature\/ethernomenclature4.htm\" target=\"_blank\" rel=\"external nofollow noopener\">J <\/a><\/li>\r\n \t<li>1-(2-propoxy)cyclopentene <a class=\"link-https\" href=\"https:\/\/chemistry.boisestate.edu\/richardbanks\/organic\/nomenclature\/ethernomenclature5.htm\" target=\"_blank\" rel=\"external nofollow noopener\">J <\/a><\/li>\r\n<\/ul>\r\n<\/div>\r\n<\/div>\r\n<div class=\"mt-section\">\r\n<h3 class=\"editable\">Common names<\/h3>\r\nSimple ethers are given common names in which the alkyl groups bonded to the oxygen are named in alphabetical order followed by the word \"ether\". Many simple ethers are symmetrical, in that the two alkyl substituents are the same. These are named as \"dialkyl ethers\".\r\n\r\n<\/div>\r\n<div class=\"mt-section\">\r\n<h3 class=\"editable\">Sulfides<\/h3>\r\nSulfur analogs of ethers (R\u2013S\u2013R') are called <strong>sulfides (or thioethers)<\/strong>, e.g., (CH<sub>3<\/sub>)<sub>3<\/sub>C\u2013S\u2013CH<sub>3<\/sub> is tert-butyl methyl sulfide. Sulfides are chemically more reactive than ethers.\r\n\r\n<\/div>\r\n<div class=\"mt-section\">\r\n<h3 class=\"editable\">References<\/h3>\r\n<ol>\r\n \t<li>Schore, Neil E. and Vollhardt, K. Peter C. <u>Organic Chemistry: Structure and Function<\/u>. New York: Bleyer, Brennan, 2007.<\/li>\r\n \t<li>Winter, Arthur. <u>Organic Chemistry for Dummies<\/u>. Hoboken, New Jersey: Wiley, 2005.<\/li>\r\n \t<li>Pellegrini, Frank. <u>Cliffs QuickReview Organic Chemistry II<\/u>. Foster City, CA: Wiley, 2000<\/li>\r\n<\/ol>\r\n<\/div>","rendered":"<section class=\"mt-content-container\">\n<div class=\"textbox learning-objectives\">\n<h3 class=\"boxtitle\">Learning Objectives<\/h3>\n<p>After completing this section, you should be able to<\/p>\n<ol>\n<li>provide the correct IUPAC name for any given alkane structure (Kekul\u00e9, condensed or shorthand).<\/li>\n<li>draw the Kekul\u00e9, condensed or shorthand structure of an alkane, given its IUPAC name.<\/li>\n<\/ol>\n<\/div>\n<div>\n<div class=\"textbox key-takeaways\">\n<h3>Key Terms<\/h3>\n<p>Make certain that you can define, and use in context, the key term below.<\/p>\n<ul>\n<li>IUPAC system<\/li>\n<\/ul>\n<\/div>\n<\/div>\n<div class=\"textbox key-takeaways\">\n<h3 class=\"boxtitle\">Study Notes<\/h3>\n<p>The IUPAC system of nomenclature aims to ensure<\/p>\n<ol>\n<li>that every organic compound has a unique, unambiguous name.<\/li>\n<li>that the IUPAC name of any compound conveys the structure of that compound to a person familiar with the system.<\/li>\n<\/ol>\n<p>One way of checking whether the name you have given to an alkane is reasonable is to count the number of carbon atoms implied by the chosen name. For example, if you named a compound 3\u2011ethyl-4\u2011methylheptane, you have indicated that the compound contains a total of 10 carbon atoms\u2014seven carbon atoms in the main chain, two carbon atoms in an ethyl group, and one carbon atom in a methyl group. If you were to check the given structure and find 11 carbon atoms, you would know that you had made a mistake. Perhaps the name you should have written was 3\u2011ethyl-4,4\u2011dimethylheptane!<\/p>\n<p>When naming alkanes, a common error of beginning students is a failure to pick out the longest carbon chain. For example, the correct name for the compound shown below is 3\u2011methylheptane, not 2\u2011ethylhexane.<\/p>\n<p class=\"max-66\"><img decoding=\"async\" class=\"aligncenter\" src=\"http:\/\/chem.libretexts.org\/@api\/deki\/files\/85405\/3-4.png?origin=mt-web\" alt=\"3-methylheptane\" \/><\/p>\n<p>Remember that every substituent must have a number, and do not forget the prefixes: di, tri, tetra, etc.<\/p>\n<p>You must use commas to separate numbers, and hyphens to separate numbers and substituents. Notice that 3\u2011methylhexane is one word.<\/p>\n<\/div>\n<h3 class=\"title editable block\">Hydrocarbons<\/h3>\n<p>The simplest class of organic compounds is the <span class=\"margin_term\"><a class=\"glossterm\">hydrocarbons<\/a><\/span>, which consist entirely of carbon and hydrogen. Petroleum and natural gas are complex, naturally occurring mixtures of many different hydrocarbons that furnish raw materials for the chemical industry. The four major classes of hydrocarbons are the following: the <span class=\"margin_term\"><a class=\"glossterm\">alkanes<\/a><\/span>, which contain only carbon\u2013hydrogen and carbon\u2013carbon single bonds; the <span class=\"margin_term\"><a class=\"glossterm\">alkenes<\/a><\/span>, which contain at least one carbon\u2013carbon double bond; the <span class=\"margin_term\"><a class=\"glossterm\">alkynes<\/a><\/span>, which contain at least one carbon\u2013carbon triple bond; and the <span class=\"margin_term\"><a class=\"glossterm\">aromatic hydrocarbons<\/a><\/span>, which usually contain rings of six carbon atoms that can be drawn with alternating single and double bonds. Alkanes are also called <em class=\"emphasis\">saturated<\/em> hydrocarbons, whereas hydrocarbons that contain multiple bonds (alkenes, alkynes, and aromatics) are <em class=\"emphasis\">unsaturated<\/em>.