{"id":1085,"date":"2017-10-19T14:05:45","date_gmt":"2017-10-19T14:05:45","guid":{"rendered":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/?post_type=chapter&#038;p=1085"},"modified":"2018-10-03T20:56:23","modified_gmt":"2018-10-03T20:56:23","slug":"hydration-of-alkenes-hydroboration","status":"publish","type":"chapter","link":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/chapter\/hydration-of-alkenes-hydroboration\/","title":{"raw":"Hydration of Alkenes: Hydroboration","rendered":"Hydration of Alkenes: Hydroboration"},"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>identify hydroboration (followed by oxidation) as a method for bringing about the (apparently) non-Markovnikov addition of water to an alkene.<\/li>\r\n \t<li>write an equation for the formation of a trialkylborane from an alkene and borane.<\/li>\r\n \t<li>write an equation for the oxidation of a trialkylborane to an alcohol.<\/li>\r\n \t<li>draw the structure of the alcohol produced by the hydroboration, and subsequent oxidation, of a given alkene.<\/li>\r\n \t<li>determine whether a given alcohol should be prepared by oxymercuration-demercuration or by hydroboration-oxidation, and identify the alkene and reagents required to carry out such a synthesis.<\/li>\r\n \t<li>write the detailed mechanism for the addition of borane to an alkene, and explain the stereochemistry and regiochemistry of the reaction.<\/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 class=\"boxtitle\">Key Terms<\/h3>\r\nMake certain that you can define, and use in context, the key term below.\r\n<ul>\r\n \t<li>hydroboration<\/li>\r\n<\/ul>\r\n<\/div>\r\n<div class=\"textbox\">\r\n<div><\/div>\r\n<div id=\"note\">\r\n<h3 class=\"boxtitle\">Study Notes<\/h3>\r\nThe two most important factors influencing organic reactions are polar (or electronic) effects and steric effects.\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\nHydroboration-Oxidation is a two step pathway used\u00a0to produce\u00a0alcohols. The reaction proceeds in an <a class=\"internal\" title=\"Wikitexts\/UCD Chem 118B\/Chem 118B Topics\/Radical Additions--Anti-Markovnikov Product Formation\" href=\"\/Organic_Chemistry\/Hydrocarbons\/Alkenes\/Reactions_of_Alkenes\/Radical_Additions--Anti-Markovnikov_Product_Formation\" rel=\"internal\">Anti-Markovnikov<\/a> manner, where the\u00a0hydrogen (from BH<sub>3<\/sub> or BHR<sub>2<\/sub>) attaches to the more substituted carbon and the boron\u00a0attaches to the\u00a0least substituted carbon in the <a class=\"internal\" title=\"Organic Chemistry\/Hydrocarbons\/Alkenes\" href=\"\/Organic_Chemistry\/Hydrocarbons\/Alkenes\" rel=\"internal\">alkene<\/a> bouble bond. Furthermore, the borane acts as a lewis acid by\u00a0accepting two electrons in its empty p\u00a0orbital\u00a0from\u00a0an alkene that is electron rich. This process allows boron to have\u00a0an electron octet.\u00a0 A very interesting characteristic of this process is that it does not require any activation\u00a0by a catalyst.\u00a0The Hydroboration mechanism\u00a0has\u00a0the elements of both hydrogenation and <a class=\"internal\" title=\"Wikitexts\/UCD Chem 118B\/Chem 118B Topics\/Electrophilic Attack on Conjugated Dienes\/Electrophile\" href=\"\/Organic_Chemistry\/Conjugation\/Electrophilic_Attack_on_Conjugated_Dienes\/Electrophile\" rel=\"internal\">electrophilic<\/a> addition\u00a0and it is\u00a0a stereospecific\u00a0(<strong><em>syn addition),<\/em><\/strong> meaning that the\u00a0hydroboration takes place on the same\u00a0face of the double bond, this leads <em><strong>cis<\/strong><\/em> stereochemistry.\r\n<div>\r\n<div id=\"section_1\">\r\n<h3 class=\"editable\">Introduction<\/h3>\r\nHydroboration-oxidation of alkenes has been a very valuable laboratory method for the stereoselectivity and regioselectivity of alkenes. An Additional feature of this reaction is that it occurs without rearrangement.