{"id":669,"date":"2017-10-04T21:11:44","date_gmt":"2017-10-04T21:11:44","guid":{"rendered":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/?post_type=chapter&#038;p=669"},"modified":"2017-10-24T15:38:22","modified_gmt":"2017-10-24T15:38:22","slug":"nomenclature-of-alkanes","status":"publish","type":"chapter","link":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/chapter\/nomenclature-of-alkanes\/","title":{"raw":"Nomenclature of Alkanes","rendered":"Nomenclature of Alkanes"},"content":{"raw":"<div class=\"elm-header\">\r\n<div class=\"elm-header-custom\">\r\n<div class=\"textbox learning-objectives\">\r\n<h3>Objectives<\/h3>\r\n<div id=\"elm-main-content\" class=\"elm-content-container\">\r\n<div>\r\n<div id=\"skills\">\r\n\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>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"elm-main-content\" class=\"elm-content-container\">\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 id=\"note\">\r\n<div class=\"textbox\">\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\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>\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><img src=\"https:\/\/chem.libretexts.org\/LibreTexts\/Athabasca_University\/Chemistry_350%3A_Organic_Chemistry_I\/Chapter_3%3A_Organic_Compounds%3A_Alkanes_and_Their_Stereochemistry\/\/LibreTexts\/Athabasca_University\/Chemistry_350:_Organic_Chemistry_I\/Chapter_3:_Organic_Compounds:_Alkanes_and_Their_Stereochemistry\/3.4_Naming_Alkanes##fixme\" 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\r\n\r\n<\/div>\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 scope=\"col\"><strong>Name<\/strong><\/th>\r\n<th scope=\"col\"><strong>Molecular\r\nFormula<\/strong><\/th>\r\n<th scope=\"col\"><strong>Structural\r\nFormula<\/strong><\/th>\r\n<th scope=\"col\"><strong>Isomers<\/strong><\/th>\r\n<th scope=\"col\"><\/th>\r\n<th scope=\"col\"><strong>Name<\/strong><\/th>\r\n<th scope=\"col\"><strong>Molecular\r\nFormula<\/strong><\/th>\r\n<th scope=\"col\"><strong>Structural\r\nFormula<\/strong><\/th>\r\n<th scope=\"col\"><strong>Isomers<\/strong><\/th>\r\n<\/tr>\r\n<\/thead>\r\n<tbody>\r\n<tr align=\"center\">\r\n<td>meth<strong>ane<\/strong><\/td>\r\n<td>CH<sub>4<\/sub><\/td>\r\n<td>CH<sub>4<\/sub><\/td>\r\n<td>1<\/td>\r\n<td><\/td>\r\n<td>hex<strong>ane<\/strong><\/td>\r\n<td>C<sub>6<\/sub>H<sub>14<\/sub><\/td>\r\n<td>CH<sub>3<\/sub>(CH<sub>2<\/sub>)<sub>4<\/sub>CH<sub>3<\/sub><\/td>\r\n<td>5<\/td>\r\n<\/tr>\r\n<tr align=\"center\">\r\n<td>eth<strong>ane<\/strong><\/td>\r\n<td>C<sub>2<\/sub>H<sub>6<\/sub><\/td>\r\n<td>CH<sub>3<\/sub>CH<sub>3<\/sub><\/td>\r\n<td>1<\/td>\r\n<td><\/td>\r\n<td>hept<strong>ane<\/strong><\/td>\r\n<td>C<sub>7<\/sub>H<sub>16<\/sub><\/td>\r\n<td>CH<sub>3<\/sub>(CH<sub>2<\/sub>)<sub>5<\/sub>CH<sub>3<\/sub><\/td>\r\n<td>9<\/td>\r\n<\/tr>\r\n<tr align=\"center\">\r\n<td>prop<strong>ane<\/strong><\/td>\r\n<td>C<sub>3<\/sub>H<sub>8<\/sub><\/td>\r\n<td>CH<sub>3<\/sub>CH<sub>2<\/sub>CH<sub>3<\/sub><\/td>\r\n<td>1<\/td>\r\n<td><\/td>\r\n<td>oct<strong>ane<\/strong><\/td>\r\n<td>C<sub>8<\/sub>H<sub>18<\/sub><\/td>\r\n<td>CH<sub>3<\/sub>(CH<sub>2<\/sub>)<sub>6<\/sub>CH<sub>3<\/sub><\/td>\r\n<td>18<\/td>\r\n<\/tr>\r\n<tr align=\"center\">\r\n<td>but<strong>ane<\/strong><\/td>\r\n<td>C<sub>4<\/sub>H<sub>10<\/sub><\/td>\r\n<td>CH<sub>3<\/sub>CH<sub>2<\/sub>CH<sub>2<\/sub>CH<sub>3<\/sub><\/td>\r\n<td>2<\/td>\r\n<td><\/td>\r\n<td>non<strong>ane<\/strong><\/td>\r\n<td>C<sub>9<\/sub>H<sub>20<\/sub><\/td>\r\n<td>CH<sub>3<\/sub>(CH<sub>2<\/sub>)<sub>7<\/sub>CH<sub>3<\/sub><\/td>\r\n<td>35<\/td>\r\n<\/tr>\r\n<tr align=\"center\">\r\n<td>pent<strong>ane<\/strong><\/td>\r\n<td>C<sub>5<\/sub>H<sub>12<\/sub><\/td>\r\n<td>CH<sub>3<\/sub>(CH<sub>2<\/sub>)<sub>3<\/sub>CH<sub>3<\/sub><\/td>\r\n<td>3<\/td>\r\n<td><\/td>\r\n<td>dec<strong>ane<\/strong><\/td>\r\n<td>C<sub>10<\/sub>H<sub>22<\/sub><\/td>\r\n<td>CH<sub>3<\/sub>(CH<sub>2<\/sub>)<sub>8<\/sub>CH<sub>3<\/sub><\/td>\r\n<td>75<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<div id=\"section_1\">\r\n\r\n\r\n<h4 class=\"editable\">Some important behavior trends and terminologies<\/h4>\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. 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\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 <strong>E<\/strong>):\r\n<p style=\"text-align: center\"><img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04211037\/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?\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<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 style=\"background-color: #ccffcc\" scope=\"row\"><strong>Group<\/strong><\/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<sub>\u00a0<\/sub><\/td>\r\n<\/tr>\r\n<tr align=\"center\" valign=\"middle\">\r\n<th style=\"background-color: #ccffcc\" scope=\"row\"><strong>Name<\/strong><\/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\nHalogen substituents are easily accommodated, using the names: fluoro (F-), chloro (Cl-), bromo (Br-) and iodo (I-).\r\n<div>\r\n<div class=\"textbox\">\r\n<p class=\"boxtitle mt-align-left\">IUPAC Rules for Alkane Nomenclature<\/p>\r\n\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\n<\/div>\r\n\r\n\r\n<\/div>\r\n<div>\r\n<div id=\"example\">\r\n<div class=\"textbox examples\">\r\n<h3>Example<\/h3>\r\n<p class=\"boxtitle\">Example 1: Halogen Substitution<\/p>\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[reveal-answer q=\"796616\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"796616\"]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[\/hidden-answer]\r\n\r\n<\/div>\r\n\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_2\">\r\n<h3 class=\"editable\">Alkyl Groups<\/h3>\r\n<p class=\"paragraph\"><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.