{"id":1006,"date":"2017-10-19T14:41:35","date_gmt":"2017-10-19T14:41:35","guid":{"rendered":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/?post_type=chapter&#038;p=1006"},"modified":"2018-10-03T19:51:00","modified_gmt":"2018-10-03T19:51:00","slug":"stability-of-alkenes","status":"publish","type":"chapter","link":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/chapter\/stability-of-alkenes\/","title":{"raw":"Stability of Alkenes","rendered":"Stability of Alkenes"},"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>explain why cis alkenes are generally less stable than their trans isomers.<\/li>\r\n \t<li>explain that catalytic reduction of a cis alkene produces the same alkane as the catalytic reduction of the trans isomer.<\/li>\r\n \t<li>explain how heats of hydrogenation (<em>\u0394H<\/em>\u00b0<sub>hydrog<\/sub>) can be used to show that cis alkenes are less stable than their trans isomers, and discuss, briefly, the limitations of this approach.<\/li>\r\n \t<li>arrange a series of alkenes in order of increasing or decreasing stability.<\/li>\r\n \t<li>describe, briefly, two of the hypotheses proposed to explain why alkene stability increases with increased substitution.\r\n<blockquote><strong>Note:<\/strong> This problem is a typical example of those instances in science where there is probably no single \u201ccorrect\u201d explanation for an observed phenomenon.<\/blockquote>\r\n<\/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>catalytic hydrogenation<\/li>\r\n \t<li>heat of hydrogenation, (<em>\u0394H<\/em>\u00b0<sub>hydrog<\/sub>)<\/li>\r\n \t<li>hyperconjugation<\/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 two alkenes,\u00a0<em>cis<\/em>\u00a0<span id=\"MathJax-Element-1-Frame\" class=\"MathJax\" role=\"presentation\"><span id=\"MathJax-Span-1\" class=\"math\"><span id=\"MathJax-Span-2\" class=\"mrow\"><span id=\"MathJax-Span-3\" class=\"texatom\"><span id=\"MathJax-Span-4\" class=\"mrow\"><span id=\"MathJax-Span-5\" class=\"msubsup\"><span id=\"MathJax-Span-6\" class=\"mtext\">\ud835\udda2\ud835\udda7<\/span><span id=\"MathJax-Span-7\" class=\"texatom\"><span id=\"MathJax-Span-8\" class=\"mrow\"><span id=\"MathJax-Span-9\" class=\"mspace\"><\/span><\/span><\/span><span id=\"MathJax-Span-10\" class=\"texatom\"><span id=\"MathJax-Span-11\" class=\"mrow\"><span id=\"MathJax-Span-12\" class=\"mn\">\ud835\udfe5<\/span><\/span><\/span><\/span><span id=\"MathJax-Span-13\" class=\"mtext\">\ud835\udda2\ud835\udda7<\/span><span id=\"MathJax-Span-14\" class=\"texatom\"><span id=\"MathJax-Span-15\" class=\"mrow\"><span id=\"MathJax-Span-16\" class=\"mo\">=<\/span><\/span><\/span><span id=\"MathJax-Span-17\" class=\"msubsup\"><span id=\"MathJax-Span-18\" class=\"mtext\">\ud835\udda2\ud835\udda7\ud835\udda2\ud835\udda7<\/span><span id=\"MathJax-Span-19\" class=\"texatom\"><span id=\"MathJax-Span-20\" class=\"mrow\"><span id=\"MathJax-Span-21\" class=\"mspace\"><\/span><\/span><\/span><span id=\"MathJax-Span-22\" class=\"texatom\"><span id=\"MathJax-Span-23\" class=\"mrow\"><span id=\"MathJax-Span-24\" class=\"mn\">\ud835\udfe5<\/span><\/span><\/span><\/span><\/span><\/span><\/span><\/span><span class=\"MJX_Assistive_MathML\" role=\"presentation\">CH3CH=CHCH3<\/span><\/span>\u00a0and\u00a0<span id=\"MathJax-Element-2-Frame\" class=\"MathJax\" role=\"presentation\"><span id=\"MathJax-Span-25\" class=\"math\"><span id=\"MathJax-Span-26\" class=\"mrow\"><span id=\"MathJax-Span-27\" class=\"texatom\"><span id=\"MathJax-Span-28\" class=\"mrow\"><span id=\"MathJax-Span-29\" class=\"msubsup\"><span id=\"MathJax-Span-30\" class=\"texatom\"><span id=\"MathJax-Span-31\" class=\"mrow\"><span id=\"MathJax-Span-32\" class=\"mo\">(<\/span><span id=\"MathJax-Span-33\" class=\"msubsup\"><span id=\"MathJax-Span-34\" class=\"mtext\">\ud835\udda2\ud835\udda7<\/span><span id=\"MathJax-Span-35\" class=\"texatom\"><span id=\"MathJax-Span-36\" class=\"mrow\"><span id=\"MathJax-Span-37\" class=\"mspace\"><\/span><\/span><\/span><span id=\"MathJax-Span-38\" class=\"texatom\"><span id=\"MathJax-Span-39\" class=\"mrow\"><span id=\"MathJax-Span-40\" class=\"mn\">\ud835\udfe5<\/span><\/span><\/span><\/span><span id=\"MathJax-Span-41\" class=\"mo\">)<\/span><\/span><\/span><span id=\"MathJax-Span-42\" class=\"texatom\"><span id=\"MathJax-Span-43\" class=\"mrow\"><span id=\"MathJax-Span-44\" class=\"mspace\"><\/span><\/span><\/span><span id=\"MathJax-Span-45\" class=\"texatom\"><span id=\"MathJax-Span-46\" class=\"mrow\"><span id=\"MathJax-Span-47\" class=\"mn\">\ud835\udfe4<\/span><\/span><\/span><\/span><span id=\"MathJax-Span-48\" class=\"mtext\">\ud835\udda2<\/span><span