<\/p>\n<h2>Alkanes<\/h2>\n<p><iframe loading=\"lazy\" id=\"oembed-1\" title=\"Naming Alkanes (Simple)\" src=\"https:\/\/player.vimeo.com\/video\/181357040?dnt=1&amp;app_id=122963\" width=\"500\" height=\"281\" frameborder=\"0\"><\/iframe><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"size-thumbnail wp-image-4067 alignnone\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/26155057\/frame-11-150x150.png\" alt=\"\" width=\"150\" height=\"150\" \/><\/p>\n<p>Hydrocarbons having no double or triple bond functional groups are classified as <strong>alkanes<\/strong> or <strong>cycloalkanes<\/strong>, depending on whether the carbon atoms of the molecule are arranged only in chains or also in rings. Although these hydrocarbons have no functional groups, they constitute the framework on which functional groups are located in other classes of compounds, and provide an ideal starting point for studying and naming organic compounds. The alkanes and cycloalkanes are also members of a larger class of compounds referred to as <strong>aliphatic<\/strong>. Simply put, aliphatic compounds are compounds that do not incorporate any aromatic rings in their molecular structure.<\/p>\n<p>The following table lists the IUPAC names assigned to simple continuous-chain alkanes from C-1 to C-10. A common <strong>&#8220;ane&#8221;<\/strong> suffix identifies these compounds as alkanes. Longer chain alkanes are well known, and their names may be found in many reference and text books. The names <strong>methane<\/strong> through <strong>decane<\/strong> should be memorized, since they constitute the root of many IUPAC names. Fortunately, common numerical prefixes are used in naming chains of five or more carbon atoms.<\/p>\n<table style=\"width: 678px\" cellpadding=\"4\">\n<caption><em><strong>Table 1<\/strong>: Simple Unbranched Alkanes<\/em><\/caption>\n<thead>\n<tr style=\"background-color: #ccffcc\" align=\"center\">\n<th style=\"width: 68px\" scope=\"col\"><strong>Name<\/strong><\/th>\n<th style=\"width: 89px\" scope=\"col\"><strong>Molecular<br \/>\nFormula<\/strong><\/th>\n<th style=\"width: 116px\" scope=\"col\"><strong>Structural<br \/>\nFormula<\/strong><\/th>\n<th style=\"width: 74px\" scope=\"col\"><strong>Isomers<\/strong><\/th>\n<th style=\"width: 11px\" scope=\"col\"><\/th>\n<th style=\"width: 64px\" scope=\"col\"><strong>Name<\/strong><\/th>\n<th style=\"width: 89px\" scope=\"col\"><strong>Molecular<br \/>\nFormula<\/strong><\/th>\n<th style=\"width: 90px\" scope=\"col\"><strong>Structural<br \/>\nFormula<\/strong><\/th>\n<th style=\"width: 74px\" scope=\"col\"><strong>Isomers<\/strong><\/th>\n<\/tr>\n<\/thead>\n<tbody>\n<tr align=\"center\">\n<td style=\"width: 68px\">meth<strong>ane<\/strong><\/td>\n<td style=\"width: 89px\">CH<sub>4<\/sub><\/td>\n<td style=\"width: 116px\">CH<sub>4<\/sub><\/td>\n<td style=\"width: 74px\">1<\/td>\n<td style=\"width: 11px\"><\/td>\n<td style=\"width: 64px\">hex<strong>ane<\/strong><\/td>\n<td style=\"width: 89px\">C<sub>6<\/sub>H<sub>14<\/sub><\/td>\n<td style=\"width: 90px\">CH<sub>3<\/sub>(CH<sub>2<\/sub>)<sub>4<\/sub>CH<sub>3<\/sub><\/td>\n<td style=\"width: 74px\">5<\/td>\n<\/tr>\n<tr align=\"center\">\n<td style=\"width: 68px\">eth<strong>ane<\/strong><\/td>\n<td style=\"width: 89px\">C<sub>2<\/sub>H<sub>6<\/sub><\/td>\n<td style=\"width: 116px\">CH<sub>3<\/sub>CH<sub>3<\/sub><\/td>\n<td style=\"width: 74px\">1<\/td>\n<td style=\"width: 11px\"><\/td>\n<td style=\"width: 64px\">hept<strong>ane<\/strong><\/td>\n<td style=\"width: 89px\">C<sub>7<\/sub>H<sub>16<\/sub><\/td>\n<td style=\"width: 90px\">CH<sub>3<\/sub>(CH<sub>2<\/sub>)<sub>5<\/sub>CH<sub>3<\/sub><\/td>\n<td style=\"width: 74px\">9<\/td>\n<\/tr>\n<tr align=\"center\">\n<td style=\"width: 68px\">prop<strong>ane<\/strong><\/td>\n<td style=\"width: 89px\">C<sub>3<\/sub>H<sub>8<\/sub><\/td>\n<td style=\"width: 116px\">CH<sub>3<\/sub>CH<sub>2<\/sub>CH<sub>3<\/sub><\/td>\n<td style=\"width: 74px\">1<\/td>\n<td style=\"width: 11px\"><\/td>\n<td style=\"width: 64px\">oct<strong>ane<\/strong><\/td>\n<td style=\"width: 89px\">C<sub>8<\/sub>H<sub>18<\/sub><\/td>\n<td style=\"width: 90px\">CH<sub>3<\/sub>(CH<sub>2<\/sub>)<sub>6<\/sub>CH<sub>3<\/sub><\/td>\n<td style=\"width: 74px\">18<\/td>\n<\/tr>\n<tr align=\"center\">\n<td style=\"width: 68px\">but<strong>ane<\/strong><\/td>\n<td style=\"width: 89px\">C<sub>4<\/sub>H<sub>10<\/sub><\/td>\n<td style=\"width: 116px\">CH<sub>3<\/sub>CH<sub>2<\/sub>CH<sub>2<\/sub>CH<sub>3<\/sub><\/td>\n<td style=\"width: 74px\">2<\/td>\n<td style=\"width: 11px\"><\/td>\n<td style=\"width: 64px\">non<strong>ane<\/strong><\/td>\n<td style=\"width: 89px\">C<sub>9<\/sub>H<sub>20<\/sub><\/td>\n<td style=\"width: 90px\">CH<sub>3<\/sub>(CH<sub>2<\/sub>)<sub>7<\/sub>CH<sub>3<\/sub><\/td>\n<td style=\"width: 74px\">35<\/td>\n<\/tr>\n<tr align=\"center\">\n<td style=\"width: 68px\">pent<strong>ane<\/strong><\/td>\n<td style=\"width: 89px\">C<sub>5<\/sub>H<sub>12<\/sub><\/td>\n<td style=\"width: 116px\">CH<sub>3<\/sub>(CH<sub>2<\/sub>)<sub>3<\/sub>CH<sub>3<\/sub><\/td>\n<td style=\"width: 74px\">3<\/td>\n<td style=\"width: 11px\"><\/td>\n<td style=\"width: 64px\">dec<strong>ane<\/strong><\/td>\n<td style=\"width: 89px\">C<sub>10<\/sub>H<sub>22<\/sub><\/td>\n<td style=\"width: 90px\">CH<sub>3<\/sub>(CH<sub>2<\/sub>)<sub>8<\/sub>CH<sub>3<\/sub><\/td>\n<td style=\"width: 74px\">75<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<div>\n<div class=\"textbox key-takeaways\">\n<div>\n<h3 class=\"boxtitle\">Some important behavior trends and terminologies<\/h3>\n<ol>\n<li>The formulas and structures of these alkanes increase uniformly by a CH<sub>2<\/sub> increment.