{"id":960,"date":"2017-10-19T15:03:12","date_gmt":"2017-10-19T15:03:12","guid":{"rendered":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/?post_type=chapter&#038;p=960"},"modified":"2018-10-03T19:32:10","modified_gmt":"2018-10-03T19:32:10","slug":"naming-alkenes","status":"publish","type":"chapter","link":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/chapter\/naming-alkenes\/","title":{"raw":"Naming Alkenes","rendered":"Naming Alkenes"},"content":{"raw":"<div class=\"elm-header\">\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 an acyclic or cyclic alkene, given its Kekul\u00e9, condensed or shorthand structure.<\/li>\r\n \t<li>draw the Kekul\u00e9, condensed or shorthand structure of an alkene (cyclic or acyclic), given its IUPAC name.<\/li>\r\n \t<li>give the IUPAC equivalent of the following trivial names: ethylene, propylene, isobutylene and isoprene.<\/li>\r\n \t<li>draw the structure of a vinyl (ethenyl) and allyl (2-propenyl) group, and use these names in alkene nomenclature.<\/li>\r\n<\/ol>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div class=\"textbox\">\r\n<div class=\"elm-header\"><\/div>\r\n<div id=\"elm-main-content\" class=\"elm-content-container\">\r\n<div>\r\n<div id=\"note\">\r\n<h3 class=\"boxtitle\">Study Notes<\/h3>\r\nThis course uses IUPAC nomenclature; therefore, you need not usually memorize a large number of trivial names. However, you will encounter some trivial names so frequently in books and articles that they soon become familiar.\r\n\r\nAn alkene that can exhibit geometric isomerism has not been properly named unless its name specifies whether the double bond (or bonds) is (or are) cis or trans. The most effective way of giving this information is discussed, and more details of cis and trans follow in Section 7.4.\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\nAlkenes contain carbon-carbon double bonds and are <a class=\"internal\" title=\"Wikitexts\/UCD Chem 118B\/Chem 118B Topics\/Degree of Unsaturation-Another Aid to Identifying Molecular Structure\" href=\"https:\/\/chem.libretexts.org\/Core\/Organic_Chemistry\/Alkenes\/Properties_of_Alkenes\/Degree_of_Unsaturation\" rel=\"internal\">unsaturated<\/a> hydrocarbons with the molecular formula is C<sub>n<\/sub>H<sub>2n<\/sub>. This is also the same molecular formula as <a class=\"internal mt-disabled\" title=\"Wikitexts\/UCD Chem 118A\/ChemWiki Module Topics for Chem 118B\/Structure of Organic Molecules\/Nomenclature of Cycloalkanes\" rel=\"broken\">cycloalkanes<\/a>. Alkenes are named by dropping the -ane ending of the parent and adding -ene.\r\n\r\n<\/div>\r\n<div id=\"elm-main-content\" class=\"elm-content-container\">\r\n<div id=\"section_1\">\r\n<h3 class=\"editable\">Introduction<\/h3>\r\nThe parent structure is the longest chain containing both carbon atoms of the double bond. The two carbon atoms of a double bond and the four atoms attached to them lie in a plane, with bond angles of approximately 120\u00b0 A double bond consists of one sigma bond formed by overlap of sp<sup>2<\/sup><a class=\"internal\" title=\"Physical Chemistry\/Quantum Mechanics\/The Chemical Bond\/Hybridization\" href=\"https:\/\/chem.libretexts.org\/Core\/Physical_and_Theoretical_Chemistry\/Chemical_Bonding\/Valence_Bond_Theory\/Hybridization\" rel=\"internal\"><span class=\"internal\">hybrid orbitals<\/span><\/a> and one pi bond formed by overlap of parallel 2 p orbitals\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\/05135122\/alkene7.png\" alt=\"alkene7.png\" width=\"287px\" height=\"179px\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_2\">\r\n<h3 class=\"editable\">The Basic Rules<\/h3>\r\nFor straight chain alkenes, it is the same basic rules as <a class=\"internal mt-disabled\" title=\"Organic Chemistry\/Hydrocarbons\/Alkanes\/Nomenclature of Alkanes\" rel=\"broken\">nomenclature of alkanes<\/a> except change the suffix to \"-ene.\"\r\n<ol start=\"1\">\r\n \t<li>Find the Longest Carbon Chain that Contains the Carbon Carbon double bond. If you have two ties for longest Carbon chain, and both chains contain a Carbon Carbon double bond, then identify the most substituted chain.<\/li>\r\n \t<li>Give the lowest possible number to the Carbon Carbon double bond.\r\n<ul>\r\n \t<li>Do not need to number cycloalkenes because it is understood that the double bond is in the one position.<\/li>\r\n \t<li>Alkenes that have the same molecular formula but the location of the doble bonds are different means they are constitutional isomers.<\/li>\r\n \t<li>Functional Groups with higher priority:<\/li>\r\n<\/ul>\r\n<\/li>\r\n \t<li>Add substituents and their position to the alkene as prefixes.\u00a0 Of course remember to give the lowest numbers possible. And remember to name them in alphabetical order when writting them.<\/li>\r\n \t<li>Next is identifying <a class=\"internal\" title=\"Organic Chemistry\/Chirality and Stereoisomers\" href=\"https:\/\/chem.libretexts.org\/Core\/Organic_Chemistry\/Chirality\/Chirality_and_Stereoisomers\" rel=\"internal\">stereoisomers<\/a>. when there are only two non hydrogen attachments to the alkene then use cis and trans to name the molecule.