<\/p>\r\n<p class=\"paragraph\"><img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04211039\/NamingAlkanes-Alkyl.gif\" alt=\"NamingAlkanes-Alkyl.gif\" width=\"260px\" height=\"104px\" \/><\/p>\r\n<p class=\"paragraph\">The same concept can be applied to any of the straight chain alkane names provided in the table above.<\/p>\r\n\r\n<table class=\"wiki-table mt-responsive-table\" style=\"margin: auto;border-spacing: 1px;width: 460px\" cellpadding=\"1\"><caption><em><strong>Table 3<\/strong>: Alkyl Groups Names<\/em><\/caption>\r\n<thead>\r\n<tr>\r\n<th style=\"width: 86px\" scope=\"col\"><strong>Name<\/strong><\/th>\r\n<th style=\"width: 129.5px\" scope=\"col\"><strong>Molecular Formula<\/strong><\/th>\r\n<th style=\"width: 211.5px\" scope=\"col\"><strong>Condensed Structural Formula<\/strong><\/th>\r\n<\/tr>\r\n<\/thead>\r\n<tbody>\r\n<tr class=\"table-odd\">\r\n<td style=\"width: 86px\">Methane<\/td>\r\n<td style=\"width: 129.5px\">CH<sub class=\"subscript\">4<\/sub><\/td>\r\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">4<\/sub><\/td>\r\n<\/tr>\r\n<tr class=\"table-even\">\r\n<td style=\"width: 86px\">Ethane<\/td>\r\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">2<\/sub>H<sub class=\"subscript\">6<\/sub><\/td>\r\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\r\n<\/tr>\r\n<tr class=\"table-odd\">\r\n<td style=\"width: 86px\">Propane<\/td>\r\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">3<\/sub>H<sub class=\"subscript\">8<\/sub><\/td>\r\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>CH<sub class=\"subscript\">2<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\r\n<\/tr>\r\n<tr class=\"table-even\">\r\n<td style=\"width: 86px\">Butane<\/td>\r\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">4<\/sub>H<sub class=\"subscript\">10<\/sub><\/td>\r\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>(CH<sub class=\"subscript\">2<\/sub>)<sub class=\"subscript\">2<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\r\n<\/tr>\r\n<tr class=\"table-odd\">\r\n<td style=\"width: 86px\">Pentane<\/td>\r\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">5<\/sub>H<sub class=\"subscript\">12<\/sub><\/td>\r\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>(CH<sub class=\"subscript\">2<\/sub>)<sub class=\"subscript\">3<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\r\n<\/tr>\r\n<tr class=\"table-even\">\r\n<td style=\"width: 86px\">Hexane<\/td>\r\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">6<\/sub>H<sub class=\"subscript\">14<\/sub><\/td>\r\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>(CH<sub class=\"subscript\">2<\/sub>)<sub class=\"subscript\">4<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\r\n<\/tr>\r\n<tr class=\"table-odd\">\r\n<td style=\"width: 86px\">Heptane<\/td>\r\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">7<\/sub>H<sub class=\"subscript\">16<\/sub><\/td>\r\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>(CH<sub class=\"subscript\">2<\/sub>)<sub class=\"subscript\">5<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\r\n<\/tr>\r\n<tr class=\"table-even\">\r\n<td style=\"width: 86px\">Octane<\/td>\r\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">8<\/sub>H<sub class=\"subscript\">18<\/sub><\/td>\r\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>(CH<sub class=\"subscript\">2<\/sub>)<sub class=\"subscript\">6<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\r\n<\/tr>\r\n<tr class=\"table-odd\">\r\n<td style=\"width: 86px\">Nonane<\/td>\r\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">9<\/sub>H<sub class=\"subscript\">20<\/sub><\/td>\r\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>(CH<sub class=\"subscript\">2<\/sub>)<sub class=\"subscript\">7<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\r\n<\/tr>\r\n<tr class=\"table-even\">\r\n<td style=\"width: 86px\">Decane<\/td>\r\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">10<\/sub>H<sub class=\"subscript\">22<\/sub><\/td>\r\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>(CH<sub class=\"subscript\">2<\/sub>)<sub class=\"subscript\">8<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\r\n<\/tr>\r\n<tr class=\"table-odd\">\r\n<td style=\"width: 86px\">Undecane<\/td>\r\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">11<\/sub>H<sub class=\"subscript\">24<\/sub><\/td>\r\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>(CH<sub class=\"subscript\">2<\/sub>)<sub class=\"subscript\">9<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\r\n<\/tr>\r\n<tr class=\"table-even\">\r\n<td style=\"width: 86px\">Dodecane<\/td>\r\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">12<\/sub>H<sub class=\"subscript\">26<\/sub><\/td>\r\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>(CH<sub class=\"subscript\">2<\/sub>)<sub class=\"subscript\">10<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\r\n<\/tr>\r\n<tr class=\"table-odd\">\r\n<td style=\"width: 86px\">Tridecane<\/td>\r\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">13<\/sub>H<sub class=\"subscript\">28<\/sub><\/td>\r\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>(CH<sub