\r\n\r\n<\/div>\r\n<\/div>\r\n<div>\r\n<div id=\"section_2\">\r\n<h3 class=\"editable\">The Borane Complex<\/h3>\r\nFirst off it is very imporatnt to understand\u00a0little bit\u00a0about the structure and the properties of the borane molecule. Borane exists naturally as a very toxic gas and it exists as dimer of the general formula B<sub>2<\/sub>H<sub>6<\/sub> (diborane). Additionally, the dimer B<sub>2<\/sub>H<sub>6<\/sub>ignites spontaneously in air. Borane is commercially available in ether and tetrahydrofuran (THF), in these solutions the borane can exist as a lewis acid-base complex, which allows boron to have an electron octet.BH3\u2192B2H6\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/2058\/THF.bmp?revision=1&amp;size=bestfit&amp;width=451&amp;height=122#fixme\" alt=\"THF.bmp\" width=\"451px\" height=\"122px\" \/>\r\n\r\n<\/div>\r\n<\/div>\r\n<div>\r\n<div id=\"section_3\">\r\n<h3 class=\"editable\">The Mechanism<\/h3>\r\n<div class=\"editIcon\"><\/div>\r\n<div>\r\n<div id=\"section_4\">\r\n<h4 class=\"editable\"><strong>Step #1<\/strong><\/h4>\r\n<ul>\r\n \t<li>Part #1: Hydroboration of the alkene. In this first step the addittion of the borane to the alkene is initiated and prceeds as a concerted reaction because bond breaking and bond formation occurs at the same time. This part consists of the vacant 2p orbital of the boron electrophile pairing with the electron pair of the ? bondof the nucleophile.<\/li>\r\n<\/ul>\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/2049\/concerted_reaction_1.bmp?revision=1&amp;size=bestfit&amp;width=260&amp;height=191#fixme\" alt=\"concerted reaction 1.bmp\" width=\"260px\" height=\"191px\" \/>\r\n\r\n<strong>Transition state<\/strong>\r\n\r\n<strong><img class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/2059\/TRANSITION_STATE_FINAL_2_(2).bmp?revision=1&amp;size=bestfit&amp;width=441&amp;height=242#fixme\" alt=\"TRANSITION STATE FINAL 2 (2).bmp\" width=\"441px\" height=\"242px\" \/><\/strong>\r\n\r\n<strong>* Note that a carbocation is not formed. Therefore, no rearrangement takes place<\/strong>.\r\n<ul>\r\n \t<li>Part #2: The Anti Markovnikov addition of Boron. The boron adds to the less substituted carbon of the alkene, which then places the hydrogen on the more substituted carbon. Both, the boron and the hydrogen add simultaneously on the same face of the double bond (syn addition).<\/li>\r\n<\/ul>\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05142202\/borination_step_2.gif\" alt=\"borination step 2.gif\" width=\"226\" height=\"79\" \/>\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div>\r\n<div id=\"section_5\">\r\n<h3 class=\"editable\">Oxidation of the Trialkylborane by Hydrogen Peroxide<\/h3>\r\n<div>\r\n<div id=\"section_6\">\r\n<h4 class=\"editable\">Step #2<\/h4>\r\n<ul>\r\n \t<li>Part #1: the first part of this mechanism deals with the donation of a pair of electrons from the hydrogen peroxide ion. the hydrogen peroxide is the nucleophile in this reaction because it is the electron donor to the newly formed trialkylborane that resulted from hydroboration.<\/li>\r\n<\/ul>\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/2052\/peorxide_1.bmp?revision=1&amp;size=bestfit&amp;width=582&amp;height=57#fixme\" alt=\"peorxide 1.bmp\" width=\"582px\" height=\"57px\" \/>\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/2051\/oxidation_part_1_(1).bmp?revision=1&amp;size=bestfit&amp;width=696&amp;height=239#fixme\" alt=\"oxidation part 1 (1).bmp\" width=\"696px\" height=\"239px\" \/>\r\n<ul>\r\n \t<li>Part 2: In this second part of the mechanism, a rearrangement of an R group with its pair of bonding electrons to an adjacent oxygen results in the removal of a hydroxide ion.<\/li>\r\n<\/ul>\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/2042\/1%252C2%252C_SHIFT.bmp?revision=1&amp;size=bestfit&amp;width=655&amp;height=172#fixme\" alt=\"1,2, SHIFT.bmp\" width=\"655px\" height=\"172px\" \/>\r\n\r\n<strong>Two more of these reactions with hydroperoxide will occur in order give a trialkylborate<\/strong>\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/2060\/trialkylborate.bmp?revision=1#fixme\" alt=\"trialkylborate.bmp\" width=\"515\" height=\"168\" \/>\r\n<ul>\r\n \t<li>Part 3: This is the final part of the Oxidation process. In this part the trialkylborate reacts with aqueous NaOH to give the alcohol and sodium borate.<\/li>\r\n<\/ul>\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/2057\/Sodium_Borate.bmp?revision=1&amp;size=bestfit&amp;width=668&amp;height=60#fixme\" alt=\"Sodium Borate.bmp\" width=\"668px\" height=\"60px\" \/>\r\n\r\nIf you need additional visuals to aid you in understanding the mechanism, click on the outside links provided here that will take you to other pages and media that are very helpful as well.