<\/li>\r\n<\/ol>\r\n<img src=\"https:\/\/chem.libretexts.org\/LibreTexts\/Athabasca_University\/Chemistry_350%3A_Organic_Chemistry_I\/Chapter_7%3A_Alkenes%3A_Structure_and_Reactivity\/denied:data:image\/png;base64,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#fixme\" alt=\"\" width=\"162\" height=\"62\" \/>\r\n\r\nIn this diagram this is a cis conformation. It has both the substituents going upward. This molecule would be called (cis) 5-chloro-3-heptene.)\r\n\r\nTrans would look like this\r\n\r\nv. On the other hand if there are 3 or 4 non-hydrogen different atoms attached to the alkene then use the E, Z system.\r\n\r\nE (entgegen) means the higher priority groups are opposite one another relative to the double bond.\r\n\r\nZ (zusammen) means the higher priority groups are on the same side relative to the double bond.\r\n\r\n(You could think of Z as Zame Zide to help memorize it.)\r\n\r\n<img src=\"https:\/\/chem.libretexts.org\/LibreTexts\/Athabasca_University\/Chemistry_350%3A_Organic_Chemistry_I\/Chapter_7%3A_Alkenes%3A_Structure_and_Reactivity\/denied:data:image\/png;base64,iVBORw0KGgoAAAANSUhEUgAAAGcAAAAoCAIAAABsLXMXAAACd0lEQVRoge2YMauyUBjH+zwNTc\/YEk5tgQRuQatni5YGwU8gRLQ6HZpqua2CQ1O4GIRruDk06CZneN7hXLrv7VpdvR5PB\/xNouLz98fRc57TwZbydGQHUJIOIjLGptOpUZ7RaDSZTGS\/AiLicrkcDocVXmEwGOz3+7LlPsdaHMdRJbbbrWVZdUsoh+d5i8WiWv7T6WSaZhiGpSrW8IV6nidR3N+rM8bKiqvnvyZLXF11y4qrbTZoXly9Fbm4w+Hwm5vrnEObFCeiFmNsPp97nvfyzppXHvxlGGP1PrawiqCHW5b1Ulz96zXP80zTFCeugRH9UpyQVW4YhoLENfYTeC5OVG8gQpzruk1OOE\/ECeyo7sRFUdQpyf+hXdd1XVdc2kIeiRPbh9Y14qQo4xSKE969\/12cRGWcn+Ka2PMIw7Df74\/H4wrddbfbXa\/XDYR8zp24hnaKzudzte56NpvJHWg3rtfr7fjd99cYY71eL8sy2UG+8e7WEPF4PJqmKTvFNxSwhoiGYURRJDvFF2pYi+NY0zTZKb5QwxoiOo6z2+1kp\/hEGWtZlmma9ibTgjLWEHG32zmOIzsFolrWEFHTtDiOZadQzVoURYZhyE6hmjVE3Gw2oveKX6KeNUQMgkDXdQAAAEJImqb8PCEkSZIGAqhnbbVaAYDv+4iYJIlt2wCQ5zkiAsDlcmkgg2LW0jQFgLs+Qdd1LrG1VgylFAAeXW2tFUMp1XX90dXWWjGttSr4vv\/zC6WUfnx8YGvtCQDAHXHyPL+daa09JAgCALBtm1LKP1hCCL\/UWntGmqaUUkKIbdt8zcGhlPKFm2iUtCad1loVWmtV+AfR7pC9\/\/GCNAAAAABJRU5ErkJggg==#fixme\" alt=\"\" width=\"166\" height=\"64\" \/>\r\n\r\nIn this example it is E-4-chloro-3-heptene. It is E because the Chlorine and the CH<sub>2<\/sub>CH<sub>3<\/sub> are the two higher priorities and they are on opposite sides.\r\n\r\nvi. A hydroxyl group gets precedence over th double bond. Therefore alkenes containing alchol groups are called alkenols. And the prefix becomes --enol. And this means that now the alcohol gets lowest priority over the alkene.\r\n\r\nvii. Lastly remember that alkene substituents are called alkenyl. Suffix --enyl.\r\n\r\nHere is a chart containing the systemic name for the first twenty straight chain alkenes.\r\n<table style=\"margin: auto;border-spacing: 1px\" border=\"1\" cellpadding=\"1\"><caption><em><strong>Table 7.3.1<\/strong>: systemic name for the first twenty straight chain alkenes.<\/em><\/caption>\r\n<tbody>\r\n<tr>\r\n<td><strong>Name<\/strong><\/td>\r\n<td><strong>Molecular formula<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>Ethene<\/td>\r\n<td>C<sub>2<\/sub>H<sub>4<\/sub><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>Propene<\/td>\r\n<td>C<sub>3<\/sub>H<sub>6<\/sub><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>Butene<\/td>\r\n<td>C<sub>4<\/sub>H<sub>8<\/sub><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>\u00a0Pentene<\/td>\r\n<td>\u00a0C<sub>5<\/sub>H<sub>10<\/sub><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>\u00a0Hexene<\/td>\r\n<td>\u00a0C<sub>6<\/sub>H<sub>12<\/sub><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>\u00a0Heptene<\/td>\r\n<td>\u00a0C<sub>7<\/sub>H<sub>14<\/sub><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>\u00a0Octene<\/td>\r\n<td>\u00a0C<sub>8<\/sub>H<sub>16<\/sub><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>\u00a0Nonene<\/td>\r\n<td>\u00a0C<sub>9<\/sub>H<sub>18<\/sub><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>\u00a0Decene<\/td>\r\n<td>\u00a0C<sub>10<\/sub>H<sub>20<\/sub><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>\u00a0Undecene<\/td>\r\n<td>\u00a0C<sub>11<\/sub>H<sub>22<\/sub><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>\u00a0Dodecene<\/td>\r\n<td>\u00a0C<sub>12<\/sub>H<sub>24<\/sub><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>\u00a0Tridecene<\/td>\r\n<td>\u00a0C<sub>13<\/sub>H<sub>26<\/sub><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>\u00a0Tetradecene<\/td>\r\n<td>\u00a0C<sub>14<\/sub>H<sub>28<\/sub><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>\u00a0Pentadecene<\/td>\r\n<td>\u00a0C<sub>15<\/sub>H<sub>30<\/sub><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>\u00a0Hexadecene<\/td>\r\n<td>\u00a0C<sub>16<\/sub>H<sub>32<\/sub><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>Heptadecene<\/td>\r\n<td>C<sub>17<\/sub>H<sub>34<\/sub><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>\u00a0Octadecene<\/td>\r\n<td>\u00a0C<sub>18<\/sub>H<sub>36<\/sub><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>\u00a0Nonadecene<\/td>\r\n<td>\u00a0C<sub>19<\/sub>H<sub>38<\/sub><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>\u00a0Eicosene<\/td>\r\n<td>\u00a0C<sub>20<\/sub>H<sub>40<\/sub><\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\nDid you notice how there is no methene? Because it is impossible for a Carbon to have a double bond with nothing.\r\n\r\n<\/div>\r\n<div id=\"section_3\">\r\n<h3 class=\"editable\">Geometric Isomers<\/h3>\r\nDouble bonds can exist as geometric isomers and these isomers are designated by using either the cis \/ trans designation or the modern E \/ Z designation.