id=\"MathJax-Span-49\" class=\"texatom\"><span id=\"MathJax-Span-50\" class=\"mrow\"><span id=\"MathJax-Span-51\" class=\"mo\">=<\/span><\/span><\/span><span id=\"MathJax-Span-52\" class=\"msubsup\"><span id=\"MathJax-Span-53\" class=\"mtext\">\ud835\udda2\ud835\udda7<\/span><span id=\"MathJax-Span-54\" class=\"texatom\"><span id=\"MathJax-Span-55\" class=\"mrow\"><span id=\"MathJax-Span-56\" class=\"mspace\"><\/span><\/span><\/span><span id=\"MathJax-Span-57\" class=\"texatom\"><span id=\"MathJax-Span-58\" class=\"mrow\"><span id=\"MathJax-Span-59\" class=\"mn\">\ud835\udfe4<\/span><\/span><\/span><\/span><\/span><\/span><\/span><\/span><span class=\"MJX_Assistive_MathML\" role=\"presentation\">(CH3)2C=CH2<\/span><\/span>\u00a0have similar heats of hydrogenation (\u2212120 kJ\/mol and \u2212119 kJ\/mol, respectively), and are therefore of similar stability. However, they are both less stable than\u00a0<em>trans<\/em>\u00a0<span id=\"MathJax-Element-3-Frame\" class=\"MathJax\" role=\"presentation\"><span id=\"MathJax-Span-60\" class=\"math\"><span id=\"MathJax-Span-61\" class=\"mrow\"><span id=\"MathJax-Span-62\" class=\"texatom\"><span id=\"MathJax-Span-63\" class=\"mrow\"><span id=\"MathJax-Span-64\" class=\"msubsup\"><span id=\"MathJax-Span-65\" class=\"mtext\">\ud835\udda2\ud835\udda7<\/span><span id=\"MathJax-Span-66\" class=\"texatom\"><span id=\"MathJax-Span-67\" class=\"mrow\"><span id=\"MathJax-Span-68\" class=\"mspace\"><\/span><\/span><\/span><span id=\"MathJax-Span-69\" class=\"texatom\"><span id=\"MathJax-Span-70\" class=\"mrow\"><span id=\"MathJax-Span-71\" class=\"mn\">\ud835\udfe5<\/span><\/span><\/span><\/span><span id=\"MathJax-Span-72\" class=\"mtext\">\ud835\udda2\ud835\udda7<\/span><span id=\"MathJax-Span-73\" class=\"texatom\"><span id=\"MathJax-Span-74\" class=\"mrow\"><span id=\"MathJax-Span-75\" class=\"mo\">=<\/span><\/span><\/span><span id=\"MathJax-Span-76\" class=\"msubsup\"><span id=\"MathJax-Span-77\" class=\"mtext\">\ud835\udda2\ud835\udda7\ud835\udda2\ud835\udda7<\/span><span id=\"MathJax-Span-78\" class=\"texatom\"><span id=\"MathJax-Span-79\" class=\"mrow\"><span id=\"MathJax-Span-80\" class=\"mspace\"><\/span><\/span><\/span><span id=\"MathJax-Span-81\" class=\"texatom\"><span id=\"MathJax-Span-82\" class=\"mrow\"><span id=\"MathJax-Span-83\" class=\"mn\">\ud835\udfe5<\/span><\/span><\/span><\/span><\/span><\/span><\/span><\/span><span class=\"MJX_Assistive_MathML\" role=\"presentation\">CH3CH=CHCH3<\/span><\/span>\u00a0(\u2212116 kJ\/mol).\r\n\r\nYou may wonder why an <em>sp<\/em><sup>2<\/sup>\u00a0-<em>sp<\/em><sup>3<\/sup> bond is stronger than an sp<sup>3<\/sup>-sp<sup>3<\/sup> bond. Bond strength depends on the efficiency with which orbitals can overlap. In general, <em>s<\/em>\u00a0orbitals overlap more efficiently than do <em>p<\/em>\u00a0orbitals; therefore, the <em>s<\/em>-<em>s<\/em> bond in the hydrogen molecule is stronger than the <em>p<\/em>-<em>p<\/em> bond in fluorine. In hybrid orbitals, the greater the <em>s<\/em> character of the orbital, the more efficiently it can overlap: an <em>sp<\/em><sup>2<\/sup> orbital, which has a 33% <em>s<\/em> character, can overlap more effectively than an <em>sp<\/em><sup>3<\/sup> orbital, with only 25% <em>s<\/em> character.\r\n\r\n<\/div>\r\n<\/div>\r\nAlkene hydrogenation is the <span class=\"external\">syn-addition<\/span> of hydrogen to an <a title=\"Organic Chemistry\/Hydrocarbons\/Alkenes\" href=\"https:\/\/chem.libretexts.org\/Core\/Organic_Chemistry\/Hydrocarbons\/Alkenes\" rel=\"internal\"><span class=\"external\">alkene<\/span><\/a>, saturating the bond.\u00a0 The alkene reacts with hydrogen gas in the presence of a metal catalyst which allows the reaction to occur quickly. The energy released in this process, called the heat of <span class=\"external\">hydrogenation<\/span>,\u00a0 indicates the relative stability of the double bond in the molecule (see <a title=\"Organic Chemistry\/Hydrocarbons\/Alkenes\/Catalytic Hydrogenation\" rel=\"broken\"><span class=\"external\">Catalytic Hydrogenation<\/span><\/a>).\r\n<div id=\"section_1\">\r\n<h3 class=\"editable\">Introduction<\/h3>\r\nThe reaction begins with H<sub>2<\/sub> gas and an alkene (a carbon-carbon double bond). The <span class=\"external\">pi bond<\/span> in the alkene acts as a nucleophile; the two electrons in it form a sigma bond with one of the hydrogen atoms in H<sub>2<\/sub>. With the pi bond broken, the other carbon (the one that did not newly receive a hydrogen) is left with a positive formal charge. This is the carbocation intermediate. The remaining (unreacted) hydrogen is now a hydride anion, as it was left with two electrons previously in the H-H sigma bond. Next, the electrons of the negatively charged hydride ion form a bond with the positively charged carbon. This reaction is exothermic. It will occur, but it is very slow without a catalyst.