\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div>\r\n<div id=\"section_7\">\r\n<h3 class=\"editable\">Stereochemistry of hydroboration<\/h3>\r\nThe hydroboration reaction is among the few simple addition reactions that proceed cleanly in a <em>syn <\/em>fashion. As noted above, this is a single-step reaction. Since the bonding of the double bond carbons to boron and hydrogen is concerted, it follows that the geometry of this addition must be syn. Furthermore, rearrangements are unlikely inasmuch as a discrete carbocation intermediate is never formed. These features are illustrated for the hydroboration of \u03b1-pinene.\r\n\r\n<img class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05142204\/pinene3.gif\" alt=\"image\" \/>\r\n\r\nSince the hydroboration procedure is most commonly used to hydrate alkenes in an anti-Markovnikov fashion, we also need to know the stereoselectivity of the second oxidation reaction, which substitutes a hydroxyl group for the boron atom. Independent study has shown this reaction takes place with retention of configuration so the overall addition of water is also syn.\r\n\r\nThe hydroboration of \u03b1-pinene also provides a nice example of steric hindrance control in a chemical reaction. In the less complex alkenes used in earlier examples the plane of the double bond was often a plane of symmetry, and addition reagents could approach with equal ease from either side. In this case, one of the methyl groups bonded to C-6 (colored blue in the equation) covers one face of the double bond, blocking any approach from that side. All reagents that add to this double bond must therefore approach from the side opposite this methyl.\r\n\r\n<\/div>\r\n<div id=\"section_8\">\r\n<h3 class=\"editable\">Outside links<\/h3>\r\n<ul>\r\n \t<li><a class=\"external\" title=\"http:\/\/en.wikipedia.org\/wiki\/Hydroboration-oxidation\" href=\"http:\/\/en.wikipedia.org\/wiki\/Hydroboration-oxidation\" target=\"_blank\" rel=\"external nofollow noopener\">http:\/\/en.wikipedia.org\/wiki\/Hydroboration-oxidation<\/a><\/li>\r\n \t<li><a class=\"external\" title=\"http:\/\/bcs.whfreeman.com\/vollhardtschore4e\/cat_010\/ch12\/12010-03.htm\" href=\"http:\/\/bcs.whfreeman.com\/vollhardtschore4e\/cat_010\/ch12\/12010-03.htm\" target=\"_blank\" rel=\"external nofollow noopener\">http:\/\/bcs.whfreeman.com\/vollhardtschore4e\/cat_010\/ch12\/12010-03.htm<\/a><\/li>\r\n \t<li><a class=\"external\" title=\"http:\/\/www.chemhelper.com\/hydroboration.html\" href=\"http:\/\/www.chemhelper.com\/hydroboration.html\" target=\"_blank\" rel=\"external nofollow noopener\">http:\/\/www.chemhelper.com\/hydroboration.html<\/a><\/li>\r\n \t<li><a class=\"external\" title=\"http:\/\/www.cartage.org.lb\/en\/themes\/sciences\/chemistry\/Organicchemistry\/CommonReactio\/Hydroboration\/Hydroboration.htm\" href=\"http:\/\/www.cartage.org.lb\/en\/themes\/sciences\/chemistry\/Organicchemistry\/CommonReactio\/Hydroboration\/Hydroboration.htm\" target=\"_blank\" rel=\"external nofollow noopener\">http:\/\/www.cartage.org.lb\/en\/themes\/...roboration.htm<\/a><\/li>\r\n \t<li><a class=\"external\" title=\"http:\/\/www.organic-chemistry.org\/namedreactions\/brown-hydroboration.shtm\" href=\"http:\/\/www.organic-chemistry.org\/namedreactions\/brown-hydroboration.shtm\" target=\"_blank\" rel=\"external nofollow noopener\">http:\/\/www.organic-chemistry.org\/nam...oboration.shtm<\/a><\/li>\r\n<\/ul>\r\n<\/div>\r\n<\/div>\r\n<div>\r\n<div id=\"section_9\">\r\n<h3 class=\"editable\">References<\/h3>\r\n<ol>\r\n \t<li>Vollhardt, Peter, and Neil Shore.\u00a0<u>Organic Chemistry: Structure and Function<\/u>. 5th. New York: W.H. Freeman and Company, 2007.<\/li>\r\n \t<li>Foote, S. Christopher, and William H. Brown. <u>Organic Chemistry<\/u>. 5th. Belmont, CA: Brooks\/Cole Cengage Learning, 2005.<\/li>\r\n \t<li>Bruice, Paula Yurkanis. <u>Oragnic Chemistry<\/u>. 5th. CA. Prentice Hall, 2006.<\/li>\r\n \t<li>Bergbreiter E. David , and David P. Rainville. <u>Stereochemistry of hydroboration-oxidation of terminal alkenes.<\/u>\u00a0<cite>J. Org. Chem.<\/cite>, <span class=\"citation_year\">1976<\/span>, <span class=\"citation_volume\">41<\/span> (18), pp 3031\u20133033<\/li>\r\n \t<li>Ilich, Predrag-Peter; Rickertsen, Lucas S., and Becker Erienne. <u>Polar Addition to C=C Group: Why Is Anti-Markovnikov Hydroboration-Oxidation of Alkenes Not \"Anti-\"?