<\/li>\n<li>A uniform variation of this kind in a series of compounds is called <strong>homologous<\/strong>.<\/li>\n<li>These formulas all fit the <strong>C<sub>n<\/sub>H<sub>2n<\/sub><sub>+2<\/sub><\/strong> rule (for acyclic aka non-cyclic) alkanes. This is also the highest possible H\/C ratio for a stable hydrocarbon.<\/li>\n<li>Since the H\/C ratio in these compounds is at a maximum, we call them <strong>saturated<\/strong> (with hydrogen).<\/li>\n<\/ol>\n<\/div>\n<\/div>\n<section class=\"mt-content-container\">\n<div class=\"mt-section\">\n<div id=\"averill_1.0-ch02_s04_s02_s04\" class=\"section\">\n<div class=\"mt-section\">\n<h3 class=\"title editable block\">Cyclic hydrocarbons<\/h3>\n<p id=\"averill_1.0-ch02_s04_s02_s04_p01\" class=\"para editable block\">In a cyclic hydrocarbon, the ends of a hydrocarbon chain are connected to form a ring of covalently bonded carbon atoms. Cyclic hydrocarbons are named by attaching the prefix <em class=\"emphasis\">cyclo<\/em>&#8211; to the name of the alkane, the alkene, or the alkyne. The simplest cyclic alkanes are <em class=\"emphasis\">cyclopropane<\/em> (C<sub class=\"subscript\">3<\/sub>H<sub class=\"subscript\">6<\/sub>) a flammable gas that is also a powerful anesthetic, and <em class=\"emphasis\">cyclobutane<\/em> (C<sub class=\"subscript\">4<\/sub>H<sub class=\"subscript\">8<\/sub>) (part (c) in <span class=\"xref external\">Figure 3.7.2<\/span>). The most common way to draw the structures of cyclic alkanes is to sketch a polygon with the same number of vertices as there are carbon atoms in the ring; each vertex represents a CH<sub class=\"subscript\">2<\/sub> unit. The structures of the cycloalkanes that contain three to six carbon atoms are shown schematically in <span class=\"xref external\">the figure below:<br \/>\n<\/span><\/p>\n<div id=\"averill_1.0-ch02_s04_s02_s04_f01\" class=\"figure large medium-height editable block\">\n<div style=\"width: 504px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" class=\"internal\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202703\/90bd930211dd9973f28d67347758d8ce.jpg\" alt=\"\" width=\"494\" height=\"364\" \/><\/p>\n<p class=\"wp-caption-text\"><em>The simple cycloalkanes<\/em><\/p>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<h3 class=\"editable\">Alkyl groups<a class=\"mt-disabled\" title=\"Edit section\" rel=\"broken\"><span class=\"icon\"><img decoding=\"async\" class=\"sectionedit\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202603\/icon-trans.gif\" alt=\"Edit section\" \/><\/span><\/a><\/h3>\n<p class=\"paragraph\">Acyclic <a class=\"internal\" title=\"Organic Chemistry\/Hydrocarbons\/Alkanes\" href=\"\/Organic_Chemistry\/Hydrocarbons\/Alkanes\" rel=\"internal\">alkanes <\/a>can be described by the general formula C<sub class=\"subscript\">n<\/sub>H<sub class=\"subscript\">2n<\/sub><sub class=\"subscript\">+2<\/sub>. An alkyl group is formed by removing one hydrogen from the alkane chain and is described by the formula C<sub class=\"subscript\">n<\/sub>H<sub class=\"subscript\">2n<\/sub><sub class=\"subscript\">+1<\/sub>. The removal of this hydrogen results in a stem change from <strong class=\"bold\">-ane<\/strong> to <strong class=\"bold\">-yl<\/strong>. Take a look at the following examples.<img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-4750\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/06062115\/Alkyls.png\" alt=\"\" width=\"388\" height=\"152\" \/><\/p>\n<\/div>\n<\/section>\n<section class=\"mt-content-container\">\n<div class=\"mt-section\">\n<p class=\"paragraph\">The same concept can be applied to any of the straight chain alkane names provided in the table above.\u00a0 Examples of some common <strong>alkyl groups<\/strong> are given in the following table. Note that the &#8220;ane&#8221; suffix is replaced by &#8220;<strong>yl<\/strong>&#8221; in naming groups. The symbol <strong>R<\/strong> is used to designate a generic (unspecified) alkyl group.