\r\n<div id=\"section_4\">\r\n<h4 class=\"editable\"><em>cis <\/em>Isomers<\/h4>\r\n.The two largest groups are on the same side of the double bond.\r\n\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135124\/alkenenomenclature9.gif\" alt=\"\" width=\"85px\" height=\"85px\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_5\">\r\n<h4 class=\"editable\"><em>trans <\/em>Isomers<\/h4>\r\n...The two largest groups are on opposite sides of the double bond.\r\n\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135124\/alkenenomenclature10.gif\" alt=\"\" width=\"85px\" height=\"85px\" \/>\r\n\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_6\">\r\n<h3 class=\"editable\">E\/Z nomenclature<\/h3>\r\nE = entgegan (\"trans\") Z = zusamen (\"cis\")\r\n\r\nPriority of groups is based on the atomic mass of attached atoms (not the size of the group). An atom attached by a multiple bond is counted once for each bond.\r\n\r\nfluorine atom &gt; isopropyl group &gt; n-hexyl group\r\n\r\ndeuterium atom &gt; hydrogen atom\r\n\r\n-CH<sub>2<\/sub>-CH=CH<sub>2<\/sub> &gt; -CH<sub>2<\/sub>CH<sub>2<\/sub>CH<sub>3<\/sub>\r\n<div class=\"textbox examples\">\r\n<h3>Example<\/h3>\r\nTry to name the following compounds using both conventions...\r\n\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135125\/alkenenomenclature11.gif\" alt=\"\" width=\"198px\" height=\"117px\" \/>\r\n\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135127\/alkenenomenclature12.gif\" alt=\"\" width=\"198px\" height=\"144px\" \/>\r\n\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_7\">\r\n<h3 class=\"editable\">Common names<\/h3>\r\nRemove the -ane suffix and add -ylene. There are a couple of unique ones like ethenyl's common name is vinyl and 2-propenyl's common name is allyl. That you should know are...\r\n<ul>\r\n \t<li>vinyl substituent H<sub>2<\/sub>C=CH-<\/li>\r\n \t<li>allyl substituent H<sub>2<\/sub>C=CH-CH<sub>2<\/sub>-<\/li>\r\n \t<li>allene molecule H<sub>2<\/sub>C=C=CH<sub>2<\/sub><\/li>\r\n \t<li>isoprene<\/li>\r\n<\/ul>\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135128\/alkenenomenclature4.gif\" alt=\"\" width=\"137px\" height=\"119px\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_8\">\r\n<h3 class=\"editable\">Endocyclic Alkenes<\/h3>\r\nEndocyclic double bonds have both carbons in the ring and exocyclic double bonds have only one carbon as part of the ring.\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\/05135129\/cycloalkane.jpg\" alt=\"cycloalkane.jpg\" width=\"332px\" height=\"247px\" \/>\r\n\r\nCyclopentene is an example of an endocyclic double bond.\r\n\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135131\/alkenenomenclature5.gif\" alt=\"\" width=\"61px\" height=\"65px\" \/>\r\n\r\nMethylenecylopentane is an example of an exocyclic double bond.\r\n\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135131\/alkenenomenclature6.gif\" alt=\"\" width=\"120px\" height=\"58px\" \/>\r\n\r\nName the following compounds...\r\n\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135132\/alkenenomenclature7.gif\" alt=\"\" width=\"91px\" height=\"78px\" \/>\r\n\r\n1-methylcyclobutene. The methyl group places the double bond. It is correct to also name this compound as 1-methylcyclobut-1-ene.\r\n\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135134\/alkenenomenclature8.gif\" alt=\"\" width=\"172px\" height=\"82px\" \/>\r\n\r\n1-ethenylcyclohexene, the methyl group places the double bond. It is correct to also name this compound as 1-ethenylcyclohex-1-ene. A common name would be 1-vinylcyclohexene.\r\n\r\nTry to draw structures for the following compounds...\r\n\r\n<a class=\"external\" href=\"http:\/\/chemistry.boisestate.edu\/richardbanks\/organic\/nomenclature\/alkenenomenclature10.htm\" target=\"_blank\" rel=\"external nofollow noopener\"><img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135135\/alkenenomenclature14.gif\" alt=\"\" width=\"222px\" height=\"93px\" \/>\u00a0 <\/a>\r\n<ul>\r\n \t<li>\u00a02-vinyl-1,3-cyclohexadiene<\/li>\r\n<\/ul>\r\n<a class=\"external\" href=\"http:\/\/chemistry.boisestate.edu\/richardbanks\/organic\/nomenclature\/alkenenomenclature11.htm\" target=\"_blank\" rel=\"external nofollow noopener\"><img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135136\/alkenenomenclature15.gif\" alt=\"\" width=\"180px\" height=\"82px\" \/>\u00a0 <\/a>\r\n\r\n<\/div>\r\n<div id=\"section_9\">\r\n<div class=\"textbox examples\">\r\n<h3>Examples<\/h3>\r\n<p style=\"text-align: center\"><img class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135138\/nomprb7.gif\" alt=\"image\" \/><\/p>\r\nBoth these compounds have double bonds, making them alkenes. In example (1) the longest chain consists of six carbons, so the root name of this compound will be hexene. Three methyl substituents (colored red) are present. Numbering the six-carbon chain begins at the end nearest the double bond (the left end), so the methyl groups are located on carbons 2 &amp; 5. The IUPAC name is therefore: 2,5,5-trimethyl-2-hexene.\r\n\r\nIn example (2) the longest chain incorporating both carbon atoms of the double bond has a length of five. There is a seven-carbon chain, but it contains only one of the double bond carbon atoms. Consequently, the root name of this compound will be pentene. There is a propyl substituent on the inside double bond carbon atom (#2), so the IUPAC name is: 2-propyl-1-pentene.