class=\"subscript\">2<\/sub>)<sub class=\"subscript\">11<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\r\n<\/tr>\r\n<tr class=\"table-even\">\r\n<td style=\"width: 86px\">Tetradecane<\/td>\r\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">14<\/sub>H<sub class=\"subscript\">30<\/sub><\/td>\r\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>(CH<sub class=\"subscript\">2<\/sub>)<sub class=\"subscript\">12<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\r\n<\/tr>\r\n<tr class=\"table-odd\">\r\n<td style=\"width: 86px\">Pentadecane<\/td>\r\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">15<\/sub>H<sub class=\"subscript\">32<\/sub><\/td>\r\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>(CH<sub class=\"subscript\">2<\/sub>)<sub class=\"subscript\">13<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\r\n<\/tr>\r\n<tr class=\"table-even\">\r\n<td style=\"width: 86px\">Hexadecane<\/td>\r\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">16<\/sub>H<sub class=\"subscript\">34<\/sub><\/td>\r\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>(CH<sub class=\"subscript\">2<\/sub>)<sub class=\"subscript\">14<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\r\n<\/tr>\r\n<tr class=\"table-odd\">\r\n<td style=\"width: 86px\">Heptadecane<\/td>\r\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">17<\/sub>H<sub class=\"subscript\">36<\/sub><\/td>\r\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>(CH<sub class=\"subscript\">2<\/sub>)<sub class=\"subscript\">15<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\r\n<\/tr>\r\n<tr class=\"table-even\">\r\n<td style=\"width: 86px\">Octadecane<\/td>\r\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">18<\/sub>H<sub class=\"subscript\">38<\/sub><\/td>\r\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>(CH<sub class=\"subscript\">2<\/sub>)<sub class=\"subscript\">16<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\r\n<\/tr>\r\n<tr class=\"table-odd\">\r\n<td style=\"width: 86px\">Nonadecane<\/td>\r\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">19<\/sub>H<sub class=\"subscript\">40<\/sub><\/td>\r\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>(CH<sub class=\"subscript\">2<\/sub>)<sub class=\"subscript\">17<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\r\n<\/tr>\r\n<tr class=\"table-even\">\r\n<td style=\"width: 86px\">Eicosane<\/td>\r\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">20<\/sub>H<sub class=\"subscript\">42<\/sub><\/td>\r\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>(CH<sub class=\"subscript\">2<\/sub>)<sub class=\"subscript\">18<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<div>\r\n<div id=\"section_3\">\r\n\r\n\r\n<h3 class=\"editable\">Three Rules of Naming Alkanes<\/h3>\r\n<ol>\r\n \t<li>Choose the longest, most substituted carbon chain containing a functional group.<\/li>\r\n \t<li>A carbon bonded to a functional group must have the lowest possible carbon number. If there are no functional groups, then any substitute present must have the lowest possible number.<\/li>\r\n \t<li>Take the alphabetical order into consideration; that is, after applying the first two rules given above, make sure that your substitutes and\/or functional groups are written in alphabetical order.<\/li>\r\n<\/ol>\r\n<div>\r\n<div class=\"textbox examples\">\r\n<h3>Examples<\/h3>\r\n<p class=\"boxtitle\">Example 2<\/p>\r\n<p class=\"paragraph\">What is the name of the follow molecule?<\/p>\r\n<p class=\"paragraph\"><img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04211040\/NamingAlkanes-Numbering_01.gif\" alt=\"NamingAlkanes-Numbering 01.gif\" width=\"257\" height=\"114\" \/><\/p>\r\n<p class=\"paragraph\"><strong>SOLUTION<\/strong><\/p>\r\n<p class=\"paragraph\"><strong class=\"bold\">Rule #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 aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04211042\/NamingAlkanes-Numbering_02.gif\" alt=\"NamingAlkanes-Numbering 02.gif\" width=\"301px\" height=\"134px\" \/><\/p>\r\n<p class=\"paragraph\"><strong class=\"bold\">Rule #2:<\/strong> Carbons bonded to a functional group must have the lowest possible carbon number. If there are no functional groups, then any substitute 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 substitutes 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 aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04211044\/NamingAlkanes-Numbering_03.gif\" alt=\"NamingAlkanes-Numbering 03.GIF\" width=\"311px\" height=\"134px\" \/><\/p>\r\n<p class=\"paragraph\"><strong>Rule 3<\/strong>: In this example, there is no need to utilize the third rule.\u00a0Because the two substitutes 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\r\n<\/div>\r\n<\/div>\r\n<div>\r\n<div class=\"textbox examples\">\r\n<h3>Examples<\/h3>\r\n<div>\r\n<div>\r\n<div>\r\n<p class=\"boxtitle\">Example 3:<\/p>\r\n<p class=\"paragraph\">What is the name of the follow molecule?