\r\n\r\n<\/div>\r\n<div id=\"section_2\">\r\n<h3 class=\"editable\">The Catalyst<\/h3>\r\nA <a class=\"external\" title=\"http:\/\/en.wikipedia.org\/wiki\/Catalyst\" href=\"http:\/\/en.wikipedia.org\/wiki\/Catalyst\" target=\"_blank\" rel=\"external nofollow noopener\">catalyst<\/a> increases the reaction rate by lowering the activation energy of the reaction. Although the catalyst is not consumed in the reaction, it is required to accelerate the reaction sufficiently to be observed in a reasonable amount of time. Catalysts commonly used in alkene hydrogenation are: platinum, palladium, and nickel. The metal catalyst acts as a surface on which the reaction takes place. This increases the rate by putting the reactants in close proximity to each other, facilitating interactions between them. With this catalyst present, the sigma bond of H<sub>2<\/sub> breaks, and the two hydrogen atoms instead bind to the metal (see #2 in the figure below).\u00a0 The $$\\pi$$ bond of the alkene weakens as it also interacts with the metal (see #3 below).\r\n\r\nSince both the reactants are bound to the metal catalyst, the hydrogen atoms can easily add, one at a time, to the previously double-bonded carbons (see #4 and #5 below). The position of both of the reactants bound to the catalyst makes it so the hydrogen atoms are only exposed to one side of the alkene. This explains why the hydrogen atoms add to same side of the molecule, called syn-addition.\r\n\r\n[caption id=\"\" align=\"aligncenter\" width=\"390\"]<img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135831\/chem1.jpg\" alt=\"chem1.jpg\" width=\"390\" height=\"263\" \/> Figure 1: \u00a0Hydrogenation takes place in the presence of a metal catalyst.[\/caption]\r\n\r\n<div>\r\n<blockquote>\r\n<p class=\"boxtitle\">Note: The catalyst remains intact and unchanged throughout the reaction.<\/p>\r\n<\/blockquote>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_3\">\r\n<h3 class=\"editable\"><strong>Heats of Hydrogenation<\/strong><\/h3>\r\nThe stability of alkene can be determined by measuring the amount of energy associated with the hydrogenation of the molecule.\u00a0 Since the double bond is breaking in this reaction, the energy released in hydrogenation is proportional to the energy in the double bond of the molecule. This is a useful tool because heats of hydrogenation can be measured very accurately. The $$\\Delta H^o$$ is usually around -30 kcal\/mol for alkenes. Stability is simply a measure of energy.\u00a0 Lower energy molecules are more stable than higher energy molecules. More substituted alkenes are more stable than less substituted ones due to <a class=\"external\" title=\"http:\/\/en.wikipedia.org\/wiki\/Hyperconjugation\" href=\"http:\/\/en.wikipedia.org\/wiki\/Hyperconjugation\" target=\"_blank\" rel=\"external nofollow noopener\">hyperconjugation<\/a>. They have a lower heat of hydrogenation.\u00a0 The following illustrates stability of alkenes with various substituents:\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\/05135834\/deigram13.jpg\" alt=\"deigram13.jpg\" width=\"548\" height=\"165\" \/>\r\n\r\nIn disubstituted alkenes, trans isomers are more stable than cis isomers due to <span class=\"external\">steric hindrance<\/span>.\u00a0 Also, internal alkenes are more stable than terminal ones.\u00a0 See the following isomers of butene:\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\/05135836\/butene.jpg\" alt=\"butene.jpg\" width=\"544\" height=\"94\" \/>\r\n\r\n[caption id=\"\" align=\"aligncenter\" width=\"550\"]<img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135838\/image.jpg\" alt=\"image.jpg\" width=\"550\" height=\"525\" \/> Figure 7.6.3: Trans-2-butene is the most stable because it has the lowest heat of hydrogenation.[\/caption]\r\n\r\n<div>\r\n<blockquote>\r\n<p class=\"boxtitle\">Note: In cycloalkenes smaller than cyclooctene, the cis isomers are more stable than the trans as a result of ring strain.