\r\n<p style=\"text-align: center\"><img class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135140\/nomprb8.gif\" alt=\"image\" \/><\/p>\r\nThe double bond in example (3) is located in the center of a six-carbon chain. The double bond would therefore have a locator number of 3 regardless of the end chosen to begin numbering. The right hand end is selected because it gives the lowest first-substituent number (2 for the methyl as compared with 3 for the ethyl if numbering were started from the left). The IUPAC name is assigned as shown.\r\n\r\nExample (4) is a diene (two double bonds). Both double bonds must be contained in the longest chain, which is therefore five- rather than six-carbons in length. The second and fourth carbons of this 1,4-pentadiene are both substituted, so the numbering begins at the end nearest the alphabetically first-cited substituent (the ethyl group).\r\n<p style=\"text-align: center\"><img src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135143\/nomprb9.gif\" alt=\"image\" \/><\/p>\r\nThese examples include rings of carbon atoms as well as some carbon-carbon triple bonds. Example (6) is best named as an alkyne bearing a cyclobutyl substituent. Example (7) is simply a ten-membered ring containing both a double and a triple bond. The double bond is cited first in the IUPAC name, so numbering begins with those two carbons in the direction that gives the triple bond carbons the lowest locator numbers. Because of the linear geometry of a triple bond, a-ten membered ring is the smallest ring in which this functional group is easily accommodated. Example (8) is a cyclooctatriene (three double bonds in an eight-membered ring). The numbering must begin with one of the end carbons of the conjugated diene moiety (adjacent double bonds), because in this way the double bond carbon atoms are assigned the smallest possible locator numbers (1, 2, 3, 4, 6 &amp; 7). Of the two ways in which this can be done, we choose the one that gives the vinyl substituent the lower number.\r\n\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_10\">\r\n<h3 class=\"editable\">Outside links<\/h3>\r\n<ul>\r\n \t<li><a class=\"external\" title=\"http:\/\/www.vanderbilt.edu\/AnS\/Chemistry\/Rizzo\/chem220a\/alkenes.pdf\" href=\"http:\/\/www.vanderbilt.edu\/AnS\/Chemistry\/Rizzo\/chem220a\/alkenes.pdf\" rel=\"freeklink\">http:\/\/www.vanderbilt.edu\/AnS\/Chemis...0a\/alkenes.pdf<\/a><\/li>\r\n<\/ul>\r\n<\/div>\r\n<div id=\"section_11\">\r\n<h3 class=\"editable\">References<\/h3>\r\n<ol>\r\n \t<li>Vollhardt, Peter, and Neil E. Schore. <u>Organic\u00a0Chemistry:\u00a0Structure and Function<\/u>.\u00a05th Edition.\u00a0New York:\u00a0W.\u00a0H. Freeman &amp;\u00a0Company, 2007.<\/li>\r\n<\/ol>\r\n<\/div>\r\n<div id=\"section_12\">\r\n<div class=\"textbox examples\">\r\n<h3>Examples<\/h3>\r\n<div id=\"section_12\">\r\n<h3 class=\"editable\">Problems<\/h3>\r\n1. Try to name the following compounds...\r\n\r\n<img class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135145\/alkenenomenclature1.gif\" alt=\"image\" \/>\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\/05135147\/alkenenomenclature2.gif\" alt=\"\" width=\"322px\" height=\"87px\" \/>\r\n\r\n2. Try to draw structures for the following compounds...\r\n<ul>\r\n \t<li>\u00a02-pentene<\/li>\r\n \t<li>\u00a03-heptene<\/li>\r\n<\/ul>\r\n3. Give the double bond the lowest possible numbers regardless of substituent placement.\r\n\r\n\u2022 Try to name the following compound...\r\n\r\n<img class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135148\/alkenenomenclature3.gif\" alt=\"image\" \/>\r\n\r\n\u2022 Try to draw a structure for the following compound...\r\n\r\n4-methyl-2-pentene\r\n\r\n4. Name the following structures:\r\n\r\n<img class=\"internal left aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135150\/alkene_problem_2.jpg\" alt=\"alkene problem 2.jpg\" width=\"348px\" height=\"217px\" \/>\r\n\r\n5. Draw (Z)-5-Chloro-3-ethly-4-hexen-2-ol\r\n\r\n<\/div>\r\n<div id=\"section_13\">\r\n<h3 class=\"editable\">Answers<\/h3>\r\n<p class=\"editable\">[reveal-answer q=\"699159\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"699159\"]<\/p>\r\n1.1-pentene or pent-1-ene; 2-ethyl-1-hexene or 2-ethylhex-1-ene\r\n\r\n2. CH3\u2013CH=CH\u2013CH2\u2013CH3; CH3\u2013CH2\u2013CH=CH\u2013CH2\u2013CH2\u2013CH3\r\n\r\n3.\u00a04-methyl-1-pentene; CH3\u2013CH=CH\u2013CH(CH3)\u2013CH3\r\n\r\n4.(I) trans-8-ethyl-3-undecene; (II) E-5-bromo-4-chloro-7,7-dimethyl-4-undecene;(III) Z-1,2-difluoro-cyclohexene; (IV) 4-ethenylcyclohexanol\r\n\r\n5.\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\/05135155\/alkene9.jpg\" alt=\"alkene9.jpg\" width=\"334px\" height=\"208px\" \/>[\/hidden-answer]\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_14\">\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>S. Devarajan (UCD)<\/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<\/ul>\r\n<ul>\r\n \t<li><a class=\"external\" title=\"https:\/\/chemistry.boisestate.edu\/richardbanks\/rcb2.htm\" href=\"http:\/\/chemistry.boisestate.edu\/richardbanks\/rcb2.htm\" target=\"_blank\" rel=\"external nofollow noopener\">Richard Banks<\/a> (<a class=\"external\" title=\"https:\/\/chemistry.boisestate.edu\/\" href=\"http:\/\/chemistry.boisestate.edu\/\" target=\"_blank\" rel=\"external nofollow noopener\">Boise State University<\/a>)<\/li>\r\n<\/ul>\r\n<\/div>\r\n<\/div>","rendered":"<div class=\"elm-header\">\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 an acyclic or cyclic alkene, given its Kekul\u00e9, condensed or shorthand structure.