<\/u> Journal of Chemical Education., 2006, v83, n11, pg 1681-1685<\/li>\r\n<\/ol>\r\n<\/div>\r\n<\/div>\r\n<div>\r\n<div id=\"section_10\">\r\n<div class=\"textbox examples\">\r\n<h3>Examples<\/h3>\r\n<div>\r\n<div id=\"section_10\">\r\n<h3 class=\"editable\">Problems<\/h3>\r\n<strong>What are the products of these following reactions? <\/strong>\r\n\r\n<strong>#1.\u00a0<\/strong>\r\n\r\n<strong><img class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/2055\/PROBLEM_1.bmp?revision=1&amp;size=bestfit&amp;width=167&amp;height=84#fixme\" alt=\"PROBLEM 1.bmp\" width=\"167px\" height=\"84px\" \/><\/strong>\r\n\r\n<strong>#2.<\/strong>\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/2054\/PROBLEM_%25232.bmp?revision=1&amp;size=bestfit&amp;width=308&amp;height=91#fixme\" alt=\"PROBLEM #2.bmp\" width=\"308px\" height=\"91px\" \/>\r\n\r\n<strong>#3.<\/strong>\r\n\r\n<strong><img class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/2053\/PROBELM_%25233.bmp?revision=1&amp;size=bestfit&amp;width=445&amp;height=121#fixme\" alt=\"PROBELM #3.bmp\" width=\"445px\" height=\"121px\" \/><\/strong>\r\n\r\n<strong>Draw the structural formulas for the alcohols that result from \u00a0hydroboration-oxidation of the alkenes shown.<\/strong>\r\n\r\n<strong>#4.<\/strong>\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/2056\/problem_4.bmp?revision=1&amp;size=bestfit&amp;width=132&amp;height=80#fixme\" alt=\"problem 4.bmp\" width=\"132px\" height=\"80px\" \/>\r\n\r\n<strong>#5. (E)-3-methyl-2-pentene\u00a0 <\/strong>\r\n\r\nIf you need clarification or a reminder on the nomenclature of alkenes refer to the link below on naming the <a class=\"internal\" title=\"Organic Chemistry\/Hydrocarbons\/Alkenes\" href=\"\/Organic_Chemistry\/Hydrocarbons\/Alkenes\" rel=\"internal\">alkenes.<\/a>\r\n\r\n<\/div>\r\n<\/div>\r\n<div>\r\n<div id=\"section_11\">\r\n<h3 class=\"editable\"><strong>Answers<\/strong><\/h3>\r\n<div class=\"editIcon\">[reveal-answer q=\"760849\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"760849\"]#1.<img class=\"internal default alignnone\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/2043\/answer_%25231.bmp?revision=1&amp;size=bestfit&amp;width=111&amp;height=83#fixme\" alt=\"answer #1.bmp\" width=\"111px\" height=\"83px\" \/>#2.<img class=\"internal default alignnone\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05142206\/hydrobor_prob2_soln.png\" alt=\"hydrobor prob2 soln.png\" width=\"121\" height=\"78\" \/>#3.<img class=\"internal default alignnone\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/2044\/Answer_%25233.bmp?revision=1&amp;size=bestfit&amp;width=245&amp;height=151#fixme\" alt=\"Answer #3.bmp\" width=\"245px\" height=\"151px\" \/>#4.<img class=\"internal default alignnone\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/2045\/ANSWER_%25234.bmp?revision=1&amp;size=bestfit&amp;width=153&amp;height=113#fixme\" alt=\"ANSWER #4.bmp\" width=\"153px\" height=\"113px\" \/>#5.<img class=\"internal default alignnone\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/2046\/Answer_5.bmp?revision=1&amp;size=bestfit&amp;width=183&amp;height=98#fixme\" alt=\"Answer 5.bmp\" width=\"183px\" height=\"98px\" \/>[\/hidden-answer]<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_12\"><\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_12\">\r\n<div class=\"textbox exercises\">\r\n<h3 class=\"editable\">Exercises<\/h3>\r\n<div id=\"section_13\">\r\n<h4 class=\"editable\">Question<\/h4>\r\n<ol>\r\n \t<li>Write out the reagents or products (A\u2013D) shown in the following reaction schemes.<\/li>\r\n<\/ol>\r\n<img class=\"aligncenter\" src=\"http:\/\/chem.libretexts.org\/@api\/deki\/files\/84939\/8-5exercise.png?origin=mt-web\" alt=\"alkene hydration reaction questions\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_14\">\r\n<h3 class=\"editable\">Solution<\/h3>\r\n[reveal-answer q=\"466385\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"466385\"]\r\n\r\n<img class=\"aligncenter\" src=\"http:\/\/chem.libretexts.org\/@api\/deki\/files\/84936\/8-5answer.png?origin=mt-web\" alt=\"alkene hydration reaction answers\" \/>[\/hidden-answer]\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_15\">\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>","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>identify hydroboration (followed by oxidation) as a method for bringing about the (apparently) non-Markovnikov addition of water to an alkene.