{"id":544,"date":"2017-10-04T20:57:54","date_gmt":"2017-10-04T20:57:54","guid":{"rendered":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/?post_type=chapter&#038;p=544"},"modified":"2018-10-03T17:25:42","modified_gmt":"2018-10-03T17:25:42","slug":"conformers-of-other-alkanes","status":"publish","type":"chapter","link":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/chapter\/conformers-of-other-alkanes\/","title":{"raw":"Conformers of Other Alkanes","rendered":"Conformers of Other 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>depict the staggered and eclipsed conformers of propane (or a similar compound) using sawhorse representations and Newman projections.<\/li>\r\n \t<li>sketch a graph of energy versus bond rotation for propane (or a similar compound) and discuss the graph in terms of torsional strain.<\/li>\r\n \t<li>depict the anti, gauche, eclipsed and fully eclipsed conformers of butane (or a similar compound), using sawhorse representations and Newman projections.<\/li>\r\n \t<li>sketch a graph of energy versus ($\\ce{\\sf{C{2}-C{3}}}$) bond rotation for butane (or a similar compound), and discuss it in terms of torsional and steric repulsion.<\/li>\r\n \t<li>assess which of two (or more) conformers of a given compound is likely to predominate at room temperature from a semi-quantitative knowledge of the energy costs of the interactions involved.<\/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 class=\"textbox key-takeaways\">\r\n<h3>Key Terms<\/h3>\r\nMake certain that you can define, and use in context, the key terms below.\r\n<ul>\r\n \t<li>anti conformation<\/li>\r\n \t<li>gauche conformation<\/li>\r\n \t<li>eclipsed conformation<\/li>\r\n \t<li>steric repulsion<\/li>\r\n<\/ul>\r\n<\/div>\r\n<\/div>\r\nIn butane, there are now three rotating carbon-carbon bonds to consider, but we will focus on the middle bond between C<sub>2<\/sub> and C<sub>3<\/sub>. Below are two representations of butane in a conformation which puts the two CH<sub>3<\/sub> groups (C<sub>1<\/sub> and C<sub>4<\/sub>) in the eclipsed position.\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\/04205713\/image014.png\" alt=\"image014.png\" width=\"377\" height=\"131\" \/>\r\n\r\nThis is the highest energy conformation for butane, due to what is called \u2018<strong>van der Waals repulsion<\/strong>\u2019, or \u2018<strong>steric repulsion\u2019<\/strong>, between the two rather bulky methyl groups.\r\n\r\nWhat is van der Waals repulsion? Didn\u2019t we just learn in Chapter 2 that the van der Waals force between two nonpolar groups is an <em>attractive<\/em> force? Consider this: you probably like to be near your friends, but no matter how close you are you probably don\u2019t want to share a one-room apartment with five of them. When the two methyl groups are brought too close together, the overall resulting noncovalent interaction is repulsive rather than attractive. The result is that their respective electron densities repel one another.\r\n\r\nIf we rotate the front, (blue) carbon by 60\u00b0clockwise, the butane molecule is now in a staggered conformation.\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\/04205716\/image016.png\" alt=\"image016.png\" width=\"378\" height=\"133\" \/>\r\n\r\nThis is more specifically referred to as the \u2018<strong>gauche\u2019<\/strong> conformation of butane. Notice that although they are staggered, the two methyl groups are not as far apart as they could possibly be. There is still significant steric repulsion between the two bulky groups. A further rotation of 60\u00b0gives us a second eclipsed conformation (B) in which both methyl groups are lined up with hydrogen atoms.\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\/04205719\/image018.png\" alt=\"image018.png\" width=\"381\" height=\"131\" \/>\r\n\r\nDue to steric repulsion between methyl and hydrogen substituents, this eclipsed conformation B is higher in energy than the gauche conformation. However, because there is no methyl-to-methyl eclipsing, it is lower in energy than eclipsed conformation A.\r\n\r\nOne more 60 rotation produces the \u2018anti\u2019 conformation, where the two methyl groups are positioned opposite each other and steric repulsion is minimized.\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\/04205721\/image020.png\" alt=\"image020.png\" width=\"358\" height=\"131\" \/>\r\n\r\nThis is the lowest energy conformation for butane.\r\n\r\nThe diagram below summarizes the relative energies for the various eclipsed, staggered, and gauche conformations.