<\/p>\r\n<p class=\"paragraph\"><img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04211046\/NamingAlkanes-Numbering_08DSL.gif\" alt=\"\" width=\"269px\" height=\"119px\" \/><\/p>\r\n<p class=\"paragraph\"><strong>SOLUTION<\/strong><\/p>\r\n<p class=\"paragraph\"><strong class=\"bold\">Rule #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 aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04211048\/NamingAlkanes-Numbering_05.gif\" alt=\"NamingAlkanes-Numbering 05.GIF\" width=\"269px\" height=\"108px\" \/><\/p>\r\n<p class=\"paragraph\"><strong class=\"bold\">Rule #2:<\/strong> Carbons bonded to a functional group must have the lowest possible carbon number. If there are no functional groups, then any substitute 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 aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04211050\/NamingAlkanes-Numbering_06.gif\" alt=\"NamingAlkanes-Numbering 06.GIF\" width=\"608px\" height=\"108px\" \/><\/p>\r\n<p class=\"paragraph\"><strong class=\"bold\">Rule #3:<\/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 aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04211052\/NamingAlkanes-Numbering_07.gif\" alt=\"NamingAlkanes-Numbering 07.GIF\" width=\"269px\" height=\"108px\" \/><\/p>\r\n<p class=\"paragraph\">The name of this molecule is thus: <strong>2-chloro,6-bromoheptane<\/strong><\/p>\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div class=\"textbox examples\">\r\n<h3>Examples<\/h3>\r\n<div>\r\n<p class=\"boxtitle\">Example 4:<\/p>\r\n\r\n<\/div>\r\n<div>\r\n<p class=\"paragraph\">What is the name of the follow molecule?<\/p>\r\n<p class=\"paragraph\"><img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04211053\/NamingAlkanes-Numbering_08.gif\" alt=\"NamingAlkanes-Numbering 08.GIF\" width=\"269px\" height=\"119px\" \/><\/p>\r\n<p class=\"paragraph\"><strong>SOLUTION<\/strong><\/p>\r\n<p class=\"paragraph\"><strong class=\"bold\">Rule #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 aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04211055\/NamingAlkanes-Numbering_09.gif\" alt=\"NamingAlkanes-Numbering 09.GIF\" width=\"269px\" height=\"119px\" \/><\/p>\r\n<p class=\"paragraph\"><strong class=\"bold\">Rule #2:<\/strong> Carbons bonded to a functional group must have the lowest possible carbon number. After taking functional groups into consideration, any substitutes 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 substitute. Therefore, the first of the two carbon chains shown below is correct.<\/p>\r\n<p class=\"paragraph\"><img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04211057\/NamingAlkanes-Numbering_10.gif\" alt=\"NamingAlkanes-Numbering 10.GIF\" width=\"269px\" height=\"243px\" \/><\/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 aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04211059\/NamingAlkanes-Naming_01.gif\" alt=\"NamingAlkanes-Naming 01.GIF\" width=\"269px\" height=\"108px\" \/><\/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\">Rule #3:<\/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\">The name of this molecule is thus:\u00a0<strong>6-bromo-2-chloro-3-methylheptane<\/strong><\/p>\r\n\r\n<\/div>\r\n<\/div>\r\n\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_4\">\r\n<div class=\"textbox exercises\">\r\n<h3>Exercises<\/h3>\r\n\r\n<div id=\"section_4\">\r\n<div id=\"s61690\">\r\n<div id=\"section_14\">\r\n<div id=\"section_15\">\r\n<h3 id=\"Questions-61690\">Questions<\/h3>\r\n<b>1.<\/b>\r\n\r\n<span><span>Are the following structures properly named, and if they are not, what is the correct naming?<\/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\/1518\/2017\/10\/04211101\/3.4.png\" alt=\"\" width=\"457\" height=\"172\" \/>\r\n\r\n<strong>2.<\/strong>\r\n\r\n<span><span>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\/1518\/2017\/10\/04211104\/3.42.png\" alt=\"\" width=\"455\" height=\"279\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_16\">\r\n\r\n\r\n<h3 id=\"Solutions-61690\">Solutions<\/h3>\r\n[reveal-answer q=\"320582\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"320582\"]\r\n\r\n1. They are both labeled incorrectly:\r\n\r\n3-bromo-2-hydroxypentane\r\n\r\n2, 3-dimethylpentane\r\n\r\n2.\r\n\r\n1 = 3,4-Dimethyl hexane\r\n\r\n2 = 2-methyl pentane\r\n\r\n3 = 2,2,4-trimethyl pentane[\/hidden-answer]\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n\r\n\r\n<\/div>\r\n<div id=\"section_5\">\r\n<h3 class=\"editable\">Contributors<\/h3>\r\n<ul>\r\n \t<li><a class=\"external\" title=\"http:\/\/science.athabascau.ca\/staff-pages\/dietmark\" href=\"http:\/\/science.athabascau.ca\/staff-pages\/dietmark\" target=\"_blank\" rel=\"external nofollow noopener\">Dr. Dietmar Kennepohl<\/a> FCIC (Professor of Chemistry, <a class=\"external\" title=\"http:\/\/www.athabascau.ca\/\" href=\"http:\/\/www.athabascau.ca\/\" target=\"_blank\" rel=\"external nofollow noopener\">Athabasca University<\/a>)<\/li>\r\n \t<li>Prof. Steven Farmer (<a class=\"external\" title=\"http:\/\/www.sonoma.edu\" href=\"http:\/\/www.sonoma.edu\" target=\"_blank\" rel=\"external nofollow noopener\">Sonoma State University<\/a>)<\/li>\r\n \t<li><a title=\"Organic_Chemistry_With_a_Biological_Emphasis\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry_Textbook_Maps\/Map%3A_Organic_Chemistry_with_a_Biological_Emphasis_(Soderberg)\" rel=\"internal\">Organic Chemistry With a Biological Emphasis <\/a>by\u00a0<a class=\"external\" title=\"http:\/\/facultypages.morris.umn.edu\/~soderbt\/\" href=\"http:\/\/facultypages.morris.umn.edu\/%7Esoderbt\/\" target=\"_blank\" rel=\"external nofollow noopener\">Tim Soderberg<\/a>\u00a0(University of Minnesota, Morris)<\/li>\r\n<\/ul>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>","rendered":"<div class=\"elm-header\">\n<div class=\"elm-header-custom\">\n<div class=\"textbox learning-objectives\">\n<h3>Objectives<\/h3>\n<div id=\"elm-main-content\" class=\"elm-content-container\">\n<div>\n<div