<\/p>\r\n<\/blockquote>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_4\">\r\n<h3 class=\"editable\">Outside Links<\/h3>\r\n<ul>\r\n \t<li>Helpful Information:\u00a0 <a class=\"external\" title=\"http:\/\/www.wou.edu\/las\/physci\/ch334\/lecture\/lect16.htm\" href=\"http:\/\/www.wou.edu\/las\/physci\/ch334\/lecture\/lect16.htm\" rel=\"freeklink\">http:\/\/www.wou.edu\/las\/physci\/ch334\/...ure\/lect16.htm<\/a><\/li>\r\n \t<li>Hydrogenation Wikipedia page:\u00a0 <a class=\"external\" title=\"http:\/\/en.wikipedia.org\/wiki\/Hydrogenation\" href=\"http:\/\/en.wikipedia.org\/wiki\/Hydrogenation\" rel=\"freeklink\">http:\/\/en.wikipedia.org\/wiki\/Hydrogenation<\/a><\/li>\r\n \t<li>More professional animation:\u00a0 <a class=\"external\" title=\"http:\/\/www.jbpub.com\/organic-online\/movies\/cathyd.htm\" href=\"http:\/\/www.jbpub.com\/organic-online\/movies\/cathyd.htm\" rel=\"freeklink\">http:\/\/www.jbpub.com\/organic-online\/movies\/cathyd.htm<\/a><\/li>\r\n<\/ul>\r\n<\/div>\r\n<div id=\"section_5\">\r\n<h3 class=\"editable\">References<\/h3>\r\n<ol>\r\n \t<li>Fox, Marye Anne, and James K. Whitesell. <u>Organic Chemistry<\/u>. 3rd ed. Sudbury, MA: Janes and Bartlett Publishers, 2004.<\/li>\r\n \t<li>Hanson, James R. <u>Functional Group Chemistry<\/u>. Bristol, UK: The Royal Society of Chemistry, 2001.<\/li>\r\n \t<li>Streitwieser, Andrew Jr., and Clayton H. Heathcock. <u>Introduction to Organic Chemistry<\/u>. 2nd ed. New York, NY: Macmillan Publishing Co., Inc., 1981.<\/li>\r\n \t<li>Vollhardt, Peter C., and Neil E. Schore. <u>Organic Chemistry: Structure and Function<\/u>. 5th ed. New York, NY: W.H. Freeman and Company, 2007.<\/li>\r\n \t<li>Zlatkis, Albert, Eberhard Breitmaier, and Gunther Jung. <u>A Concise Introduction to Organic Chemistry<\/u>. New York: McGraw-Hill Book Company, 1973.<\/li>\r\n<\/ol>\r\n<\/div>\r\n<div id=\"section_6\">\r\n<div class=\"textbox examples\">\r\n<h3>Examples<\/h3>\r\n<div id=\"section_6\">\r\n<h3 class=\"editable\">Problems and Review Questions<\/h3>\r\n<ol>\r\n \t<li>Bromobutene reacts with hydrogen gas in the presence of a platinum catalyst.\u00a0 What is the name of the product?<\/li>\r\n \t<li>Cyclohexene reacts with hydrogen gas in the presence of a palladium catalyst.\u00a0 What is the name of the product?<\/li>\r\n \t<li>What is the stereochemistry of an alkene hydrogenation reaction?<\/li>\r\n \t<li>When looking at their heats of hydrogenation, is the cis or the trans isomer generally more stable?<\/li>\r\n \t<li>2-chloro-4-ethyl-3methylcyclohexene reacts with hydrogen gas in the presence of a platinum catalyst.\u00a0 What is the name of the product?<\/li>\r\n \t<li>\u00a0\u00a0\u00a0\u00a0<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135841\/prob2.jpg\" alt=\"prob2.jpg\" width=\"261\" height=\"73\" \/><\/li>\r\n<\/ol>\r\n<\/div>\r\n<div id=\"section_7\">\r\n<h3 class=\"editable\">Answers<\/h3>\r\n<ol>\r\n \t<li>[reveal-answer q=\"47136\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"47136\"]Bromobutane[\/hidden-answer]<\/li>\r\n \t<li>[reveal-answer q=\"798592\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"798592\"]Cyclohexane[\/hidden-answer]<\/li>\r\n \t<li>[reveal-answer q=\"38243\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"38243\"]Syn-addition[\/hidden-answer]<\/li>\r\n \t<li>[reveal-answer q=\"966420\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"966420\"]Trans[\/hidden-answer]<\/li>\r\n \t<li>[reveal-answer q=\"992614\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"992614\"]2-chloro-4-ethyl-3methylcyclohexane[\/hidden-answer]<\/li>\r\n \t<li>[reveal-answer q=\"493671\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"493671\"]<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135843\/ans3.jpg\" alt=\"ans3.jpg\" width=\"151\" height=\"98\" \/>[\/hidden-answer]<\/li>\r\n<\/ol>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_8\">\r\n<div class=\"textbox exercises\">\r\n<h3>Exercises<\/h3>\r\n<div id=\"section_8\">\r\n<div id=\"s61712\">\r\n<div id=\"section_20\">\r\n<h3 id=\"Questions-61712\">Question<\/h3>\r\n<strong>1.<\/strong>\r\n\r\nWhich is the more stable alkene in each pair?\r\n\r\n<img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05135846\/7.6.png\" alt=\"\" width=\"547\" height=\"394\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_21\">\r\n<h3 id=\"Solutions-61712\">Solution<\/h3>\r\n[reveal-answer q=\"969394\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"969394\"]A \u2013 2\r\n\r\nB \u2013 1[\/hidden-answer]\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_9\">\r\n<h3 class=\"editable\">Contributors<\/h3>\r\n<ul>\r\n \t<li>Anna Manis (UCD)<\/li>\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<\/ul>\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>explain why cis alkenes are generally less stable than their trans isomers.<\/li>\n<li>explain that catalytic reduction of a cis alkene produces the same alkane as the catalytic reduction of the trans isomer.<\/li>\n<li>explain how heats of hydrogenation (<em>\u0394H<\/em>\u00b0<sub>hydrog<\/sub>) can be used to show that cis alkenes are less stable than their trans isomers, and discuss, briefly, the limitations of this approach.