<\/li>\n<li>write an equation for the formation of a trialkylborane from an alkene and borane.<\/li>\n<li>write an equation for the oxidation of a trialkylborane to an alcohol.<\/li>\n<li>draw the structure of the alcohol produced by the hydroboration, and subsequent oxidation, of a given alkene.<\/li>\n<li>determine whether a given alcohol should be prepared by oxymercuration-demercuration or by hydroboration-oxidation, and identify the alkene and reagents required to carry out such a synthesis.<\/li>\n<li>write the detailed mechanism for the addition of borane to an alkene, and explain the stereochemistry and regiochemistry of the reaction.<\/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 class=\"boxtitle\">Key Terms<\/h3>\n<p>Make certain that you can define, and use in context, the key term below.<\/p>\n<ul>\n<li>hydroboration<\/li>\n<\/ul>\n<\/div>\n<div class=\"textbox\">\n<div><\/div>\n<div id=\"note\">\n<h3 class=\"boxtitle\">Study Notes<\/h3>\n<p>The two most important factors influencing organic reactions are polar (or electronic) effects and steric effects.<\/p>\n<\/div>\n<\/div>\n<\/div>\n<p>Hydroboration-Oxidation is a two step pathway used\u00a0to produce\u00a0alcohols. The reaction proceeds in an <a class=\"internal\" title=\"Wikitexts\/UCD Chem 118B\/Chem 118B Topics\/Radical Additions--Anti-Markovnikov Product Formation\" href=\"\/Organic_Chemistry\/Hydrocarbons\/Alkenes\/Reactions_of_Alkenes\/Radical_Additions--Anti-Markovnikov_Product_Formation\" rel=\"internal\">Anti-Markovnikov<\/a> manner, where the\u00a0hydrogen (from BH<sub>3<\/sub> or BHR<sub>2<\/sub>) attaches to the more substituted carbon and the boron\u00a0attaches to the\u00a0least substituted carbon in the <a class=\"internal\" title=\"Organic Chemistry\/Hydrocarbons\/Alkenes\" href=\"\/Organic_Chemistry\/Hydrocarbons\/Alkenes\" rel=\"internal\">alkene<\/a> bouble bond. Furthermore, the borane acts as a lewis acid by\u00a0accepting two electrons in its empty p\u00a0orbital\u00a0from\u00a0an alkene that is electron rich. This process allows boron to have\u00a0an electron octet.\u00a0 A very interesting characteristic of this process is that it does not require any activation\u00a0by a catalyst.\u00a0The Hydroboration mechanism\u00a0has\u00a0the elements of both hydrogenation and <a class=\"internal\" title=\"Wikitexts\/UCD Chem 118B\/Chem 118B Topics\/Electrophilic Attack on Conjugated Dienes\/Electrophile\" href=\"\/Organic_Chemistry\/Conjugation\/Electrophilic_Attack_on_Conjugated_Dienes\/Electrophile\" rel=\"internal\">electrophilic<\/a> addition\u00a0and it is\u00a0a stereospecific\u00a0(<strong><em>syn addition),<\/em><\/strong> meaning that the\u00a0hydroboration takes place on the same\u00a0face of the double bond, this leads <em><strong>cis<\/strong><\/em> stereochemistry.<\/p>\n<div>\n<div id=\"section_1\">\n<h3 class=\"editable\">Introduction<\/h3>\n<p>Hydroboration-oxidation of alkenes has been a very valuable laboratory method for the stereoselectivity and regioselectivity of alkenes. An Additional feature of this reaction is that it occurs without rearrangement.<\/p>\n<\/div>\n<\/div>\n<div>\n<div id=\"section_2\">\n<h3 class=\"editable\">The Borane Complex<\/h3>\n<p>First off it is very imporatnt to understand\u00a0little bit\u00a0about the structure and the properties of the borane molecule. Borane exists naturally as a very toxic gas and it exists as dimer of the general formula B<sub>2<\/sub>H<sub>6<\/sub> (diborane). Additionally, the dimer B<sub>2<\/sub>H<sub>6<\/sub>ignites spontaneously in air. Borane is commercially available in ether and tetrahydrofuran (THF), in these solutions the borane can exist as a lewis acid-base complex, which allows boron to have an electron octet.BH3\u2192B2H6<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/2058\/THF.bmp?revision=1&amp;size=bestfit&amp;width=451&amp;height=122#fixme\" alt=\"THF.bmp\" width=\"451px\" height=\"122px\" \/><\/p>\n<\/div>\n<\/div>\n<div>\n<div id=\"section_3\">\n<h3 class=\"editable\">The Mechanism<\/h3>\n<div class=\"editIcon\"><\/div>\n<div>\n<div id=\"section_4\">\n<h4 class=\"editable\"><strong>Step #1<\/strong><\/h4>\n<ul>\n<li>Part #1: Hydroboration of the alkene. In this first step the addittion of the borane to the alkene is initiated and prceeds as a concerted reaction because bond breaking and bond formation occurs at the same time. This part consists of the vacant 2p orbital of the boron electrophile pairing with the electron pair of the ? bondof the nucleophile.