<\/p>\n<table cellpadding=\"5\">\n<caption><em><strong>Table 2<\/strong>: Alkyl Groups Names<\/em><\/caption>\n<tbody>\n<tr align=\"center\" valign=\"middle\">\n<th scope=\"row\">Group<\/th>\n<td>CH<sub>3<\/sub>\u2013<\/td>\n<td>C<sub>2<\/sub>H<sub>5<\/sub>\u2013<\/td>\n<td>CH<sub>3<\/sub>CH<sub>2<\/sub>CH<sub>2<\/sub>\u2013<\/td>\n<td>(CH<sub>3<\/sub>)<sub>2<\/sub>CH\u2013<\/td>\n<td>CH<sub>3<\/sub>CH<sub>2<\/sub>CH<sub>2<\/sub>CH<sub>2<\/sub>\u2013<\/td>\n<td>(CH<sub>3<\/sub>)<sub>2<\/sub>CHCH<sub>2<\/sub>\u2013<\/td>\n<td>CH<sub>3<\/sub>CH<sub>2<\/sub>CH(CH<sub>3<\/sub>)\u2013<\/td>\n<td>(CH<sub>3<\/sub>)<sub>3<\/sub>C\u2013<\/td>\n<td>R\u2013<\/td>\n<\/tr>\n<tr align=\"center\" valign=\"middle\">\n<th scope=\"row\">Name<\/th>\n<td>Methyl<\/td>\n<td>Ethyl<\/td>\n<td>Propyl<\/td>\n<td>Isopropyl<\/td>\n<td>Butyl<\/td>\n<td>Isobutyl<\/td>\n<td>sec-Butyl<\/td>\n<td>tert-Butyl<\/td>\n<td>\u00a0 Alkyl<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p>Similarly, groups of atoms derived from aromatic hydrocarbons are <em class=\"emphasis\">aryl groups<\/em>, which sometimes have unexpected names. For example, the \u2013C<sub class=\"subscript\">6<\/sub>H<sub class=\"subscript\">5<\/sub> fragment is derived from benzene, but it is called a <em class=\"emphasis\">phenyl<\/em> group. In general formulas and structures, alkyl and aryl groups are often abbreviated as <span class=\"margin_term\"><a class=\"glossterm\">R<\/a><\/span>.<a title=\"90d23185727828608152de77268572b8.jpg\" href=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/30410\/90d23185727828608152de77268572b8.jpg?revision=3\" rel=\"internal\"><img loading=\"lazy\" decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202726\/90d23185727828608152de77268572b8.jpg\" alt=\"\" width=\"237\" height=\"196\" \/><\/a><\/p>\n<h3>Naming complex alkanes<\/h3>\n<p><iframe loading=\"lazy\" id=\"oembed-2\" title=\"Naming Alkanes (Complex)\" src=\"https:\/\/player.vimeo.com\/video\/183372579?dnt=1&amp;app_id=122963\" width=\"500\" height=\"281\" frameborder=\"0\"><\/iframe><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"size-thumbnail wp-image-4068 alignnone\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/26155149\/frame-12-150x150.png\" alt=\"\" width=\"150\" height=\"150\" \/><\/p>\n<p>Beginning with butane (C<sub>4<\/sub>H<sub>10<\/sub>), and becoming more numerous with larger alkanes, we note the existence of alkane isomers. For example, there are five C<sub>6<\/sub>H<sub>14<\/sub> isomers, shown below as abbreviated line formulas (<strong>A<\/strong> through E):<\/p>\n<\/div>\n<\/section>\n<\/div>\n<p style=\"text-align: center\"><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202602\/c6h14.gif\" alt=\"c6h14.gif\" \/><\/p>\n<p>Although these distinct compounds all have the same molecular formula, only one (<strong>A<\/strong>) can be called hexane. How then are we to name the others?\u00a0 (Answers below.)<\/p>\n<p>The <strong>IUPAC<\/strong> system requires first that we have names for simple unbranched chains, as noted above, and second that we have names for simple alkyl groups that may be attached to the chains. Examples of some common <strong>alkyl groups<\/strong> are given in the following table. Note that the &#8220;ane&#8221; suffix is replaced by &#8220;<strong>yl<\/strong>&#8221; in naming groups. The symbol <strong>R<\/strong> is used to designate a generic (unspecified) alkyl group.<\/p>\n<div class=\"mt-section\">\n<h4 class=\"editable\">IUPAC Rules for Alkane Nomenclature<\/h4>\n<\/div>\n<ol>\n<li>\u00a0Find and name the longest continuous carbon chain.<\/li>\n<li>\u00a0Identify and name groups attached to this chain.<\/li>\n<li>\u00a0Number the chain consecutively, starting at the end nearest a substituent group.<\/li>\n<li>\u00a0Designate the location of each substituent group by an appropriate number and name.<\/li>\n<li>\u00a0Assemble the name, listing groups in alphabetical order.<\/li>\n<li>\u00a0The prefixes di, tri, tetra etc., used to designate several groups of the same kind, are not considered when alphabetizing.<\/li>\n<\/ol>\n<p>For the above isomers of hexane the IUPAC names are: \u00a0 B\u00a0 2-methylpentane\u00a0\u00a0\u00a0 C\u00a0 3-methylpentane\u00a0\u00a0\u00a0 D\u00a0 2,2-dimethylbutane\u00a0\u00a0\u00a0 E\u00a0 2,3-dimethylbutane.<\/p>\n<h2>Naming alkyl halides<\/h2>\n<p><strong>Halogen substituents<\/strong> are easily accommodated, using the names: fluoro (F-), chloro (Cl-), bromo (Br-) and iodo (I-).\u00a0 These are inserted alphabetically into the name in the same way as alkyl groups are included when naming complex alkanes.<\/p>\n<div>\n<div class=\"textbox examples\">\n<h3 class=\"boxtitle\">Example: Halogen Substitution<\/h3>\n<p>For example, (CH<sub>3<\/sub>)<sub>2<\/sub>CHCH<sub>2<\/sub>CH<sub>2<\/sub>Br would be named 1-bromo-3-methylbutane. If the halogen is bonded to a simple alkyl group an alternative &#8220;alkyl halide&#8221; name may be used. Thus, C<sub>2<\/sub>H<sub>5<\/sub>Cl may be named chloroethane (no locator number is needed for a two carbon chain) or ethyl chloride.<\/p>\n<\/div>\n<\/div>\n<\/section>\n<section class=\"mt-content-container\">\n<div class=\"mt-section\">\n<div class=\"mt-page-section\">\n<div class=\"mt-section\">\n<div>\n<div class=\"textbox exercises\">\n<h3>Example<\/h3>\n<p class=\"paragraph\">What is the name of the following molecule?