\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\/04205724\/image022.png\" alt=\"image022.png\" width=\"498\" height=\"346\" \/>\r\n\r\nAt room temperature, butane is most likely to be in the lowest-energy anti conformation at any given moment in time, although the energy barrier between the anti and eclipsed conformations is not high enough to prevent constant rotation except at very low temperatures. For this reason (and also simply for ease of drawing), it is conventional to draw straight-chain alkanes in a zigzag form, which implies anti conformation at all carbon-carbon bonds.\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\/04205727\/image024.png\" alt=\"image024.png\" width=\"465\" height=\"116\" \/>\r\n<div style=\"margin: auto\"><\/div>\r\n<div>\r\n<div id=\"example\">\r\n<div class=\"textbox examples\">\r\n<h3>Example<\/h3>\r\nDraw Newman projections of the eclipsed and staggered conformations of propane.\r\n<div>\r\n<dl>\r\n \t<dt><strong class=\"emphasis bold\">Answer:<\/strong><\/dt>\r\n \t<dd><a class=\"thumb\" title=\"\" href=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/108714\/3-7-1.jpg?revision=1\" rel=\"internal\"><img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04205729\/3-7-1.jpg\" alt=\"\" width=\"385px\" height=\"361px\" \/><\/a><\/dd>\r\n<\/dl>\r\n<\/div>\r\n<\/div>\r\n<div><\/div>\r\n<\/div>\r\n<\/div>\r\n<div>\r\n<div class=\"textbox examples\">\r\n<h3>Example<\/h3>\r\nDraw a Newman projection, looking down the C<sub>2<\/sub>-C<sub>3<\/sub> bond, of 1-butene in the conformation shown below.\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\/04205731\/image026.png\" alt=\"image026.png\" width=\"134\" height=\"89\" \/>\r\n<div>\r\n<dl>\r\n \t<dt><strong class=\"emphasis bold\">Answer:<\/strong><\/dt>\r\n \t<dd><a class=\"thumb\" title=\"\" href=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/107724\/3-7-2.png?revision=1\" rel=\"internal\"><img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04205733\/3-7-2.png\" alt=\"\" width=\"350px\" height=\"162px\" \/><\/a><\/dd>\r\n<\/dl>\r\n<\/div>\r\n<\/div>\r\n<div><\/div>\r\n<\/div>\r\nThe following diagram illustrates the change in potential energy that occurs with rotation about the C<sub>2<\/sub>\u2013C<sub>3<\/sub> bond.\r\n\r\n[caption id=\"\" align=\"aligncenter\" width=\"480\"]<img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04205735\/butdihed.gif\" alt=\"butdihed.gif\" width=\"480\" height=\"378\" \/> Figure X: Potential curve vs dihedral angle of the C2-C3 bond of butane.[\/caption]\r\n\r\n<div id=\"section_1\">\r\n<h3 class=\"editable\">Exercises<\/h3>\r\n<div id=\"s61690\">\r\n<div id=\"section_24\">\r\n<div class=\"textbox exercises\">\r\n<h3>Exercises<\/h3>\r\n<div id=\"section_1\">\r\n<div id=\"s61690\">\r\n<div id=\"section_24\">\r\n<h3 id=\"Questions-61690\">Question<\/h3>\r\nDraw the energy diagram for the rotation of the bond highlighted in pentane.\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\/04205737\/3-7qu.png\" alt=\"\" width=\"142\" height=\"32\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_25\">\r\n<h3 id=\"Solutions-61690\">Solution<\/h3>\r\n<strong>\r\n[reveal-answer q=\"955597\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"955597\"]<a class=\"thumb\" title=\"\" href=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/108651\/3.7.jpg?revision=1\" rel=\"internal\">\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04205739\/3.7.jpg\" alt=\"\" width=\"350px\" height=\"260px\" \/><\/a><\/strong>\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\/04205741\/3-7sol.png\" alt=\"\" width=\"551\" height=\"308\" \/>\r\n<strong>[\/hidden-answer]<\/strong>\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_2\">\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 \t<li>Jim Clark (<a class=\"external\" title=\"http:\/\/www.chemguide.co.uk\" href=\"http:\/\/www.chemguide.co.uk\" target=\"_blank\" rel=\"external nofollow noopener\">Chemguide.co.uk<\/a>)<\/li>\r\n \t<li>William Reusch, Professor Emeritus (<a class=\"external\" title=\"http:\/\/www.msu.edu\/\" href=\"http:\/\/www.msu.edu\/\" target=\"_blank\" rel=\"external nofollow noopener\">Michigan State U.<\/a>), <a class=\"external\" title=\"http:\/\/www.cem.msu.edu\/~reusch\/VirtualText\/intro1.htm\" href=\"http:\/\/www.cem.msu.edu\/%7Ereusch\/VirtualText\/intro1.htm\" target=\"_blank\" rel=\"external nofollow noopener\">Virtual Textbook of\u00a0Organic\u00a0Chemistry<\/a><\/li>\r\n<\/ul>\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>depict the staggered and eclipsed conformers of propane (or a similar compound) using sawhorse representations and Newman projections.