<\/li>\n<\/ul>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/2049\/concerted_reaction_1.bmp?revision=1&amp;size=bestfit&amp;width=260&amp;height=191#fixme\" alt=\"concerted reaction 1.bmp\" width=\"260px\" height=\"191px\" \/><\/p>\n<p><strong>Transition state<\/strong><\/p>\n<p><strong><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/2059\/TRANSITION_STATE_FINAL_2_(2).bmp?revision=1&amp;size=bestfit&amp;width=441&amp;height=242#fixme\" alt=\"TRANSITION STATE FINAL 2 (2).bmp\" width=\"441px\" height=\"242px\" \/><\/strong><\/p>\n<p><strong>* Note that a carbocation is not formed. Therefore, no rearrangement takes place<\/strong>.<\/p>\n<ul>\n<li>Part #2: The Anti Markovnikov addition of Boron. The boron adds to the less substituted carbon of the alkene, which then places the hydrogen on the more substituted carbon. Both, the boron and the hydrogen add simultaneously on the same face of the double bond (syn addition).<\/li>\n<\/ul>\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\/05142202\/borination_step_2.gif\" alt=\"borination step 2.gif\" width=\"226\" height=\"79\" \/><\/p>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div>\n<div id=\"section_5\">\n<h3 class=\"editable\">Oxidation of the Trialkylborane by Hydrogen Peroxide<\/h3>\n<div>\n<div id=\"section_6\">\n<h4 class=\"editable\">Step #2<\/h4>\n<ul>\n<li>Part #1: the first part of this mechanism deals with the donation of a pair of electrons from the hydrogen peroxide ion. the hydrogen peroxide is the nucleophile in this reaction because it is the electron donor to the newly formed trialkylborane that resulted from hydroboration.<\/li>\n<\/ul>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/2052\/peorxide_1.bmp?revision=1&amp;size=bestfit&amp;width=582&amp;height=57#fixme\" alt=\"peorxide 1.bmp\" width=\"582px\" height=\"57px\" \/><\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/2051\/oxidation_part_1_(1).bmp?revision=1&amp;size=bestfit&amp;width=696&amp;height=239#fixme\" alt=\"oxidation part 1 (1).bmp\" width=\"696px\" height=\"239px\" \/><\/p>\n<ul>\n<li>Part 2: In this second part of the mechanism, a rearrangement of an R group with its pair of bonding electrons to an adjacent oxygen results in the removal of a hydroxide ion.<\/li>\n<\/ul>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/2042\/1%252C2%252C_SHIFT.bmp?revision=1&amp;size=bestfit&amp;width=655&amp;height=172#fixme\" alt=\"1,2, SHIFT.bmp\" width=\"655px\" height=\"172px\" \/><\/p>\n<p><strong>Two more of these reactions with hydroperoxide will occur in order give a trialkylborate<\/strong><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/2060\/trialkylborate.bmp?revision=1#fixme\" alt=\"trialkylborate.bmp\" width=\"515\" height=\"168\" \/><\/p>\n<ul>\n<li>Part 3: This is the final part of the Oxidation process. In this part the trialkylborate reacts with aqueous NaOH to give the alcohol and sodium borate.<\/li>\n<\/ul>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/2057\/Sodium_Borate.bmp?revision=1&amp;size=bestfit&amp;width=668&amp;height=60#fixme\" alt=\"Sodium Borate.bmp\" width=\"668px\" height=\"60px\" \/><\/p>\n<p>If you need additional visuals to aid you in understanding the mechanism, click on the outside links provided here that will take you to other pages and media that are very helpful as well.<\/p>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div>\n<div id=\"section_7\">\n<h3 class=\"editable\">Stereochemistry of hydroboration<\/h3>\n<p>The hydroboration reaction is among the few simple addition reactions that proceed cleanly in a <em>syn <\/em>fashion. As noted above, this is a single-step reaction. Since the bonding of the double bond carbons to boron and hydrogen is concerted, it follows that the geometry of this addition must be syn. Furthermore, rearrangements are unlikely inasmuch as a discrete carbocation intermediate is never formed. These features are illustrated for the hydroboration of \u03b1-pinene.<\/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\/05142204\/pinene3.gif\" alt=\"image\" \/><\/p>\n<p>Since the hydroboration procedure is most commonly used to hydrate alkenes in an anti-Markovnikov fashion, we also need to know the stereoselectivity of the second oxidation reaction, which substitutes a hydroxyl group for the boron atom. Independent study has shown this reaction takes place with retention of configuration so the overall addition of water is also syn.