<\/p>\n<p class=\"paragraph\"><img loading=\"lazy\" decoding=\"async\" class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202608\/NamingAlkanes-Numbering_01.gif\" alt=\"NamingAlkanes-Numbering 01.gif\" width=\"257\" height=\"114\" \/><\/p>\n<p class=\"paragraph\">\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q317866\">Show Solution<\/span><\/p>\n<div id=\"q317866\" class=\"hidden-answer\" style=\"display: none\">\n<p class=\"paragraph\"><strong class=\"bold\">Step #1:<\/strong> Choose the longest, most substituted carbon chain containing a functional group. This example does not contain any functional groups, so we only need to be concerned with choosing the longest, most substituted carbon chain. The longest carbon chain has been highlighted in red and consists of eight carbons.<\/p>\n<p class=\"paragraph\"><img loading=\"lazy\" decoding=\"async\" class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202610\/NamingAlkanes-Numbering_02.gif\" alt=\"NamingAlkanes-Numbering 02.gif\" width=\"301\" height=\"134\" \/><\/p>\n<p class=\"paragraph\"><strong class=\"bold\">Step #2:<\/strong> Carbons bonded to a functional group must have the lowest possible carbon number. If there are no functional groups, then any substituent present must have the lowest possible number.\u00a0Because this example does not contain any functional groups, we only need to be concerned with the two substituents present, that is, the two methyl groups. If we begin numbering the chain from the left, the methyls would be assigned the numbers 4 and 7, respectively. If we begin numbering the chain from the right, the methyls would be assigned the numbers 2 and 5. Therefore, to satisfy the second rule, numbering begins on the right side of the carbon chain as shown below. This gives the methyl groups the lowest possible numbering.<\/p>\n<p class=\"paragraph\"><img loading=\"lazy\" decoding=\"async\" class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202612\/NamingAlkanes-Numbering_03.gif\" alt=\"NamingAlkanes-Numbering 03.GIF\" width=\"311\" height=\"134\" \/><\/p>\n<p class=\"paragraph\"><strong>Alphebetization: <\/strong>In this example, there is no need to utilize the third rule.\u00a0Because the two substituents are identical, neither takes alphabetical precedence with respect to numbering the carbons. This concept will become clearer in the following examples.<\/p>\n<p class=\"paragraph\">The name of this molecule is thus: <strong>2,5-dimethyloctane<\/strong><\/p>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div>\n<div class=\"textbox exercises\">\n<h3>Example<\/h3>\n<p class=\"paragraph\">What is the name of the following molecule?<\/p>\n<p class=\"paragraph\"><img loading=\"lazy\" decoding=\"async\" class=\"internal\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202614\/NamingAlkanes-Numbering_08DSL.gif\" alt=\"\" width=\"269\" height=\"119\" \/><\/p>\n<p class=\"paragraph\">\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q794732\">Show Solution<\/span><\/p>\n<div id=\"q794732\" class=\"hidden-answer\" style=\"display: none\">\n<p class=\"paragraph\"><strong class=\"bold\">Step #1<\/strong>: Choose the longest, most substituted carbon chain containing a functional group. This example contains two functional groups, bromine and chlorine. The longest carbon chain has been highlighted in red and consists of seven carbons.<\/p>\n<p class=\"paragraph\"><img loading=\"lazy\" decoding=\"async\" class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202616\/NamingAlkanes-Numbering_05.gif\" alt=\"NamingAlkanes-Numbering 05.GIF\" width=\"269\" height=\"108\" \/><\/p>\n<p class=\"paragraph\"><strong class=\"bold\">Step #2:<\/strong> Carbons bonded to a functional group must have the lowest possible carbon number. If there are no functional groups, then any substituent present must have the lowest possible number. In this example, numbering the chain from the left or the right would satisfy this rule. If we number the chain from the left, bromine and chlorine would be assigned the second and sixth carbon positions, respectively. If we number the chain from the right, chlorine would be assigned the second position and bromine would be assigned the sixth position. In other words, whether we choose to number from the left or right, the functional groups occupy the second and sixth positions in the chain. To select the correct numbering scheme, we need to utilize the third rule.<\/p>\n<p class=\"paragraph\"><img loading=\"lazy\" decoding=\"async\" class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202618\/NamingAlkanes-Numbering_06.gif\" alt=\"NamingAlkanes-Numbering 06.GIF\" width=\"608\" height=\"108\" \/><\/p>\n<p class=\"paragraph\"><strong class=\"bold\">Alphabetizing:<\/strong> After applying the first two rules, take the alphabetical order into consideration. Alphabetically, bromine comes before chlorine. Therefore, bromine is assigned the second carbon position, and chlorine is assigned the sixth carbon position.