<\/li>\n<li>sketch a graph of energy versus bond rotation for propane (or a similar compound) and discuss the graph in terms of torsional strain.<\/li>\n<li>depict the anti, gauche, eclipsed and fully eclipsed conformers of butane (or a similar compound), using sawhorse representations and Newman projections.<\/li>\n<li>sketch a graph of energy versus ($\\ce{\\sf{C{2}-C{3}}}$) bond rotation for butane (or a similar compound), and discuss it in terms of torsional and steric repulsion.<\/li>\n<li>assess which of two (or more) conformers of a given compound is likely to predominate at room temperature from a semi-quantitative knowledge of the energy costs of the interactions involved.<\/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 class=\"textbox key-takeaways\">\n<h3>Key Terms<\/h3>\n<p>Make certain that you can define, and use in context, the key terms below.<\/p>\n<ul>\n<li>anti conformation<\/li>\n<li>gauche conformation<\/li>\n<li>eclipsed conformation<\/li>\n<li>steric repulsion<\/li>\n<\/ul>\n<\/div>\n<\/div>\n<p>In butane, there are now three rotating carbon-carbon bonds to consider, but we will focus on the middle bond between C<sub>2<\/sub> and C<sub>3<\/sub>. Below are two representations of butane in a conformation which puts the two CH<sub>3<\/sub> groups (C<sub>1<\/sub> and C<sub>4<\/sub>) in the eclipsed position.<\/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\/04205713\/image014.png\" alt=\"image014.png\" width=\"377\" height=\"131\" \/><\/p>\n<p>This is the highest energy conformation for butane, due to what is called \u2018<strong>van der Waals repulsion<\/strong>\u2019, or \u2018<strong>steric repulsion\u2019<\/strong>, between the two rather bulky methyl groups.<\/p>\n<p>What is van der Waals repulsion? Didn\u2019t we just learn in Chapter 2 that the van der Waals force between two nonpolar groups is an <em>attractive<\/em> force? Consider this: you probably like to be near your friends, but no matter how close you are you probably don\u2019t want to share a one-room apartment with five of them. When the two methyl groups are brought too close together, the overall resulting noncovalent interaction is repulsive rather than attractive. The result is that their respective electron densities repel one another.<\/p>\n<p>If we rotate the front, (blue) carbon by 60\u00b0clockwise, the butane molecule is now in a staggered conformation.<\/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\/04205716\/image016.png\" alt=\"image016.png\" width=\"378\" height=\"133\" \/><\/p>\n<p>This is more specifically referred to as the \u2018<strong>gauche\u2019<\/strong> conformation of butane. Notice that although they are staggered, the two methyl groups are not as far apart as they could possibly be. There is still significant steric repulsion between the two bulky groups. A further rotation of 60\u00b0gives us a second eclipsed conformation (B) in which both methyl groups are lined up with hydrogen atoms.<\/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\/04205719\/image018.png\" alt=\"image018.png\" width=\"381\" height=\"131\" \/><\/p>\n<p>Due to steric repulsion between methyl and hydrogen substituents, this eclipsed conformation B is higher in energy than the gauche conformation. However, because there is no methyl-to-methyl eclipsing, it is lower in energy than eclipsed conformation A.<\/p>\n<p>One more 60 rotation produces the \u2018anti\u2019 conformation, where the two methyl groups are positioned opposite each other and steric repulsion is minimized.<\/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\/04205721\/image020.png\" alt=\"image020.png\" width=\"358\" height=\"131\" \/><\/p>\n<p>This is the lowest energy conformation for butane.<\/p>\n<p>The diagram below summarizes the relative energies for the various eclipsed, staggered, and gauche conformations.<\/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\/04205724\/image022.png\" alt=\"image022.png\" width=\"498\" height=\"346\" \/><\/p>\n<p>At room temperature, butane is most likely to be in the lowest-energy anti conformation at any given moment in time, although the energy barrier between the anti and eclipsed conformations is not high enough to prevent constant rotation except at very low temperatures. For this reason (and also simply for ease of drawing), it is conventional to draw straight-chain alkanes in a zigzag form, which implies anti conformation at all carbon-carbon bonds.<\/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\/04205727\/image024.png\" alt=\"image024.png\" width=\"465\" height=\"116\" \/><\/p>\n<div style=\"margin: auto\"><\/div>\n<div>\n<div id=\"example\">\n<div class=\"textbox examples\">\n<h3>Example<\/h3>\n<p>Draw Newman projections of the eclipsed and staggered conformations of propane.