<\/p>\n<p>The hydroboration of \u03b1-pinene also provides a nice example of steric hindrance control in a chemical reaction. In the less complex alkenes used in earlier examples the plane of the double bond was often a plane of symmetry, and addition reagents could approach with equal ease from either side. In this case, one of the methyl groups bonded to C-6 (colored blue in the equation) covers one face of the double bond, blocking any approach from that side. All reagents that add to this double bond must therefore approach from the side opposite this methyl.<\/p>\n<\/div>\n<div id=\"section_8\">\n<h3 class=\"editable\">Outside links<\/h3>\n<ul>\n<li><a class=\"external\" title=\"http:\/\/en.wikipedia.org\/wiki\/Hydroboration-oxidation\" href=\"http:\/\/en.wikipedia.org\/wiki\/Hydroboration-oxidation\" target=\"_blank\" rel=\"external nofollow noopener\">http:\/\/en.wikipedia.org\/wiki\/Hydroboration-oxidation<\/a><\/li>\n<li><a class=\"external\" title=\"http:\/\/bcs.whfreeman.com\/vollhardtschore4e\/cat_010\/ch12\/12010-03.htm\" href=\"http:\/\/bcs.whfreeman.com\/vollhardtschore4e\/cat_010\/ch12\/12010-03.htm\" target=\"_blank\" rel=\"external nofollow noopener\">http:\/\/bcs.whfreeman.com\/vollhardtschore4e\/cat_010\/ch12\/12010-03.htm<\/a><\/li>\n<li><a class=\"external\" title=\"http:\/\/www.chemhelper.com\/hydroboration.html\" href=\"http:\/\/www.chemhelper.com\/hydroboration.html\" target=\"_blank\" rel=\"external nofollow noopener\">http:\/\/www.chemhelper.com\/hydroboration.html<\/a><\/li>\n<li><a class=\"external\" title=\"http:\/\/www.cartage.org.lb\/en\/themes\/sciences\/chemistry\/Organicchemistry\/CommonReactio\/Hydroboration\/Hydroboration.htm\" href=\"http:\/\/www.cartage.org.lb\/en\/themes\/sciences\/chemistry\/Organicchemistry\/CommonReactio\/Hydroboration\/Hydroboration.htm\" target=\"_blank\" rel=\"external nofollow noopener\">http:\/\/www.cartage.org.lb\/en\/themes\/&#8230;roboration.htm<\/a><\/li>\n<li><a class=\"external\" title=\"http:\/\/www.organic-chemistry.org\/namedreactions\/brown-hydroboration.shtm\" href=\"http:\/\/www.organic-chemistry.org\/namedreactions\/brown-hydroboration.shtm\" target=\"_blank\" rel=\"external nofollow noopener\">http:\/\/www.organic-chemistry.org\/nam&#8230;oboration.shtm<\/a><\/li>\n<\/ul>\n<\/div>\n<\/div>\n<div>\n<div id=\"section_9\">\n<h3 class=\"editable\">References<\/h3>\n<ol>\n<li>Vollhardt, Peter, and Neil Shore.\u00a0<u>Organic Chemistry: Structure and Function<\/u>. 5th. New York: W.H. Freeman and Company, 2007.<\/li>\n<li>Foote, S. Christopher, and William H. Brown. <u>Organic Chemistry<\/u>. 5th. Belmont, CA: Brooks\/Cole Cengage Learning, 2005.<\/li>\n<li>Bruice, Paula Yurkanis. <u>Oragnic Chemistry<\/u>. 5th. CA. Prentice Hall, 2006.<\/li>\n<li>Bergbreiter E. David , and David P. Rainville. <u>Stereochemistry of hydroboration-oxidation of terminal alkenes.<\/u>\u00a0<cite>J. Org. Chem.<\/cite>, <span class=\"citation_year\">1976<\/span>, <span class=\"citation_volume\">41<\/span> (18), pp 3031\u20133033<\/li>\n<li>Ilich, Predrag-Peter; Rickertsen, Lucas S., and Becker Erienne. <u>Polar Addition to C=C Group: Why Is Anti-Markovnikov Hydroboration-Oxidation of Alkenes Not &#8220;Anti-&#8220;?<\/u> Journal of Chemical Education., 2006, v83, n11, pg 1681-1685<\/li>\n<\/ol>\n<\/div>\n<\/div>\n<div>\n<div id=\"section_10\">\n<div class=\"textbox examples\">\n<h3>Examples<\/h3>\n<div>\n<div id=\"section_10\">\n<h3 class=\"editable\">Problems<\/h3>\n<p><strong>What are the products of these following reactions? <\/strong><\/p>\n<p><strong>#1.\u00a0<\/strong><\/p>\n<p><strong><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/2055\/PROBLEM_1.bmp?revision=1&amp;size=bestfit&amp;width=167&amp;height=84#fixme\" alt=\"PROBLEM 1.bmp\" width=\"167px\" height=\"84px\" \/><\/strong><\/p>\n<p><strong>#2.<\/strong><\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/2054\/PROBLEM_%25232.bmp?revision=1&amp;size=bestfit&amp;width=308&amp;height=91#fixme\" alt=\"PROBLEM #2.bmp\" width=\"308px\" height=\"91px\" \/><\/p>\n<p><strong>#3.<\/strong><\/p>\n<p><strong><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/2053\/PROBELM_%25233.bmp?revision=1&amp;size=bestfit&amp;width=445&amp;height=121#fixme\" alt=\"PROBELM #3.bmp\" width=\"445px\" height=\"121px\" \/><\/strong><\/p>\n<p><strong>Draw the structural formulas for the alcohols that result from \u00a0hydroboration-oxidation of the alkenes shown.