<\/li>\n<li>arrange a series of alkenes in order of increasing or decreasing stability.<\/li>\n<li>describe, briefly, two of the hypotheses proposed to explain why alkene stability increases with increased substitution.<br \/>\n<blockquote><p><strong>Note:<\/strong> This problem is a typical example of those instances in science where there is probably no single \u201ccorrect\u201d explanation for an observed phenomenon.<\/p><\/blockquote>\n<\/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>catalytic hydrogenation<\/li>\n<li>heat of hydrogenation, (<em>\u0394H<\/em>\u00b0<sub>hydrog<\/sub>)<\/li>\n<li>hyperconjugation<\/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 two alkenes,\u00a0<em>cis<\/em>\u00a0<span id=\"MathJax-Element-1-Frame\" class=\"MathJax\" role=\"presentation\"><span id=\"MathJax-Span-1\" class=\"math\"><span id=\"MathJax-Span-2\" class=\"mrow\"><span id=\"MathJax-Span-3\" class=\"texatom\"><span id=\"MathJax-Span-4\" class=\"mrow\"><span id=\"MathJax-Span-5\" class=\"msubsup\"><span id=\"MathJax-Span-6\" class=\"mtext\">\ud835\udda2\ud835\udda7<\/span><span id=\"MathJax-Span-7\" class=\"texatom\"><span id=\"MathJax-Span-8\" class=\"mrow\"><span id=\"MathJax-Span-9\" class=\"mspace\"><\/span><\/span><\/span><span id=\"MathJax-Span-10\" class=\"texatom\"><span id=\"MathJax-Span-11\" class=\"mrow\"><span id=\"MathJax-Span-12\" class=\"mn\">\ud835\udfe5<\/span><\/span><\/span><\/span><span id=\"MathJax-Span-13\" class=\"mtext\">\ud835\udda2\ud835\udda7<\/span><span id=\"MathJax-Span-14\" class=\"texatom\"><span id=\"MathJax-Span-15\" class=\"mrow\"><span id=\"MathJax-Span-16\" class=\"mo\">=<\/span><\/span><\/span><span id=\"MathJax-Span-17\" class=\"msubsup\"><span id=\"MathJax-Span-18\" class=\"mtext\">\ud835\udda2\ud835\udda7\ud835\udda2\ud835\udda7<\/span><span id=\"MathJax-Span-19\" class=\"texatom\"><span id=\"MathJax-Span-20\" class=\"mrow\"><span id=\"MathJax-Span-21\" class=\"mspace\"><\/span><\/span><\/span><span id=\"MathJax-Span-22\" class=\"texatom\"><span id=\"MathJax-Span-23\" class=\"mrow\"><span id=\"MathJax-Span-24\" class=\"mn\">\ud835\udfe5<\/span><\/span><\/span><\/span><\/span><\/span><\/span><\/span><span class=\"MJX_Assistive_MathML\" role=\"presentation\">CH3CH=CHCH3<\/span><\/span>\u00a0and\u00a0<span id=\"MathJax-Element-2-Frame\" class=\"MathJax\" role=\"presentation\"><span id=\"MathJax-Span-25\" class=\"math\"><span id=\"MathJax-Span-26\" class=\"mrow\"><span id=\"MathJax-Span-27\" class=\"texatom\"><span id=\"MathJax-Span-28\" class=\"mrow\"><span id=\"MathJax-Span-29\" class=\"msubsup\"><span id=\"MathJax-Span-30\" class=\"texatom\"><span id=\"MathJax-Span-31\" class=\"mrow\"><span id=\"MathJax-Span-32\" class=\"mo\">(<\/span><span id=\"MathJax-Span-33\" class=\"msubsup\"><span id=\"MathJax-Span-34\" class=\"mtext\">\ud835\udda2\ud835\udda7<\/span><span id=\"MathJax-Span-35\" class=\"texatom\"><span id=\"MathJax-Span-36\" class=\"mrow\"><span id=\"MathJax-Span-37\" class=\"mspace\"><\/span><\/span><\/span><span id=\"MathJax-Span-38\" class=\"texatom\"><span id=\"MathJax-Span-39\" class=\"mrow\"><span id=\"MathJax-Span-40\" class=\"mn\">\ud835\udfe5<\/span><\/span><\/span><\/span><span id=\"MathJax-Span-41\" class=\"mo\">)<\/span><\/span><\/span><span id=\"MathJax-Span-42\" class=\"texatom\"><span id=\"MathJax-Span-43\" class=\"mrow\"><span id=\"MathJax-Span-44\" class=\"mspace\"><\/span><\/span><\/span><span id=\"MathJax-Span-45\" class=\"texatom\"><span id=\"MathJax-Span-46\" class=\"mrow\"><span id=\"MathJax-Span-47\" class=\"mn\">\ud835\udfe4<\/span><\/span><\/span><\/span><span id=\"MathJax-Span-48\" class=\"mtext\">\ud835\udda2<\/span><span id=\"MathJax-Span-49\" class=\"texatom\"><span id=\"MathJax-Span-50\" class=\"mrow\"><span id=\"MathJax-Span-51\" class=\"mo\">=<\/span><\/span><\/span><span id=\"MathJax-Span-52\" class=\"msubsup\"><span id=\"MathJax-Span-53\" class=\"mtext\">\ud835\udda2\ud835\udda7<\/span><span id=\"MathJax-Span-54\" class=\"texatom\"><span id=\"MathJax-Span-55\" class=\"mrow\"><span id=\"MathJax-Span-56\" class=\"mspace\"><\/span><\/span><\/span><span id=\"MathJax-Span-57\" class=\"texatom\"><span id=\"MathJax-Span-58\" class=\"mrow\"><span id=\"MathJax-Span-59\" class=\"mn\">\ud835\udfe4<\/span><\/span><\/span><\/span><\/span><\/span><\/span><\/span><span class=\"MJX_Assistive_MathML\" role=\"presentation\">(CH3)2C=CH2<\/span><\/span>\u00a0have similar heats of hydrogenation (\u2212120 kJ\/mol and \u2212119 kJ\/mol, respectively), and are therefore of similar stability. However, they are both less stable than\u00a0<em>trans<\/em>\u00a0<span