<\/p>\n<p class=\"paragraph\"><img loading=\"lazy\" decoding=\"async\" class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202620\/NamingAlkanes-Numbering_07.gif\" alt=\"NamingAlkanes-Numbering 07.GIF\" width=\"269\" height=\"108\" \/><\/p>\n<p class=\"paragraph mt-align-left\">The name of this molecule is thus: <strong>2-bromo-6-chloroheptane<\/strong><\/p>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div>\n<div class=\"textbox exercises\">\n<h3>Example<\/h3>\n<p class=\"paragraph\">What is the name of the following molecule?<\/p>\n<p class=\"paragraph\"><img loading=\"lazy\" decoding=\"async\" class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202622\/NamingAlkanes-Numbering_08.gif\" alt=\"NamingAlkanes-Numbering 08.GIF\" width=\"269\" height=\"119\" \/><\/p>\n<p class=\"paragraph\">\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q597266\">Show Solution<\/span><\/p>\n<div id=\"q597266\" class=\"hidden-answer\" style=\"display: none\">\n<p class=\"paragraph\"><strong class=\"bold\">Step #1<\/strong>: Choose the longest, most substituted carbon chain containing a functional group. This example contains two functional groups, bromine and chlorine, and one substitute, the methyl group. The longest carbon chain has been highlighted in red and consists of seven carbons.<\/p>\n<p class=\"paragraph\"><img loading=\"lazy\" decoding=\"async\" class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202624\/NamingAlkanes-Numbering_09.gif\" alt=\"NamingAlkanes-Numbering 09.GIF\" width=\"269\" height=\"119\" \/><\/p>\n<p class=\"paragraph\"><strong class=\"bold\">Step #2:<\/strong> Carbons bonded to a functional group must have the lowest possible carbon number. After taking functional groups into consideration, any substituents present must have the lowest possible carbon number. This particular example illustrates the <strong class=\"bold\">point of difference principle<\/strong>. If we number the chain from the left, bromine, the methyl group and chlorine would occupy the second, fifth and sixth positions, respectively. This concept is illustrated in the second drawing below. If we number the chain from the right, chlorine, the methyl group and bromine would occupy the second, third and sixth positions, respectively, which\u00a0is illustrated in the first drawing below. The position of the methyl, therefore, becomes a <strong class=\"bold\">point of difference<\/strong>. In the first drawing, the methyl\u00a0occupies the third position. In the second drawing, the methyl occupies the fifth position. To satisfy the second rule, we want to choose the numbering scheme that provides the lowest possible numbering of this substituent. Therefore, the first of the two carbon chains shown below is correct.<\/p>\n<p class=\"paragraph\"><img loading=\"lazy\" decoding=\"async\" class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202626\/NamingAlkanes-Numbering_10.gif\" alt=\"NamingAlkanes-Numbering 10.GIF\" width=\"269\" height=\"243\" \/><\/p>\n<p class=\"paragraph\">Therefore,\u00a0the first numbering scheme is the appropriate one to use.<\/p>\n<p class=\"paragraph\"><img loading=\"lazy\" decoding=\"async\" class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202627\/NamingAlkanes-Naming_01.gif\" alt=\"NamingAlkanes-Naming 01.GIF\" width=\"269\" height=\"108\" \/><\/p>\n<p class=\"paragraph\">Once you have determined the correct numbering of the carbons, it is often useful to make a list, including the functional groups, substitutes, and the name of the parent chain.<\/p>\n<p class=\"paragraph\"><strong class=\"bold\">Alphabetization:<\/strong> After applying the first two rules, take the alphabetical order into consideration. Alphabetically, bromine comes before chlorine. Therefore, bromine is assigned the second carbon position, and chlorine is assigned the sixth carbon position.<\/p>\n<p class=\"paragraph\">Parent chain: heptane 2-Chloro 3-Methyl 6-Bromo<\/p>\n<p class=\"paragraph\" style=\"text-align: center\">6-bromo-2-chloro-3-methylheptane<\/p>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div class=\"mt-section\">\n<div class=\"textbox exercises\">\n<h3>Exercises<\/h3>\n<div id=\"s61690\" class=\"mt-include\">\n<div id=\"section_14\" class=\"mt-section\">\n<div id=\"section_15\" class=\"mt-section\">\n<h4 id=\"Questions-61690\">Question<\/h4>\n<p><span class=\"mt-font-Times New Roman,serif\"><span class=\"mt-font-size-12.0pt\">Give the name of the following molecules:<\/span><\/span><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202633\/3.42.png\" alt=\"\" width=\"455\" height=\"279\" \/><\/p>\n<\/div>\n<div id=\"section_16\" class=\"mt-section\">\n<p>&nbsp;<\/p>\n<p id=\"Solutions-61690\">\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q785873\">Show Solutions<\/span><\/p>\n<div id=\"q785873\" class=\"hidden-answer\" style=\"display: none\">\n<p><span class=\"mt-font-Times New Roman,serif\"><span class=\"mt-font-size-12.0pt\">1 is 3,4-Dimethylhexane<\/span><\/span><\/p>\n<p><span class=\"mt-font-Times New Roman,serif\"><span class=\"mt-font-size-12.0pt\">2 is 