<\/p>\n<div>\n<dl>\n<dt><strong class=\"emphasis bold\">Answer:<\/strong><\/dt>\n<dd><a class=\"thumb\" title=\"\" href=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/108714\/3-7-1.jpg?revision=1\" rel=\"internal\"><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04205729\/3-7-1.jpg\" alt=\"\" width=\"385px\" height=\"361px\" \/><\/a><\/dd>\n<\/dl>\n<\/div>\n<\/div>\n<div><\/div>\n<\/div>\n<\/div>\n<div>\n<div class=\"textbox examples\">\n<h3>Example<\/h3>\n<p>Draw a Newman projection, looking down the C<sub>2<\/sub>-C<sub>3<\/sub> bond, of 1-butene in the conformation shown below.<\/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\/04205731\/image026.png\" alt=\"image026.png\" width=\"134\" height=\"89\" \/><\/p>\n<div>\n<dl>\n<dt><strong class=\"emphasis bold\">Answer:<\/strong><\/dt>\n<dd><a class=\"thumb\" title=\"\" href=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/107724\/3-7-2.png?revision=1\" rel=\"internal\"><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04205733\/3-7-2.png\" alt=\"\" width=\"350px\" height=\"162px\" \/><\/a><\/dd>\n<\/dl>\n<\/div>\n<\/div>\n<div><\/div>\n<\/div>\n<p>The following diagram illustrates the change in potential energy that occurs with rotation about the C<sub>2<\/sub>\u2013C<sub>3<\/sub> bond.<\/p>\n<div style=\"width: 490px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04205735\/butdihed.gif\" alt=\"butdihed.gif\" width=\"480\" height=\"378\" \/><\/p>\n<p class=\"wp-caption-text\">Figure X: Potential curve vs dihedral angle of the C2-C3 bond of butane.<\/p>\n<\/div>\n<div id=\"section_1\">\n<h3 class=\"editable\">Exercises<\/h3>\n<div id=\"s61690\">\n<div id=\"section_24\">\n<div class=\"textbox exercises\">\n<h3>Exercises<\/h3>\n<div id=\"section_1\">\n<div id=\"s61690\">\n<div id=\"section_24\">\n<h3 id=\"Questions-61690\">Question<\/h3>\n<p>Draw the energy diagram for the rotation of the bond highlighted in pentane.<\/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\/04205737\/3-7qu.png\" alt=\"\" width=\"142\" height=\"32\" \/><\/p>\n<\/div>\n<div id=\"section_25\">\n<h3 id=\"Solutions-61690\">Solution<\/h3>\n<p><strong><\/p>\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q955597\">Show Answer<\/span><\/p>\n<div id=\"q955597\" class=\"hidden-answer\" style=\"display: none\"><a class=\"thumb\" title=\"\" href=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/108651\/3.7.jpg?revision=1\" rel=\"internal\"><br \/>\n<img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04205739\/3.7.jpg\" alt=\"\" width=\"350px\" height=\"260px\" \/><\/a><\/strong><\/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\/04205741\/3-7sol.png\" alt=\"\" width=\"551\" height=\"308\" \/><br \/>\n<strong><\/div>\n<\/div>\n<p><\/strong><\/p>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_2\">\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<li>Jim Clark (<a class=\"external\" title=\"http:\/\/www.chemguide.co.uk\" href=\"http:\/\/www.chemguide.co.uk\" target=\"_blank\" rel=\"external nofollow noopener\">Chemguide.co.uk<\/a>)<\/li>\n<li>William Reusch, Professor Emeritus (<a class=\"external\" title=\"http:\/\/www.msu.edu\/\" href=\"http:\/\/www.msu.edu\/\" target=\"_blank\" rel=\"external nofollow noopener\">Michigan State U.<\/a>), <a class=\"external\" title=\"http:\/\/www.cem.msu.edu\/~reusch\/VirtualText\/intro1.htm\" href=\"http:\/\/www.cem.msu.edu\/%7Ereusch\/VirtualText\/intro1.htm\" target=\"_blank\" rel=\"external nofollow noopener\">Virtual Textbook of\u00a0Organic\u00a0Chemistry<\/a><\/li>\n<\/ul>\n<\/div>\n<\/div>\n<\/div>\n","protected":false},"author":311,"menu_order":9,"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-544","chapter","type-chapter","status-publish","hentry"],"part":21,"_links":{"self":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/544","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\/544\/revisions"}],"predecessor-version":[{"id":2246,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/544\/revisions\/2246"}],"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\/544\/metadata\/"}],"wp:attachment":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/media?parent=544"}],"wp:term":[{"taxonomy":"chapter-type","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapter-type?post=544"},{"taxonomy":"contributor","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/contributor?post=544"},{"taxonomy":"license","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/license?post=544"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}