<\/li>\n<li>draw the Kekul\u00e9, condensed or shorthand structure of an alkene (cyclic or acyclic), given its IUPAC name.<\/li>\n<li>give the IUPAC equivalent of the following trivial names: ethylene, propylene, isobutylene and isoprene.<\/li>\n<li>draw the structure of a vinyl (ethenyl) and allyl (2-propenyl) group, and use these names in alkene nomenclature.<\/li>\n<\/ol>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div class=\"textbox\">\n<div class=\"elm-header\"><\/div>\n<div id=\"elm-main-content\" class=\"elm-content-container\">\n<div>\n<div id=\"note\">\n<h3 class=\"boxtitle\">Study Notes<\/h3>\n<p>This course uses IUPAC nomenclature; therefore, you need not usually memorize a large number of trivial names. However, you will encounter some trivial names so frequently in books and articles that they soon become familiar.<\/p>\n<p>An alkene that can exhibit geometric isomerism has not been properly named unless its name specifies whether the double bond (or bonds) is (or are) cis or trans. The most effective way of giving this information is discussed, and more details of cis and trans follow in Section 7.4.<\/p>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<p>Alkenes contain carbon-carbon double bonds and are <a class=\"internal\" title=\"Wikitexts\/UCD Chem 118B\/Chem 118B Topics\/Degree of Unsaturation-Another Aid to Identifying Molecular Structure\" href=\"https:\/\/chem.libretexts.org\/Core\/Organic_Chemistry\/Alkenes\/Properties_of_Alkenes\/Degree_of_Unsaturation\" rel=\"internal\">unsaturated<\/a> hydrocarbons with the molecular formula is C<sub>n<\/sub>H<sub>2n<\/sub>. This is also the same molecular formula as <a class=\"internal mt-disabled\" title=\"Wikitexts\/UCD Chem 118A\/ChemWiki Module Topics for Chem 118B\/Structure of Organic Molecules\/Nomenclature of Cycloalkanes\" rel=\"broken\">cycloalkanes<\/a>. Alkenes are named by dropping the -ane ending of the parent and adding -ene.<\/p>\n<\/div>\n<div id=\"elm-main-content\" class=\"elm-content-container\">\n<div id=\"section_1\">\n<h3 class=\"editable\">Introduction<\/h3>\n<p>The parent structure is the longest chain containing both carbon atoms of the double bond. The two carbon atoms of a double bond and the four atoms attached to them lie in a plane, with bond angles of approximately 120\u00b0 A double bond consists of one sigma bond formed by overlap of sp<sup>2<\/sup><a class=\"internal\" title=\"Physical Chemistry\/Quantum Mechanics\/The Chemical Bond\/Hybridization\" href=\"https:\/\/chem.libretexts.org\/Core\/Physical_and_Theoretical_Chemistry\/Chemical_Bonding\/Valence_Bond_Theory\/Hybridization\" rel=\"internal\"><span class=\"internal\">hybrid orbitals<\/span><\/a> and one pi bond formed by overlap of parallel 2 p orbitals<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135122\/alkene7.png\" alt=\"alkene7.png\" width=\"287px\" height=\"179px\" \/><\/p>\n<\/div>\n<div id=\"section_2\">\n<h3 class=\"editable\">The Basic Rules<\/h3>\n<p>For straight chain alkenes, it is the same basic rules as <a class=\"internal mt-disabled\" title=\"Organic Chemistry\/Hydrocarbons\/Alkanes\/Nomenclature of Alkanes\" rel=\"broken\">nomenclature of alkanes<\/a> except change the suffix to &#8220;-ene.&#8221;<\/p>\n<ol start=\"1\">\n<li>Find the Longest Carbon Chain that Contains the Carbon Carbon double bond. If you have two ties for longest Carbon chain, and both chains contain a Carbon Carbon double bond, then identify the most substituted chain.<\/li>\n<li>Give the lowest possible number to the Carbon Carbon double bond.\n<ul>\n<li>Do not need to number cycloalkenes because it is understood that the double bond is in the one position.<\/li>\n<li>Alkenes that have the same molecular formula but the location of the doble bonds are different means they are constitutional isomers.<\/li>\n<li>Functional Groups with higher priority:<\/li>\n<\/ul>\n<\/li>\n<li>Add substituents and their position to the alkene as prefixes.\u00a0 Of course remember to give the lowest numbers possible. And remember to name them in alphabetical order when writting them.<\/li>\n<li>Next is identifying <a class=\"internal\" title=\"Organic Chemistry\/Chirality and Stereoisomers\" href=\"https:\/\/chem.libretexts.org\/Core\/Organic_Chemistry\/Chirality\/Chirality_and_Stereoisomers\" rel=\"internal\">stereoisomers<\/a>. when there are only two non hydrogen attachments to the alkene then use cis and trans to name the molecule.<\/li>\n<\/ol>\n<p><img loading=\"lazy\" decoding=\"async\" src=\"https:\/\/chem.libretexts.org\/LibreTexts\/Athabasca_University\/Chemistry_350%3A_Organic_Chemistry_I\/Chapter_7%3A_Alkenes%3A_Structure_and_Reactivity\/denied:data:image\/png;base64,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#fixme\" alt=\"\" width=\"162\" height=\"62\" \/><\/p>\n<p>In this diagram this is a cis conformation. It has both the substituents going upward. This molecule would be called (cis) 5-chloro-3-heptene.)