2-methylpentane<\/span><\/span><\/p>\n<p><span class=\"mt-font-Times New Roman,serif\"><span class=\"mt-font-size-12.0pt\">3 is 2,2,4-trimethylpentane<\/span><\/span><\/p>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div class=\"mt-section\">\n<h2>Naming ethers<\/h2>\n<section class=\"mt-content-container\">Ethers are compounds having two alkyl or aryl groups bonded to an oxygen atom, as in the formula R<sup>1<\/sup>\u2013O\u2013R<sup>2<\/sup>. The ether functional group does not have a characteristic IUPAC nomenclature suffix, so it is necessary to designate it as a substituent. To do so the common alkoxy substituents are given names derived from their alkyl component (below):<\/section>\n<\/div>\n<\/div>\n<\/section>\n<table style=\"margin: auto\" cellpadding=\"5\">\n<thead>\n<tr style=\"height: 15px\">\n<th style=\"background-color: #ddffdd;height: 15px\" scope=\"col\">Alkyl Group<\/th>\n<th style=\"background-color: #ddffdd;height: 15px\" scope=\"col\">Name<\/th>\n<th style=\"height: 15px\" scope=\"col\"><\/th>\n<th style=\"background-color: #ddddff;height: 15px\" scope=\"col\">Alkoxy Group<\/th>\n<th style=\"background-color: #ddddff;height: 15px\" scope=\"col\">Name<\/th>\n<\/tr>\n<\/thead>\n<tbody>\n<tr style=\"height: 18px\">\n<td style=\"height: 18px\">CH<sub>3<\/sub>\u2013<\/td>\n<td style=\"height: 18px\">Methyl<\/td>\n<td style=\"height: 18px\"><\/td>\n<td style=\"height: 18px\">CH<sub>3<\/sub>O\u2013<\/td>\n<td style=\"height: 18px\">Methoxy<\/td>\n<\/tr>\n<tr style=\"height: 18px\">\n<td style=\"height: 18px\">CH<sub>3<\/sub>CH<sub>2<\/sub>\u2013<\/td>\n<td style=\"height: 18px\">Ethyl<\/td>\n<td style=\"height: 18px\"><\/td>\n<td style=\"height: 18px\">CH<sub>3<\/sub>CH<sub>2<\/sub>O\u2013<\/td>\n<td style=\"height: 18px\">Ethoxy<\/td>\n<\/tr>\n<tr style=\"height: 18px\">\n<td style=\"height: 18px\">(CH<sub>3<\/sub>)<sub>2<\/sub>CH\u2013<\/td>\n<td style=\"height: 18px\">Isopropyl<\/td>\n<td style=\"height: 18px\"><\/td>\n<td style=\"height: 18px\">(CH<sub>3<\/sub>)<sub>2<\/sub>CHO\u2013<\/td>\n<td style=\"height: 18px\">Isopropoxy<\/td>\n<\/tr>\n<tr style=\"height: 18px\">\n<td style=\"height: 18px\">(CH<sub>3<\/sub>)<sub>3<\/sub>C\u2013<\/td>\n<td style=\"height: 18px\">tert-Butyl<\/td>\n<td style=\"height: 18px\"><\/td>\n<td style=\"height: 18px\">(CH<sub>3<\/sub>)<sub>3<\/sub>CO\u2013<\/td>\n<td style=\"height: 18px\">tert-Butoxy<\/td>\n<\/tr>\n<tr style=\"height: 18px\">\n<td style=\"height: 18px\">C<sub>6<\/sub>H<sub>5<\/sub>\u2013<\/td>\n<td style=\"height: 18px\">Phenyl<\/td>\n<td style=\"height: 18px\"><\/td>\n<td style=\"height: 18px\">C<sub>6<\/sub>H<sub>5<\/sub>O\u2013<\/td>\n<td style=\"height: 18px\">Phenoxy<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p>Ethers are traditionally named by naming each of the two carbon groups as a separate word followed by a space and the word ether. The IUPAC system names the smaller -OR group as a substituent using the group name, alkoxy.<\/p>\n<div>\n<div class=\"textbox examples\">\n<h3 class=\"boxtitle\">Example\u00a0 1<\/h3>\n<p>CH<sub>3<\/sub>-CH<sub>2<\/sub>-O-CH<sub>3 <\/sub>is called ethyl methyl ether or methoxyethane.<\/p>\n<\/div>\n<\/div>\n<p>The smaller, shorter alkyl group becomes the alkoxy substituent. The larger, longer alkyl group side becomes the alkane base name. The alkyl group on each side of the oxygen is numbered separately. The numbering priority is given to the carbon closest to the oxygen.\u00a0 For example, CH<sub>3<\/sub>CH<sub>2<\/sub>CH<sub>2<\/sub>CH<sub>2<\/sub>CH<sub>2<\/sub>-O-CH<sub>2<\/sub>CH<sub>2<\/sub>CH<sub>3<\/sub> is 1-propoxypentane. If there is cis or trans stereochemistry, the same rule still applies.<\/p>\n<div>\n<div class=\"textbox examples\">\n<h3>Example<\/h3>\n<ul>\n<li>$$CH_3CH_2OCH_2CH_3$$, diethyl ether (sometimes referred to as just ether)<\/li>\n<li>$$CH_3OCH_2CH_2OCH_3$$, ethylene glycol dimethyl ether (glyme).<\/li>\n<\/ul>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202638\/ethernom1.gif\" alt=\"\" width=\"406\" height=\"176\" \/><\/p>\n<\/div>\n<\/div>\n<div>\n<div class=\"textbox exercises\">\n<h3 class=\"boxtitle\">Exercises<\/h3>\n<p>Try to name the following compounds using these conventions:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202640\/ether1.gif\" alt=\"\" width=\"187\" height=\"80\" \/>\u00a0 <a class=\"link-https\" href=\"https:\/\/chemistry.boisestate.edu\/richardbanks\/organic\/nomenclature\/ethernomenclature2.htm\" target=\"_blank\" rel=\"external nofollow noopener\">J <\/a><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/19202641\/ether2.gif\" alt=\"\" width=\"146\" height=\"65\" \/><a class=\"link-https\" href=\"https:\/\/chemistry.boisestate.edu\/richardbanks\/organic\/nomenclature\/ethernomenclature3.htm\" target=\"_blank\" rel=\"external nofollow noopener\">J <\/a><\/p>\n<p>Try to draw structures for the following compounds:<\/p>\n<ul>\n<li>2-pentyl 1-propyl ether <a class=\"link-https\" href=\"https:\/\/chemistry.boisestate.edu\/richardbanks\/organic\/nomenclature\/ethernomenclature4.htm\" target=\"_blank\" rel=\"external nofollow noopener\">J <\/a><\/li>\n<li>1-(2-propoxy)cyclopentene <a class=\"link-https\" href=\"https:\/\/chemistry.boisestate.edu\/richardbanks\/organic\/nomenclature\/ethernomenclature5.htm\" target=\"_blank\" rel=\"external nofollow noopener\">J <\/a><\/li>\n<\/ul>\n<\/div>\n<\/div>\n<div class=\"mt-section\">\n<h3 class=\"editable\">Common names<\/h3>\n<p>Simple ethers are given common names in which the alkyl groups bonded to the oxygen are named in alphabetical order followed by the word &#8220;ether&#8221;. Many simple ethers are symmetrical, in that the two alkyl substituents are the same. These are named as &#8220;dialkyl ethers&#8221;.