id=\"skills\">\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>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"elm-main-content\" class=\"elm-content-container\">\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 id=\"note\">\n<div class=\"textbox\">\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><img decoding=\"async\" src=\"https:\/\/chem.libretexts.org\/LibreTexts\/Athabasca_University\/Chemistry_350%3A_Organic_Chemistry_I\/Chapter_3%3A_Organic_Compounds%3A_Alkanes_and_Their_Stereochemistry\/\/LibreTexts\/Athabasca_University\/Chemistry_350:_Organic_Chemistry_I\/Chapter_3:_Organic_Compounds:_Alkanes_and_Their_Stereochemistry\/3.4_Naming_Alkanes##fixme\" 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<\/div>\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 scope=\"col\"><strong>Name<\/strong><\/th>\n<th scope=\"col\"><strong>Molecular<br \/>\nFormula<\/strong><\/th>\n<th scope=\"col\"><strong>Structural<br \/>\nFormula<\/strong><\/th>\n<th scope=\"col\"><strong>Isomers<\/strong><\/th>\n<th scope=\"col\"><\/th>\n<th scope=\"col\"><strong>Name<\/strong><\/th>\n<th scope=\"col\"><strong>Molecular<br \/>\nFormula<\/strong><\/th>\n<th scope=\"col\"><strong>Structural<br \/>\nFormula<\/strong><\/th>\n<th scope=\"col\"><strong>Isomers<\/strong><\/th>\n<\/tr>\n<\/thead>\n<tbody>\n<tr align=\"center\">\n<td>meth<strong>ane<\/strong><\/td>\n<td>CH<sub>4<\/sub><\/td>\n<td>CH<sub>4<\/sub><\/td>\n<td>1<\/td>\n<td><\/td>\n<td>hex<strong>ane<\/strong><\/td>\n<td>C<sub>6<\/sub>H<sub>14<\/sub><\/td>\n<td>CH<sub>3<\/sub>(CH<sub>2<\/sub>)<sub>4<\/sub>CH<sub>3<\/sub><\/td>\n<td>5<\/td>\n<\/tr>\n<tr align=\"center\">\n<td>eth<strong>ane<\/strong><\/td>\n<td>C<sub>2<\/sub>H<sub>6<\/sub><\/td>\n<td>CH<sub>3<\/sub>CH<sub>3<\/sub><\/td>\n<td>1<\/td>\n<td><\/td>\n<td>hept<strong>ane<\/strong><\/td>\n<td>C<sub>7<\/sub>H<sub>16<\/sub><\/td>\n<td>CH<sub>3<\/sub>(CH<sub>2<\/sub>)<sub>5<\/sub>CH<sub>3<\/sub><\/td>\n<td>9<\/td>\n<\/tr>\n<tr align=\"center\">\n<td>prop<strong>ane<\/strong><\/td>\n<td>C<sub>3<\/sub>H<sub>8<\/sub><\/td>\n<td>CH<sub>3<\/sub>CH<sub>2<\/sub>CH<sub>3<\/sub><\/td>\n<td>1<\/td>\n<td><\/td>\n<td>oct<strong>ane<\/strong><\/td>\n<td>C<sub>8<\/sub>H<sub>18<\/sub><\/td>\n<td>CH<sub>3<\/sub>(CH<sub>2<\/sub>)<sub>6<\/sub>CH<sub>3<\/sub><\/td>\n<td>18<\/td>\n<\/tr>\n<tr align=\"center\">\n<td>but<strong>ane<\/strong><\/td>\n<td>C<sub>4<\/sub>H<sub>10<\/sub><\/td>\n<td>CH<sub>3<\/sub>CH<sub>2<\/sub>CH<sub>2<\/sub>CH<sub>3<\/sub><\/td>\n<td>2<\/td>\n<td><\/td>\n<td>non<strong>ane<\/strong><\/td>\n<td>C<sub>9<\/sub>H<sub>20<\/sub><\/td>\n<td>CH<sub>3<\/sub>(CH<sub>2<\/sub>)<sub>7<\/sub>CH<sub>3<\/sub><\/td>\n<td>35<\/td>\n<\/tr>\n<tr align=\"center\">\n<td>pent<strong>ane<\/strong><\/td>\n<td>C<sub>5<\/sub>H<sub>12<\/sub><\/td>\n<td>CH<sub>3<\/sub>(CH<sub>2<\/sub>)<sub>3<\/sub>CH<sub>3<\/sub><\/td>\n<td>3<\/td>\n<td><\/td>\n<td>dec<strong>ane<\/strong><\/td>\n<td>C<sub>10<\/sub>H<sub>22<\/sub><\/td>\n<td>CH<sub>3<\/sub>(CH<sub>2<\/sub>)<sub>8<\/sub>CH<sub>3<\/sub><\/td>\n<td>75<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<div id=\"section_1\">\n<h4 class=\"editable\">Some important behavior trends and terminologies<\/h4>\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. 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<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 <strong>E<\/strong>):<\/p>\n<p style=\"text-align: center\"><img decoding=\"async\" class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04211037\/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?<\/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<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 style=\"background-color: #ccffcc\" scope=\"row\"><strong>Group<\/strong><\/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<sub>\u00a0<\/sub><\/td>\n<\/tr>\n<tr align=\"center\" valign=\"middle\">\n<th style=\"background-color: #ccffcc\" scope=\"row\"><strong>Name<\/strong><\/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>Halogen substituents are easily accommodated, using the names: fluoro (F-), chloro (Cl-), bromo (Br-) and iodo (I-).<\/p>\n<div>\n<div class=\"textbox\">\n<p class=\"boxtitle mt-align-left\">IUPAC Rules for Alkane Nomenclature<\/p>\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<\/div>\n<\/div>\n<div>\n<div id=\"example\">\n<div class=\"textbox examples\">\n<h3>Example<\/h3>\n<p class=\"boxtitle\">Example 1: Halogen Substitution<\/p>\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 class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q796616\">Show Answer<\/span><\/p>\n<div id=\"q796616\" class=\"hidden-answer\" style=\"display: none\">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<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_2\">\n<h3 class=\"editable\">Alkyl Groups<\/h3>\n<p class=\"paragraph\"><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.<\/p>\n<p class=\"paragraph\"><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04211039\/NamingAlkanes-Alkyl.gif\" alt=\"NamingAlkanes-Alkyl.gif\" width=\"260px\" height=\"104px\" \/><\/p>\n<p class=\"paragraph\">The same concept can be applied to any of the straight chain alkane names provided in the table above.