<\/p>\n<p>Trans would look like this<\/p>\n<p>v. On the other hand if there are 3 or 4 non-hydrogen different atoms attached to the alkene then use the E, Z system.<\/p>\n<p>E (entgegen) means the higher priority groups are opposite one another relative to the double bond.<\/p>\n<p>Z (zusammen) means the higher priority groups are on the same side relative to the double bond.<\/p>\n<p>(You could think of Z as Zame Zide to help memorize it.)<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" src=\"https:\/\/chem.libretexts.org\/LibreTexts\/Athabasca_University\/Chemistry_350%3A_Organic_Chemistry_I\/Chapter_7%3A_Alkenes%3A_Structure_and_Reactivity\/denied:data:image\/png;base64,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#fixme\" alt=\"\" width=\"166\" height=\"64\" \/><\/p>\n<p>In this example it is E-4-chloro-3-heptene. It is E because the Chlorine and the CH<sub>2<\/sub>CH<sub>3<\/sub> are the two higher priorities and they are on opposite sides.<\/p>\n<p>vi. A hydroxyl group gets precedence over th double bond. Therefore alkenes containing alchol groups are called alkenols. And the prefix becomes &#8211;enol. And this means that now the alcohol gets lowest priority over the alkene.<\/p>\n<p>vii. Lastly remember that alkene substituents are called alkenyl. Suffix &#8211;enyl.<\/p>\n<p>Here is a chart containing the systemic name for the first twenty straight chain alkenes.<\/p>\n<table style=\"margin: auto;border-spacing: 1px\" cellpadding=\"1\">\n<caption><em><strong>Table 7.3.1<\/strong>: systemic name for the first twenty straight chain alkenes.<\/em><\/caption>\n<tbody>\n<tr>\n<td><strong>Name<\/strong><\/td>\n<td><strong>Molecular formula<\/strong><\/td>\n<\/tr>\n<tr>\n<td>Ethene<\/td>\n<td>C<sub>2<\/sub>H<sub>4<\/sub><\/td>\n<\/tr>\n<tr>\n<td>Propene<\/td>\n<td>C<sub>3<\/sub>H<sub>6<\/sub><\/td>\n<\/tr>\n<tr>\n<td>Butene<\/td>\n<td>C<sub>4<\/sub>H<sub>8<\/sub><\/td>\n<\/tr>\n<tr>\n<td>\u00a0Pentene<\/td>\n<td>\u00a0C<sub>5<\/sub>H<sub>10<\/sub><\/td>\n<\/tr>\n<tr>\n<td>\u00a0Hexene<\/td>\n<td>\u00a0C<sub>6<\/sub>H<sub>12<\/sub><\/td>\n<\/tr>\n<tr>\n<td>\u00a0Heptene<\/td>\n<td>\u00a0C<sub>7<\/sub>H<sub>14<\/sub><\/td>\n<\/tr>\n<tr>\n<td>\u00a0Octene<\/td>\n<td>\u00a0C<sub>8<\/sub>H<sub>16<\/sub><\/td>\n<\/tr>\n<tr>\n<td>\u00a0Nonene<\/td>\n<td>\u00a0C<sub>9<\/sub>H<sub>18<\/sub><\/td>\n<\/tr>\n<tr>\n<td>\u00a0Decene<\/td>\n<td>\u00a0C<sub>10<\/sub>H<sub>20<\/sub><\/td>\n<\/tr>\n<tr>\n<td>\u00a0Undecene<\/td>\n<td>\u00a0C<sub>11<\/sub>H<sub>22<\/sub><\/td>\n<\/tr>\n<tr>\n<td>\u00a0Dodecene<\/td>\n<td>\u00a0C<sub>12<\/sub>H<sub>24<\/sub><\/td>\n<\/tr>\n<tr>\n<td>\u00a0Tridecene<\/td>\n<td>\u00a0C<sub>13<\/sub>H<sub>26<\/sub><\/td>\n<\/tr>\n<tr>\n<td>\u00a0Tetradecene<\/td>\n<td>\u00a0C<sub>14<\/sub>H<sub>28<\/sub><\/td>\n<\/tr>\n<tr>\n<td>\u00a0Pentadecene<\/td>\n<td>\u00a0C<sub>15<\/sub>H<sub>30<\/sub><\/td>\n<\/tr>\n<tr>\n<td>\u00a0Hexadecene<\/td>\n<td>\u00a0C<sub>16<\/sub>H<sub>32<\/sub><\/td>\n<\/tr>\n<tr>\n<td>Heptadecene<\/td>\n<td>C<sub>17<\/sub>H<sub>34<\/sub><\/td>\n<\/tr>\n<tr>\n<td>\u00a0Octadecene<\/td>\n<td>\u00a0C<sub>18<\/sub>H<sub>36<\/sub><\/td>\n<\/tr>\n<tr>\n<td>\u00a0Nonadecene<\/td>\n<td>\u00a0C<sub>19<\/sub>H<sub>38<\/sub><\/td>\n<\/tr>\n<tr>\n<td>\u00a0Eicosene<\/td>\n<td>\u00a0C<sub>20<\/sub>H<sub>40<\/sub><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p>Did you notice how there is no methene? Because it is impossible for a Carbon to have a double bond with nothing.<\/p>\n<\/div>\n<div id=\"section_3\">\n<h3 class=\"editable\">Geometric Isomers<\/h3>\n<p>Double bonds can exist as geometric isomers and these isomers are designated by using either the cis \/ trans designation or the modern E \/ Z designation.<\/p>\n<div id=\"section_4\">\n<h4 class=\"editable\"><em>cis <\/em>Isomers<\/h4>\n<p>.The two largest groups are on the same side of the double bond.<\/p>\n<p><img decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135124\/alkenenomenclature9.gif\" alt=\"\" width=\"85px\" height=\"85px\" \/><\/p>\n<\/div>\n<div id=\"section_5\">\n<h4 class=\"editable\"><em>trans <\/em>Isomers<\/h4>\n<p>&#8230;The two largest groups are on opposite sides of the double bond.<\/p>\n<p><img decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135124\/alkenenomenclature10.gif\" alt=\"\" width=\"85px\" height=\"85px\" \/><\/p>\n<\/div>\n<\/div>\n<div id=\"section_6\">\n<h3 class=\"editable\">E\/Z nomenclature<\/h3>\n<p>E = entgegan (&#8220;trans&#8221;) Z = zusamen (&#8220;cis&#8221;)<\/p>\n<p>Priority of groups is based on the atomic mass of attached atoms (not the size of the group). An atom attached by a multiple bond is counted once for each bond.