<\/strong><\/p>\n<p><strong>#4.<\/strong><\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/2056\/problem_4.bmp?revision=1&amp;size=bestfit&amp;width=132&amp;height=80#fixme\" alt=\"problem 4.bmp\" width=\"132px\" height=\"80px\" \/><\/p>\n<p><strong>#5. (E)-3-methyl-2-pentene\u00a0 <\/strong><\/p>\n<p>If you need clarification or a reminder on the nomenclature of alkenes refer to the link below on naming the <a class=\"internal\" title=\"Organic Chemistry\/Hydrocarbons\/Alkenes\" href=\"\/Organic_Chemistry\/Hydrocarbons\/Alkenes\" rel=\"internal\">alkenes.<\/a><\/p>\n<\/div>\n<\/div>\n<div>\n<div id=\"section_11\">\n<h3 class=\"editable\"><strong>Answers<\/strong><\/h3>\n<div class=\"editIcon\">\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q760849\">Show Answer<\/span><\/p>\n<div id=\"q760849\" class=\"hidden-answer\" style=\"display: none\">#1.<img decoding=\"async\" class=\"internal default alignnone\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/2043\/answer_%25231.bmp?revision=1&amp;size=bestfit&amp;width=111&amp;height=83#fixme\" alt=\"answer #1.bmp\" width=\"111px\" height=\"83px\" \/>#2.<img loading=\"lazy\" decoding=\"async\" class=\"internal default alignnone\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05142206\/hydrobor_prob2_soln.png\" alt=\"hydrobor prob2 soln.png\" width=\"121\" height=\"78\" \/>#3.<img decoding=\"async\" class=\"internal default alignnone\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/2044\/Answer_%25233.bmp?revision=1&amp;size=bestfit&amp;width=245&amp;height=151#fixme\" alt=\"Answer #3.bmp\" width=\"245px\" height=\"151px\" \/>#4.<img decoding=\"async\" class=\"internal default alignnone\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/2045\/ANSWER_%25234.bmp?revision=1&amp;size=bestfit&amp;width=153&amp;height=113#fixme\" alt=\"ANSWER #4.bmp\" width=\"153px\" height=\"113px\" \/>#5.<img decoding=\"async\" class=\"internal default alignnone\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/2046\/Answer_5.bmp?revision=1&amp;size=bestfit&amp;width=183&amp;height=98#fixme\" alt=\"Answer 5.bmp\" width=\"183px\" height=\"98px\" \/><\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_12\"><\/div>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_12\">\n<div class=\"textbox exercises\">\n<h3 class=\"editable\">Exercises<\/h3>\n<div id=\"section_13\">\n<h4 class=\"editable\">Question<\/h4>\n<ol>\n<li>Write out the reagents or products (A\u2013D) shown in the following reaction schemes.<\/li>\n<\/ol>\n<p><img decoding=\"async\" class=\"aligncenter\" src=\"http:\/\/chem.libretexts.org\/@api\/deki\/files\/84939\/8-5exercise.png?origin=mt-web\" alt=\"alkene hydration reaction questions\" \/><\/p>\n<\/div>\n<div id=\"section_14\">\n<h3 class=\"editable\">Solution<\/h3>\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q466385\">Show Answer<\/span><\/p>\n<div id=\"q466385\" class=\"hidden-answer\" style=\"display: none\">\n<p><img decoding=\"async\" class=\"aligncenter\" src=\"http:\/\/chem.libretexts.org\/@api\/deki\/files\/84936\/8-5answer.png?origin=mt-web\" alt=\"alkene hydration reaction answers\" \/><\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_15\">\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","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-1085","chapter","type-chapter","status-publish","hentry"],"part":24,"_links":{"self":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/1085","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\/1085\/revisions"}],"predecessor-version":[{"id":2301,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/1085\/revisions\/2301"}],"part":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/parts\/24"}],"metadata":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/1085\/metadata\/"}],"wp:attachment":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/media?parent=1085"}],"wp:term":[{"taxonomy":"chapter-type","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapter-type?post=1085"},{"taxonomy":"contributor","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/contributor?post=1085"},{"taxonomy":"license","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/license?post=1085"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}