<\/p>\n<table class=\"wiki-table mt-responsive-table\" style=\"margin: auto;border-spacing: 1px;width: 460px\" cellpadding=\"1\">\n<caption><em><strong>Table 3<\/strong>: Alkyl Groups Names<\/em><\/caption>\n<thead>\n<tr>\n<th style=\"width: 86px\" scope=\"col\"><strong>Name<\/strong><\/th>\n<th style=\"width: 129.5px\" scope=\"col\"><strong>Molecular Formula<\/strong><\/th>\n<th style=\"width: 211.5px\" scope=\"col\"><strong>Condensed Structural Formula<\/strong><\/th>\n<\/tr>\n<\/thead>\n<tbody>\n<tr class=\"table-odd\">\n<td style=\"width: 86px\">Methane<\/td>\n<td style=\"width: 129.5px\">CH<sub class=\"subscript\">4<\/sub><\/td>\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">4<\/sub><\/td>\n<\/tr>\n<tr class=\"table-even\">\n<td style=\"width: 86px\">Ethane<\/td>\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">2<\/sub>H<sub class=\"subscript\">6<\/sub><\/td>\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\n<\/tr>\n<tr class=\"table-odd\">\n<td style=\"width: 86px\">Propane<\/td>\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">3<\/sub>H<sub class=\"subscript\">8<\/sub><\/td>\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>CH<sub class=\"subscript\">2<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\n<\/tr>\n<tr class=\"table-even\">\n<td style=\"width: 86px\">Butane<\/td>\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">4<\/sub>H<sub class=\"subscript\">10<\/sub><\/td>\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>(CH<sub class=\"subscript\">2<\/sub>)<sub class=\"subscript\">2<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\n<\/tr>\n<tr class=\"table-odd\">\n<td style=\"width: 86px\">Pentane<\/td>\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">5<\/sub>H<sub class=\"subscript\">12<\/sub><\/td>\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>(CH<sub class=\"subscript\">2<\/sub>)<sub class=\"subscript\">3<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\n<\/tr>\n<tr class=\"table-even\">\n<td style=\"width: 86px\">Hexane<\/td>\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">6<\/sub>H<sub class=\"subscript\">14<\/sub><\/td>\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>(CH<sub class=\"subscript\">2<\/sub>)<sub class=\"subscript\">4<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\n<\/tr>\n<tr class=\"table-odd\">\n<td style=\"width: 86px\">Heptane<\/td>\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">7<\/sub>H<sub class=\"subscript\">16<\/sub><\/td>\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>(CH<sub class=\"subscript\">2<\/sub>)<sub class=\"subscript\">5<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\n<\/tr>\n<tr class=\"table-even\">\n<td style=\"width: 86px\">Octane<\/td>\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">8<\/sub>H<sub class=\"subscript\">18<\/sub><\/td>\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>(CH<sub class=\"subscript\">2<\/sub>)<sub class=\"subscript\">6<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\n<\/tr>\n<tr class=\"table-odd\">\n<td style=\"width: 86px\">Nonane<\/td>\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">9<\/sub>H<sub class=\"subscript\">20<\/sub><\/td>\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>(CH<sub class=\"subscript\">2<\/sub>)<sub class=\"subscript\">7<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\n<\/tr>\n<tr class=\"table-even\">\n<td style=\"width: 86px\">Decane<\/td>\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">10<\/sub>H<sub class=\"subscript\">22<\/sub><\/td>\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>(CH<sub class=\"subscript\">2<\/sub>)<sub class=\"subscript\">8<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\n<\/tr>\n<tr class=\"table-odd\">\n<td style=\"width: 86px\">Undecane<\/td>\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">11<\/sub>H<sub class=\"subscript\">24<\/sub><\/td>\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>(CH<sub class=\"subscript\">2<\/sub>)<sub class=\"subscript\">9<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\n<\/tr>\n<tr class=\"table-even\">\n<td style=\"width: 86px\">Dodecane<\/td>\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">12<\/sub>H<sub class=\"subscript\">26<\/sub><\/td>\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>(CH<sub class=\"subscript\">2<\/sub>)<sub class=\"subscript\">10<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\n<\/tr>\n<tr class=\"table-odd\">\n<td style=\"width: 86px\">Tridecane<\/td>\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">13<\/sub>H<sub class=\"subscript\">28<\/sub><\/td>\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>(CH<sub class=\"subscript\">2<\/sub>)<sub class=\"subscript\">11<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\n<\/tr>\n<tr class=\"table-even\">\n<td style=\"width: 86px\">Tetradecane<\/td>\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">14<\/sub>H<sub class=\"subscript\">30<\/sub><\/td>\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>(CH<sub class=\"subscript\">2<\/sub>)<sub class=\"subscript\">12<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\n<\/tr>\n<tr class=\"table-odd\">\n<td style=\"width: 86px\">Pentadecane<\/td>\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">15<\/sub>H<sub class=\"subscript\">32<\/sub><\/td>\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>(CH<sub class=\"subscript\">2<\/sub>)<sub class=\"subscript\">13<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\n<\/tr>\n<tr class=\"table-even\">\n<td style=\"width: 86px\">Hexadecane<\/td>\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">16<\/sub>H<sub class=\"subscript\">34<\/sub><\/td>\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>(CH<sub class=\"subscript\">2<\/sub>)<sub