<\/p>\n<p>fluorine atom &gt; isopropyl group &gt; n-hexyl group<\/p>\n<p>deuterium atom &gt; hydrogen atom<\/p>\n<p>-CH<sub>2<\/sub>-CH=CH<sub>2<\/sub> &gt; -CH<sub>2<\/sub>CH<sub>2<\/sub>CH<sub>3<\/sub><\/p>\n<div class=\"textbox examples\">\n<h3>Example<\/h3>\n<p>Try to name the following compounds using both conventions&#8230;<\/p>\n<p><img decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135125\/alkenenomenclature11.gif\" alt=\"\" width=\"198px\" height=\"117px\" \/><\/p>\n<p><img decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135127\/alkenenomenclature12.gif\" alt=\"\" width=\"198px\" height=\"144px\" \/><\/p>\n<\/div>\n<\/div>\n<div id=\"section_7\">\n<h3 class=\"editable\">Common names<\/h3>\n<p>Remove the -ane suffix and add -ylene. There are a couple of unique ones like ethenyl&#8217;s common name is vinyl and 2-propenyl&#8217;s common name is allyl. That you should know are&#8230;<\/p>\n<ul>\n<li>vinyl substituent H<sub>2<\/sub>C=CH-<\/li>\n<li>allyl substituent H<sub>2<\/sub>C=CH-CH<sub>2<\/sub>&#8211;<\/li>\n<li>allene molecule H<sub>2<\/sub>C=C=CH<sub>2<\/sub><\/li>\n<li>isoprene<\/li>\n<\/ul>\n<p><img decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135128\/alkenenomenclature4.gif\" alt=\"\" width=\"137px\" height=\"119px\" \/><\/p>\n<\/div>\n<div id=\"section_8\">\n<h3 class=\"editable\">Endocyclic Alkenes<\/h3>\n<p>Endocyclic double bonds have both carbons in the ring and exocyclic double bonds have only one carbon as part of the ring.<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135129\/cycloalkane.jpg\" alt=\"cycloalkane.jpg\" width=\"332px\" height=\"247px\" \/><\/p>\n<p>Cyclopentene is an example of an endocyclic double bond.<\/p>\n<p><img decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135131\/alkenenomenclature5.gif\" alt=\"\" width=\"61px\" height=\"65px\" \/><\/p>\n<p>Methylenecylopentane is an example of an exocyclic double bond.<\/p>\n<p><img decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135131\/alkenenomenclature6.gif\" alt=\"\" width=\"120px\" height=\"58px\" \/><\/p>\n<p>Name the following compounds&#8230;<\/p>\n<p><img decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135132\/alkenenomenclature7.gif\" alt=\"\" width=\"91px\" height=\"78px\" \/><\/p>\n<p>1-methylcyclobutene. The methyl group places the double bond. It is correct to also name this compound as 1-methylcyclobut-1-ene.<\/p>\n<p><img decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135134\/alkenenomenclature8.gif\" alt=\"\" width=\"172px\" height=\"82px\" \/><\/p>\n<p>1-ethenylcyclohexene, the methyl group places the double bond. It is correct to also name this compound as 1-ethenylcyclohex-1-ene. A common name would be 1-vinylcyclohexene.<\/p>\n<p>Try to draw structures for the following compounds&#8230;<\/p>\n<p><a class=\"external\" href=\"http:\/\/chemistry.boisestate.edu\/richardbanks\/organic\/nomenclature\/alkenenomenclature10.htm\" target=\"_blank\" rel=\"external nofollow noopener\"><img decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135135\/alkenenomenclature14.gif\" alt=\"\" width=\"222px\" height=\"93px\" \/>\u00a0 <\/a><\/p>\n<ul>\n<li>\u00a02-vinyl-1,3-cyclohexadiene<\/li>\n<\/ul>\n<p><a class=\"external\" href=\"http:\/\/chemistry.boisestate.edu\/richardbanks\/organic\/nomenclature\/alkenenomenclature11.htm\" target=\"_blank\" rel=\"external nofollow noopener\"><img decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135136\/alkenenomenclature15.gif\" alt=\"\" width=\"180px\" height=\"82px\" \/>\u00a0 <\/a><\/p>\n<\/div>\n<div id=\"section_9\">\n<div class=\"textbox examples\">\n<h3>Examples<\/h3>\n<p style=\"text-align: center\"><img decoding=\"async\" class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135138\/nomprb7.gif\" alt=\"image\" \/><\/p>\n<p>Both these compounds have double bonds, making them alkenes. In example (1) the longest chain consists of six carbons, so the root name of this compound will be hexene. Three methyl substituents (colored red) are present. Numbering the six-carbon chain begins at the end nearest the double bond (the left end), so the methyl groups are located on carbons 2 &amp; 5. The IUPAC name is therefore: 2,5,5-trimethyl-2-hexene.<\/p>\n<p>In example (2) the longest chain incorporating both carbon atoms of the double bond has a length of five. There is a seven-carbon chain, but it contains only one of the double bond carbon atoms. Consequently, the root name of this compound will be pentene. There is a propyl substituent on the inside double bond carbon atom (#2), so the IUPAC name is: 2-propyl-1-pentene.<\/p>\n<p style=\"text-align: center\"><img decoding=\"async\" class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135140\/nomprb8.gif\" alt=\"image\" \/><\/p>\n<p>The double bond in example (3) is located in the center of a six-carbon chain. The double bond would therefore have a locator number of 3 regardless of the end chosen to begin numbering. The right hand end is selected because it gives the lowest first-substituent number (2 for the methyl as compared with 3 for the ethyl if numbering were started from the left). The IUPAC name is assigned as shown.<\/p>\n<p>Example (4) is a diene (two double bonds). Both double bonds must be contained in the longest chain, which is therefore five- rather than six-carbons in length. The second and fourth carbons of this 1,4-pentadiene are both substituted, so the numbering begins at the end nearest the alphabetically first-cited substituent (the ethyl group).