id=\"MathJax-Element-3-Frame\" class=\"MathJax\" role=\"presentation\"><span id=\"MathJax-Span-60\" class=\"math\"><span id=\"MathJax-Span-61\" class=\"mrow\"><span id=\"MathJax-Span-62\" class=\"texatom\"><span id=\"MathJax-Span-63\" class=\"mrow\"><span id=\"MathJax-Span-64\" class=\"msubsup\"><span id=\"MathJax-Span-65\" class=\"mtext\">\ud835\udda2\ud835\udda7<\/span><span id=\"MathJax-Span-66\" class=\"texatom\"><span id=\"MathJax-Span-67\" class=\"mrow\"><span id=\"MathJax-Span-68\" class=\"mspace\"><\/span><\/span><\/span><span id=\"MathJax-Span-69\" class=\"texatom\"><span id=\"MathJax-Span-70\" class=\"mrow\"><span id=\"MathJax-Span-71\" class=\"mn\">\ud835\udfe5<\/span><\/span><\/span><\/span><span id=\"MathJax-Span-72\" class=\"mtext\">\ud835\udda2\ud835\udda7<\/span><span id=\"MathJax-Span-73\" class=\"texatom\"><span id=\"MathJax-Span-74\" class=\"mrow\"><span id=\"MathJax-Span-75\" class=\"mo\">=<\/span><\/span><\/span><span id=\"MathJax-Span-76\" class=\"msubsup\"><span id=\"MathJax-Span-77\" class=\"mtext\">\ud835\udda2\ud835\udda7\ud835\udda2\ud835\udda7<\/span><span id=\"MathJax-Span-78\" class=\"texatom\"><span id=\"MathJax-Span-79\" class=\"mrow\"><span id=\"MathJax-Span-80\" class=\"mspace\"><\/span><\/span><\/span><span id=\"MathJax-Span-81\" class=\"texatom\"><span id=\"MathJax-Span-82\" class=\"mrow\"><span id=\"MathJax-Span-83\" class=\"mn\">\ud835\udfe5<\/span><\/span><\/span><\/span><\/span><\/span><\/span><\/span><span class=\"MJX_Assistive_MathML\" role=\"presentation\">CH3CH=CHCH3<\/span><\/span>\u00a0(\u2212116 kJ\/mol).<\/p>\n<p>You may wonder why an <em>sp<\/em><sup>2<\/sup>\u00a0&#8211;<em>sp<\/em><sup>3<\/sup> bond is stronger than an sp<sup>3<\/sup>-sp<sup>3<\/sup> bond. Bond strength depends on the efficiency with which orbitals can overlap. In general, <em>s<\/em>\u00a0orbitals overlap more efficiently than do <em>p<\/em>\u00a0orbitals; therefore, the <em>s<\/em>&#8211;<em>s<\/em> bond in the hydrogen molecule is stronger than the <em>p<\/em>&#8211;<em>p<\/em> bond in fluorine. In hybrid orbitals, the greater the <em>s<\/em> character of the orbital, the more efficiently it can overlap: an <em>sp<\/em><sup>2<\/sup> orbital, which has a 33% <em>s<\/em> character, can overlap more effectively than an <em>sp<\/em><sup>3<\/sup> orbital, with only 25% <em>s<\/em> character.<\/p>\n<\/div>\n<\/div>\n<p>Alkene hydrogenation is the <span class=\"external\">syn-addition<\/span> of hydrogen to an <a title=\"Organic Chemistry\/Hydrocarbons\/Alkenes\" href=\"https:\/\/chem.libretexts.org\/Core\/Organic_Chemistry\/Hydrocarbons\/Alkenes\" rel=\"internal\"><span class=\"external\">alkene<\/span><\/a>, saturating the bond.\u00a0 The alkene reacts with hydrogen gas in the presence of a metal catalyst which allows the reaction to occur quickly. The energy released in this process, called the heat of <span class=\"external\">hydrogenation<\/span>,\u00a0 indicates the relative stability of the double bond in the molecule (see <a title=\"Organic Chemistry\/Hydrocarbons\/Alkenes\/Catalytic Hydrogenation\" rel=\"broken\"><span class=\"external\">Catalytic Hydrogenation<\/span><\/a>).<\/p>\n<div id=\"section_1\">\n<h3 class=\"editable\">Introduction<\/h3>\n<p>The reaction begins with H<sub>2<\/sub> gas and an alkene (a carbon-carbon double bond). The <span class=\"external\">pi bond<\/span> in the alkene acts as a nucleophile; the two electrons in it form a sigma bond with one of the hydrogen atoms in H<sub>2<\/sub>. With the pi bond broken, the other carbon (the one that did not newly receive a hydrogen) is left with a positive formal charge. This is the carbocation intermediate. The remaining (unreacted) hydrogen is now a hydride anion, as it was left with two electrons previously in the H-H sigma bond. Next, the electrons of the negatively charged hydride ion form a bond with the positively charged carbon. This reaction is exothermic. It will occur, but it is very slow without a catalyst.<\/p>\n<\/div>\n<div id=\"section_2\">\n<h3 class=\"editable\">The Catalyst<\/h3>\n<p>A <a class=\"external\" title=\"http:\/\/en.wikipedia.org\/wiki\/Catalyst\" href=\"http:\/\/en.wikipedia.org\/wiki\/Catalyst\" target=\"_blank\" rel=\"external nofollow noopener\">catalyst<\/a> increases the reaction rate by lowering the activation energy of the reaction. Although the catalyst is not consumed in the reaction, it is required to accelerate the reaction sufficiently to be observed in a reasonable amount of time. Catalysts commonly used in alkene hydrogenation are: platinum, palladium, and nickel. The metal catalyst acts as a surface on which the reaction takes place. This increases the rate by putting the reactants in close proximity to each other, facilitating interactions between them. With this catalyst present, the sigma bond of H<sub>2<\/sub> breaks, and the two hydrogen atoms instead bind to the metal (see #2 in the figure below).