class=\"subscript\">14<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\n<\/tr>\n<tr class=\"table-odd\">\n<td style=\"width: 86px\">Heptadecane<\/td>\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">17<\/sub>H<sub class=\"subscript\">36<\/sub><\/td>\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>(CH<sub class=\"subscript\">2<\/sub>)<sub class=\"subscript\">15<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\n<\/tr>\n<tr class=\"table-even\">\n<td style=\"width: 86px\">Octadecane<\/td>\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">18<\/sub>H<sub class=\"subscript\">38<\/sub><\/td>\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>(CH<sub class=\"subscript\">2<\/sub>)<sub class=\"subscript\">16<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\n<\/tr>\n<tr class=\"table-odd\">\n<td style=\"width: 86px\">Nonadecane<\/td>\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">19<\/sub>H<sub class=\"subscript\">40<\/sub><\/td>\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>(CH<sub class=\"subscript\">2<\/sub>)<sub class=\"subscript\">17<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\n<\/tr>\n<tr class=\"table-even\">\n<td style=\"width: 86px\">Eicosane<\/td>\n<td style=\"width: 129.5px\">C<sub class=\"subscript\">20<\/sub>H<sub class=\"subscript\">42<\/sub><\/td>\n<td style=\"width: 211.5px\">CH<sub class=\"subscript\">3<\/sub>(CH<sub class=\"subscript\">2<\/sub>)<sub class=\"subscript\">18<\/sub>CH<sub class=\"subscript\">3<\/sub><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<div>\n<div id=\"section_3\">\n<h3 class=\"editable\">Three Rules of Naming Alkanes<\/h3>\n<ol>\n<li>Choose the longest, most substituted carbon chain containing a functional group.<\/li>\n<li>A carbon bonded to a functional group must have the lowest possible carbon number. If there are no functional groups, then any substitute present must have the lowest possible number.<\/li>\n<li>Take the alphabetical order into consideration; that is, after applying the first two rules given above, make sure that your substitutes and\/or functional groups are written in alphabetical order.<\/li>\n<\/ol>\n<div>\n<div class=\"textbox examples\">\n<h3>Examples<\/h3>\n<p class=\"boxtitle\">Example 2<\/p>\n<p class=\"paragraph\">What is the name of the follow molecule?<\/p>\n<p class=\"paragraph\"><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04211040\/NamingAlkanes-Numbering_01.gif\" alt=\"NamingAlkanes-Numbering 01.gif\" width=\"257\" height=\"114\" \/><\/p>\n<p class=\"paragraph\"><strong>SOLUTION<\/strong><\/p>\n<p class=\"paragraph\"><strong class=\"bold\">Rule #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 decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04211042\/NamingAlkanes-Numbering_02.gif\" alt=\"NamingAlkanes-Numbering 02.gif\" width=\"301px\" height=\"134px\" \/><\/p>\n<p class=\"paragraph\"><strong class=\"bold\">Rule #2:<\/strong> Carbons bonded to a functional group must have the lowest possible carbon number. If there are no functional groups, then any substitute 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 substitutes 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 decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04211044\/NamingAlkanes-Numbering_03.gif\" alt=\"NamingAlkanes-Numbering 03.GIF\" width=\"311px\" height=\"134px\" \/><\/p>\n<p class=\"paragraph\"><strong>Rule 3<\/strong>: In this example, there is no need to utilize the third rule.\u00a0Because the two substitutes 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 class=\"textbox examples\">\n<h3>Examples<\/h3>\n<div>\n<div>\n<div>\n<p class=\"boxtitle\">Example 3:<\/p>\n<p class=\"paragraph\">What is the name of the follow molecule?<\/p>\n<p class=\"paragraph\"><img decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04211046\/NamingAlkanes-Numbering_08DSL.gif\" alt=\"\" width=\"269px\" height=\"119px\" \/><\/p>\n<p class=\"paragraph\"><strong>SOLUTION<\/strong><\/p>\n<p class=\"paragraph\"><strong class=\"bold\">Rule #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 decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04211048\/NamingAlkanes-Numbering_05.gif\" alt=\"NamingAlkanes-Numbering 05.GIF\" width=\"269px\" height=\"108px\" \/><\/p>\n<p class=\"paragraph\"><strong class=\"bold\">Rule #2:<\/strong> Carbons bonded to a functional group must have the lowest possible carbon number. If there are no functional groups, then any substitute 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 decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04211050\/NamingAlkanes-Numbering_06.gif\" alt=\"NamingAlkanes-Numbering 06.GIF\" width=\"608px\" height=\"108px\" \/><\/p>\n<p class=\"paragraph\"><strong class=\"bold\">Rule #3:<\/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 decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04211052\/NamingAlkanes-Numbering_07.gif\" alt=\"NamingAlkanes-Numbering 07.GIF\" width=\"269px\" height=\"108px\" \/><\/p>\n<p class=\"paragraph\">The name of this molecule is thus: <strong>2-chloro,6-bromoheptane<\/strong><\/p>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div class=\"textbox examples\">\n<h3>Examples<\/h3>\n<div>\n<p class=\"boxtitle\">Example 4:<\/p>\n<\/div>\n<div>\n<p class=\"paragraph\">What is the name of the follow molecule?