<\/p>\n<p style=\"text-align: center\"><img decoding=\"async\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135143\/nomprb9.gif\" alt=\"image\" \/><\/p>\n<p>These examples include rings of carbon atoms as well as some carbon-carbon triple bonds. Example (6) is best named as an alkyne bearing a cyclobutyl substituent. Example (7) is simply a ten-membered ring containing both a double and a triple bond. The double bond is cited first in the IUPAC name, so numbering begins with those two carbons in the direction that gives the triple bond carbons the lowest locator numbers. Because of the linear geometry of a triple bond, a-ten membered ring is the smallest ring in which this functional group is easily accommodated. Example (8) is a cyclooctatriene (three double bonds in an eight-membered ring). The numbering must begin with one of the end carbons of the conjugated diene moiety (adjacent double bonds), because in this way the double bond carbon atoms are assigned the smallest possible locator numbers (1, 2, 3, 4, 6 &amp; 7). Of the two ways in which this can be done, we choose the one that gives the vinyl substituent the lower number.<\/p>\n<\/div>\n<\/div>\n<div id=\"section_10\">\n<h3 class=\"editable\">Outside links<\/h3>\n<ul>\n<li><a class=\"external\" title=\"http:\/\/www.vanderbilt.edu\/AnS\/Chemistry\/Rizzo\/chem220a\/alkenes.pdf\" href=\"http:\/\/www.vanderbilt.edu\/AnS\/Chemistry\/Rizzo\/chem220a\/alkenes.pdf\" rel=\"freeklink\">http:\/\/www.vanderbilt.edu\/AnS\/Chemis&#8230;0a\/alkenes.pdf<\/a><\/li>\n<\/ul>\n<\/div>\n<div id=\"section_11\">\n<h3 class=\"editable\">References<\/h3>\n<ol>\n<li>Vollhardt, Peter, and Neil E. Schore. <u>Organic\u00a0Chemistry:\u00a0Structure and Function<\/u>.\u00a05th Edition.\u00a0New York:\u00a0W.\u00a0H. Freeman &amp;\u00a0Company, 2007.<\/li>\n<\/ol>\n<\/div>\n<div id=\"section_12\">\n<div class=\"textbox examples\">\n<h3>Examples<\/h3>\n<div id=\"section_12\">\n<h3 class=\"editable\">Problems<\/h3>\n<p>1. Try to name the following compounds&#8230;<\/p>\n<p><img decoding=\"async\" class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135145\/alkenenomenclature1.gif\" alt=\"image\" \/><\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135147\/alkenenomenclature2.gif\" alt=\"\" width=\"322px\" height=\"87px\" \/><\/p>\n<p>2. Try to draw structures for the following compounds&#8230;<\/p>\n<ul>\n<li>\u00a02-pentene<\/li>\n<li>\u00a03-heptene<\/li>\n<\/ul>\n<p>3. Give the double bond the lowest possible numbers regardless of substituent placement.<\/p>\n<p>\u2022 Try to name the following compound&#8230;<\/p>\n<p><img decoding=\"async\" class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135148\/alkenenomenclature3.gif\" alt=\"image\" \/><\/p>\n<p>\u2022 Try to draw a structure for the following compound&#8230;<\/p>\n<p>4-methyl-2-pentene<\/p>\n<p>4. Name the following structures:<\/p>\n<p><img decoding=\"async\" class=\"internal left aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135150\/alkene_problem_2.jpg\" alt=\"alkene problem 2.jpg\" width=\"348px\" height=\"217px\" \/><\/p>\n<p>5. Draw (Z)-5-Chloro-3-ethly-4-hexen-2-ol<\/p>\n<\/div>\n<div id=\"section_13\">\n<h3 class=\"editable\">Answers<\/h3>\n<p class=\"editable\">\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q699159\">Show Answer<\/span><\/p>\n<div id=\"q699159\" class=\"hidden-answer\" style=\"display: none\">\n<p>1.1-pentene or pent-1-ene; 2-ethyl-1-hexene or 2-ethylhex-1-ene<\/p>\n<p>2. CH3\u2013CH=CH\u2013CH2\u2013CH3; CH3\u2013CH2\u2013CH=CH\u2013CH2\u2013CH2\u2013CH3<\/p>\n<p>3.\u00a04-methyl-1-pentene; CH3\u2013CH=CH\u2013CH(CH3)\u2013CH3<\/p>\n<p>4.(I) trans-8-ethyl-3-undecene; (II) E-5-bromo-4-chloro-7,7-dimethyl-4-undecene;(III) Z-1,2-difluoro-cyclohexene; (IV) 4-ethenylcyclohexanol<\/p>\n<p>5.<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135155\/alkene9.jpg\" alt=\"alkene9.jpg\" width=\"334px\" height=\"208px\" \/><\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_14\">\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>S. Devarajan (UCD)<\/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<\/ul>\n<ul>\n<li><a class=\"external\" title=\"https:\/\/chemistry.boisestate.edu\/richardbanks\/rcb2.htm\" href=\"http:\/\/chemistry.boisestate.edu\/richardbanks\/rcb2.htm\" target=\"_blank\" rel=\"external nofollow noopener\">Richard Banks<\/a> (<a class=\"external\" title=\"https:\/\/chemistry.boisestate.edu\/\" href=\"http:\/\/chemistry.boisestate.edu\/\" target=\"_blank\" rel=\"external nofollow noopener\">Boise State University<\/a>)<\/li>\n<\/ul>\n<\/div>\n<\/div>\n","protected":false},"author":44985,"menu_order":4,"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-960","chapter","type-chapter","status-publish","hentry"],"part":23,"_links":{"self":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/960","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\/44985"}],"version-history":[{"count":5,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/960\/revisions"}],"predecessor-version":[{"id":2278,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/960\/revisions\/2278"}],"part":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/parts\/23"}],"metadata":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/960\/metadata\/"}],"wp:attachment":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/media?parent=960"}],"wp:term":[{"taxonomy":"chapter-type","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapter-type?post=960"},{"taxonomy":"contributor","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/contributor?post=960"},{"taxonomy":"license","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/license?post=960"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}