<\/p>\n<\/div>\n<div class=\"mt-section\">\n<h3 class=\"editable\">Sulfides<\/h3>\n<p>Sulfur analogs of ethers (R\u2013S\u2013R&#8217;) are called <strong>sulfides (or thioethers)<\/strong>, e.g., (CH<sub>3<\/sub>)<sub>3<\/sub>C\u2013S\u2013CH<sub>3<\/sub> is tert-butyl methyl sulfide. Sulfides are chemically more reactive than ethers.<\/p>\n<\/div>\n<div class=\"mt-section\">\n<h3 class=\"editable\">References<\/h3>\n<ol>\n<li>Schore, Neil E. and Vollhardt, K. Peter C. <u>Organic Chemistry: Structure and Function<\/u>. New York: Bleyer, Brennan, 2007.<\/li>\n<li>Winter, Arthur. <u>Organic Chemistry for Dummies<\/u>. Hoboken, New Jersey: Wiley, 2005.<\/li>\n<li>Pellegrini, Frank. <u>Cliffs QuickReview Organic Chemistry II<\/u>. Foster City, CA: Wiley, 2000<\/li>\n<\/ol>\n<\/div>\n\n\t\t\t <section class=\"citations-section\" role=\"contentinfo\">\n\t\t\t <h3>Candela Citations<\/h3>\n\t\t\t\t\t <div>\n\t\t\t\t\t\t <div id=\"citation-list-2335\">\n\t\t\t\t\t\t\t <div class=\"licensing\"><div class=\"license-attribution-dropdown-subheading\">CC licensed content, Shared previously<\/div><ul class=\"citation-list\"><li>3.4 Naming Alkanes. <strong>Authored by<\/strong>: Dr. Dietmar Kennepohl FCIC (Professor of Chemistry, Athabasca University), Prof. Steven Farmer (Sonoma State University), Tim Soderbergu00a0(University of Minnesota, Morris). <strong>Located at<\/strong>: <a target=\"_blank\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Map%3A_Organic_Chemistry_(McMurry)\/Chapter_03%3A_Organic_Compounds%3A_Alkanes_and_Their_Stereochemistry\/3.4_Naming_Alkanes\">https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Map%3A_Organic_Chemistry_(McMurry)\/Chapter_03%3A_Organic_Compounds%3A_Alkanes_and_Their_Stereochemistry\/3.4_Naming_Alkanes<\/a>. <strong>Project<\/strong>: Chemistry LibreTexts. <strong>License<\/strong>: <em><a target=\"_blank\" rel=\"license\" href=\"https:\/\/creativecommons.org\/licenses\/by-nc-sa\/4.0\/\">CC BY-NC-SA: Attribution-NonCommercial-ShareAlike<\/a><\/em><\/li><li>Nomenclature of Ethers. <strong>Authored by<\/strong>: William Reusch, Richard Banks. <strong>Located at<\/strong>: <a target=\"_blank\" href=\"https:\/\/chem.libretexts.org\/Core\/Organic_Chemistry\/Ethers\/Nomenclature_of_Ethers\">https:\/\/chem.libretexts.org\/Core\/Organic_Chemistry\/Ethers\/Nomenclature_of_Ethers<\/a>. <strong>Project<\/strong>: Chemistry LibreTexts. <strong>License<\/strong>: <em><a target=\"_blank\" rel=\"license\" href=\"https:\/\/creativecommons.org\/licenses\/by-nc-sa\/4.0\/\">CC BY-NC-SA: Attribution-NonCommercial-ShareAlike<\/a><\/em><\/li><li>3.7: Names of Formulas of Organic Compounds. <strong>Located at<\/strong>: <a target=\"_blank\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/General_Chemistry\/Map%3A_General_Chemistry_(Petrucci_et_al.)\/03%3A_Chemical_Compounds\/3.7%3A__Names_of_Formulas_of_Organic_Compounds\">https:\/\/chem.libretexts.org\/Textbook_Maps\/General_Chemistry\/Map%3A_General_Chemistry_(Petrucci_et_al.)\/03%3A_Chemical_Compounds\/3.7%3A__Names_of_Formulas_of_Organic_Compounds<\/a>. <strong>Project<\/strong>: Chemistry LibreTexts. <strong>License<\/strong>: <em><a target=\"_blank\" rel=\"license\" href=\"https:\/\/creativecommons.org\/licenses\/by-nc-sa\/4.0\/\">CC BY-NC-SA: Attribution-NonCommercial-ShareAlike<\/a><\/em><\/li><\/ul><\/div>\n\t\t\t\t\t\t <\/div>\n\t\t\t\t\t <\/div>\n\t\t\t <\/section>","protected":false},"author":311,"menu_order":1,"template":"","meta":{"_candela_citation":"[{\"type\":\"cc\",\"description\":\"3.4 Naming Alkanes\",\"author\":\"Dr. Dietmar Kennepohl FCIC (Professor of Chemistry, Athabasca University), Prof. Steven Farmer (Sonoma State University), Tim Soderbergu00a0(University of Minnesota, Morris)\",\"organization\":\"\",\"url\":\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Map%3A_Organic_Chemistry_(McMurry)\/Chapter_03%3A_Organic_Compounds%3A_Alkanes_and_Their_Stereochemistry\/3.4_Naming_Alkanes\",\"project\":\"Chemistry LibreTexts\",\"license\":\"cc-by-nc-sa\",\"license_terms\":\"\"},{\"type\":\"cc\",\"description\":\"Nomenclature of Ethers\",\"author\":\"William Reusch, Richard Banks\",\"organization\":\"\",\"url\":\"https:\/\/chem.libretexts.org\/Core\/Organic_Chemistry\/Ethers\/Nomenclature_of_Ethers\",\"project\":\"Chemistry 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