<\/p>\n<p class=\"paragraph\"><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04211053\/NamingAlkanes-Numbering_08.gif\" alt=\"NamingAlkanes-Numbering 08.GIF\" width=\"269px\" height=\"119px\" \/><\/p>\n<p class=\"paragraph\"><strong>SOLUTION<\/strong><\/p>\n<p class=\"paragraph\"><strong class=\"bold\">Rule #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 decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04211055\/NamingAlkanes-Numbering_09.gif\" alt=\"NamingAlkanes-Numbering 09.GIF\" width=\"269px\" height=\"119px\" \/><\/p>\n<p class=\"paragraph\"><strong class=\"bold\">Rule #2:<\/strong> Carbons bonded to a functional group must have the lowest possible carbon number. After taking functional groups into consideration, any substitutes 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 substitute. Therefore, the first of the two carbon chains shown below is correct.<\/p>\n<p class=\"paragraph\"><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04211057\/NamingAlkanes-Numbering_10.gif\" alt=\"NamingAlkanes-Numbering 10.GIF\" width=\"269px\" height=\"243px\" \/><\/p>\n<p class=\"paragraph\">Therefore,\u00a0the first numbering scheme is the appropriate one to use.<\/p>\n<p class=\"paragraph\"><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04211059\/NamingAlkanes-Naming_01.gif\" alt=\"NamingAlkanes-Naming 01.GIF\" width=\"269px\" height=\"108px\" \/><\/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\">Rule #3:<\/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\">The name of this molecule is thus:\u00a0<strong>6-bromo-2-chloro-3-methylheptane<\/strong><\/p>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_4\">\n<div class=\"textbox exercises\">\n<h3>Exercises<\/h3>\n<div id=\"section_4\">\n<div id=\"s61690\">\n<div id=\"section_14\">\n<div id=\"section_15\">\n<h3 id=\"Questions-61690\">Questions<\/h3>\n<p><b>1.<\/b><\/p>\n<p><span><span>Are the following structures properly named, and if they are not, what is the correct naming?<\/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\/1518\/2017\/10\/04211101\/3.4.png\" alt=\"\" width=\"457\" height=\"172\" \/><\/p>\n<p><strong>2.<\/strong><\/p>\n<p><span><span>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\/1518\/2017\/10\/04211104\/3.42.png\" alt=\"\" width=\"455\" height=\"279\" \/><\/p>\n<\/div>\n<div id=\"section_16\">\n<h3 id=\"Solutions-61690\">Solutions<\/h3>\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q320582\">Show Answer<\/span><\/p>\n<div id=\"q320582\" class=\"hidden-answer\" style=\"display: none\">\n<p>1. They are both labeled incorrectly:<\/p>\n<p>3-bromo-2-hydroxypentane<\/p>\n<p>2, 3-dimethylpentane<\/p>\n<p>2.<\/p>\n<p>1 = 3,4-Dimethyl hexane<\/p>\n<p>2 = 2-methyl pentane<\/p>\n<p>3 = 2,2,4-trimethyl pentane<\/p><\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_5\">\n<h3 class=\"editable\">Contributors<\/h3>\n<ul>\n<li><a class=\"external\" title=\"http:\/\/science.athabascau.ca\/staff-pages\/dietmark\" href=\"http:\/\/science.athabascau.ca\/staff-pages\/dietmark\" target=\"_blank\" rel=\"external nofollow noopener\">Dr. Dietmar Kennepohl<\/a> FCIC (Professor of Chemistry, <a class=\"external\" title=\"http:\/\/www.athabascau.ca\/\" href=\"http:\/\/www.athabascau.ca\/\" target=\"_blank\" rel=\"external nofollow noopener\">Athabasca University<\/a>)<\/li>\n<li>Prof. Steven Farmer (<a class=\"external\" title=\"http:\/\/www.sonoma.edu\" href=\"http:\/\/www.sonoma.edu\" target=\"_blank\" rel=\"external nofollow noopener\">Sonoma State University<\/a>)<\/li>\n<li><a title=\"Organic_Chemistry_With_a_Biological_Emphasis\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry_Textbook_Maps\/Map%3A_Organic_Chemistry_with_a_Biological_Emphasis_(Soderberg)\" rel=\"internal\">Organic Chemistry With a Biological Emphasis <\/a>by\u00a0<a class=\"external\" title=\"http:\/\/facultypages.morris.umn.edu\/~soderbt\/\" href=\"http:\/\/facultypages.morris.umn.edu\/%7Esoderbt\/\" target=\"_blank\" rel=\"external nofollow noopener\">Tim Soderberg<\/a>\u00a0(University of Minnesota, Morris)<\/li>\n<\/ul>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n","protected":false},"author":311,"menu_order":5,"template":"","meta":{"_candela_citation":"[]","CANDELA_OUTCOMES_GUID":"","pb_show_title":"on","pb_short_title":"","pb_subtitle":"","pb_authors":[],"pb_section_license":""},"chapter-type":[],"contributor":[],"license":[],"class_list":["post-669","chapter","type-chapter","status-publish","hentry"],"part":21,"_links":{"self":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/669","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters"}],"about":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/types\/chapter"}],"author":[{"embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/users\/311"}],"version-history":[{"count":5,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/669\/revisions"}],"predecessor-version":[{"id":2099,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/669\/revisions\/2099"}],"part":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/parts\/21"}],"metadata":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/669\/metadata\/"}],"wp:attachment":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/media?parent=669"}],"wp:term":[{"taxonomy":"chapter-type","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapter-type?post=669"},{"taxonomy":"contributor","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/contributor?post=669"},{"taxonomy":"license","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/license?post=669"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}