\u00a0 The $$\\pi$$ bond of the alkene weakens as it also interacts with the metal (see #3 below).<\/p>\n<p>Since both the reactants are bound to the metal catalyst, the hydrogen atoms can easily add, one at a time, to the previously double-bonded carbons (see #4 and #5 below). The position of both of the reactants bound to the catalyst makes it so the hydrogen atoms are only exposed to one side of the alkene. This explains why the hydrogen atoms add to same side of the molecule, called syn-addition.<\/p>\n<div style=\"width: 400px\" 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\/05135831\/chem1.jpg\" alt=\"chem1.jpg\" width=\"390\" height=\"263\" \/><\/p>\n<p class=\"wp-caption-text\">Figure 1: \u00a0Hydrogenation takes place in the presence of a metal catalyst.<\/p>\n<\/div>\n<div>\n<blockquote>\n<p class=\"boxtitle\">Note: The catalyst remains intact and unchanged throughout the reaction.<\/p>\n<\/blockquote>\n<\/div>\n<\/div>\n<div id=\"section_3\">\n<h3 class=\"editable\"><strong>Heats of Hydrogenation<\/strong><\/h3>\n<p>The stability of alkene can be determined by measuring the amount of energy associated with the hydrogenation of the molecule.\u00a0 Since the double bond is breaking in this reaction, the energy released in hydrogenation is proportional to the energy in the double bond of the molecule. This is a useful tool because heats of hydrogenation can be measured very accurately. The $$\\Delta H^o$$ is usually around -30 kcal\/mol for alkenes. Stability is simply a measure of energy.\u00a0 Lower energy molecules are more stable than higher energy molecules. More substituted alkenes are more stable than less substituted ones due to <a class=\"external\" title=\"http:\/\/en.wikipedia.org\/wiki\/Hyperconjugation\" href=\"http:\/\/en.wikipedia.org\/wiki\/Hyperconjugation\" target=\"_blank\" rel=\"external nofollow noopener\">hyperconjugation<\/a>. They have a lower heat of hydrogenation.\u00a0 The following illustrates stability of alkenes with various substituents:<\/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\/05135834\/deigram13.jpg\" alt=\"deigram13.jpg\" width=\"548\" height=\"165\" \/><\/p>\n<p>In disubstituted alkenes, trans isomers are more stable than cis isomers due to <span class=\"external\">steric hindrance<\/span>.\u00a0 Also, internal alkenes are more stable than terminal ones.\u00a0 See the following isomers of butene:<\/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\/05135836\/butene.jpg\" alt=\"butene.jpg\" width=\"544\" height=\"94\" \/><\/p>\n<div style=\"width: 560px\" 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\/05135838\/image.jpg\" alt=\"image.jpg\" width=\"550\" height=\"525\" \/><\/p>\n<p class=\"wp-caption-text\">Figure 7.6.3: Trans-2-butene is the most stable because it has the lowest heat of hydrogenation.<\/p>\n<\/div>\n<div>\n<blockquote>\n<p class=\"boxtitle\">Note: In cycloalkenes smaller than cyclooctene, the cis isomers are more stable than the trans as a result of ring strain.<\/p>\n<\/blockquote>\n<\/div>\n<\/div>\n<div id=\"section_4\">\n<h3 class=\"editable\">Outside Links<\/h3>\n<ul>\n<li>Helpful Information:\u00a0 <a class=\"external\" title=\"http:\/\/www.wou.edu\/las\/physci\/ch334\/lecture\/lect16.htm\" href=\"http:\/\/www.wou.edu\/las\/physci\/ch334\/lecture\/lect16.htm\" rel=\"freeklink\">http:\/\/www.wou.edu\/las\/physci\/ch334\/&#8230;ure\/lect16.htm<\/a><\/li>\n<li>Hydrogenation Wikipedia page:\u00a0 <a class=\"external\" title=\"http:\/\/en.wikipedia.org\/wiki\/Hydrogenation\" href=\"http:\/\/en.wikipedia.org\/wiki\/Hydrogenation\" rel=\"freeklink\">http:\/\/en.wikipedia.org\/wiki\/Hydrogenation<\/a><\/li>\n<li>More professional animation:\u00a0 <a class=\"external\" title=\"http:\/\/www.jbpub.com\/organic-online\/movies\/cathyd.htm\" href=\"http:\/\/www.jbpub.com\/organic-online\/movies\/cathyd.htm\" rel=\"freeklink\">http:\/\/www.jbpub.com\/organic-online\/movies\/cathyd.htm<\/a><\/li>\n<\/ul>\n<\/div>\n<div id=\"section_5\">\n<h3 class=\"editable\">References<\/h3>\n<ol>\n<li>Fox, Marye Anne, and James K. Whitesell. <u>Organic Chemistry<\/u>. 3rd ed. Sudbury, MA: Janes and Bartlett Publishers, 2004.<\/li>\n<li>Hanson, James R. <u>Functional Group Chemistry<\/u>. Bristol, UK: The Royal Society of Chemistry, 2001.<\/li>\n<li>Streitwieser, Andrew Jr., and Clayton H. Heathcock. <u>Introduction to Organic Chemistry<\/u>. 2nd ed. New York, NY: Macmillan Publishing Co., Inc., 1981.<\/li>\n<li>Vollhardt, Peter C., and Neil E. Schore. <u>Organic Chemistry: Structure and Function<\/u>. 5th ed. New York, NY: W.H. Freeman and Company, 2007.<\/li>\n<li>Zlatkis, Albert, Eberhard Breitmaier, and Gunther Jung. <u>A Concise Introduction to Organic Chemistry<\/u>. New York: McGraw-Hill Book Company, 1973.<\/li>\n<\/ol>\n<\/div>\n<div id=\"section_6\">\n<div class=\"textbox examples\">\n<h3>Examples<\/h3>\n<div id=\"section_6\">\n<h3 class=\"editable\">Problems and Review Questions<\/h3>\n<ol>\n<li>Bromobutene reacts with hydrogen gas in the presence of a platinum catalyst.\u00a0 What is the name of the product?<\/li>\n<li>Cyclohexene reacts with hydrogen gas in the presence of a palladium catalyst.\u00a0 What is the name of the product?<\/li>\n<li>What is the stereochemistry of an alkene hydrogenation reaction?<\/li>\n<li>When looking at their heats of hydrogenation, is the cis or the trans isomer generally more stable?<\/li>\n<li>2-chloro-4-ethyl-3methylcyclohexene reacts with hydrogen gas in the presence of a platinum catalyst.\u00a0 What is the name of the product?<\/li>\n<li>\u00a0\u00a0\u00a0\u00a0<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\/05135841\/prob2.jpg\" alt=\"prob2.jpg\" width=\"261\" height=\"73\" \/><\/li>\n<\/ol>\n<\/div>\n<div id=\"section_7\">\n<h3 class=\"editable\">Answers<\/h3>\n<ol>\n<li>\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q47136\">Show Answer<\/span><\/p>\n<div id=\"q47136\" class=\"hidden-answer\" style=\"display: none\">Bromobutane<\/div>\n<\/div>\n<\/li>\n<li>\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q798592\">Show Answer<\/span><\/p>\n<div id=\"q798592\" class=\"hidden-answer\" style=\"display: none\">Cyclohexane<\/div>\n<\/div>\n<\/li>\n<li>\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q38243\">Show Answer<\/span><\/p>\n<div id=\"q38243\" class=\"hidden-answer\" style=\"display: none\">Syn-addition<\/div>\n<\/div>\n<\/li>\n<li>\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q966420\">Show Answer<\/span><\/p>\n<div id=\"q966420\" class=\"hidden-answer\" style=\"display: none\">Trans<\/div>\n<\/div>\n<\/li>\n<li>\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q992614\">Show Answer<\/span><\/p>\n<div id=\"q992614\" class=\"hidden-answer\" style=\"display: none\">2-chloro-4-ethyl-3methylcyclohexane<\/div>\n<\/div>\n<\/li>\n<li>\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q493671\">Show Answer<\/span><\/p>\n<div id=\"q493671\" class=\"hidden-answer\" style=\"display: none\"><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\/05135843\/ans3.jpg\" alt=\"ans3.jpg\" width=\"151\" height=\"98\" \/><\/div>\n<\/div>\n<\/li>\n<\/ol>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_8\">\n<div class=\"textbox exercises\">\n<h3>Exercises<\/h3>\n<div id=\"section_8\">\n<div id=\"s61712\">\n<div id=\"section_20\">\n<h3 id=\"Questions-61712\">Question<\/h3>\n<p><strong>1.<\/strong><\/p>\n<p>Which is the more stable alkene in each pair?<\/p>\n<p><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\/05135846\/7.6.png\" alt=\"\" width=\"547\" height=\"394\" \/><\/p>\n<\/div>\n<div id=\"section_21\">\n<h3 id=\"Solutions-61712\">Solution<\/h3>\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q969394\">Show Answer<\/span><\/p>\n<div id=\"q969394\" class=\"hidden-answer\" style=\"display: none\">A \u2013 2<\/p>\n<p>B \u2013 1<\/p><\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_9\">\n<h3 class=\"editable\">Contributors<\/h3>\n<ul>\n<li>Anna Manis (UCD)<\/li>\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<\/ul>\n<\/div>\n<\/div>\n","protected":false},"author":44985,"menu_order":7,"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-1006","chapter","type-chapter","status-publish","hentry"],"part":23,"_links":{"self":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/1006","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":6,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/1006\/revisions"}],"predecessor-version":[{"id":2284,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/1006\/revisions\/2284"}],"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\/1006\/metadata\/"}],"wp:attachment":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/media?parent=1006"}],"wp:term":[{"taxonomy":"chapter-type","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapter-type?post=1006"},{"taxonomy":"contributor","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/contributor?post=1006"},{"taxonomy":"license","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/license?post=1006"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}