{"id":1077,"date":"2017-10-19T14:11:47","date_gmt":"2017-10-19T14:11:47","guid":{"rendered":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/?post_type=chapter&#038;p=1077"},"modified":"2018-10-03T20:29:36","modified_gmt":"2018-10-03T20:29:36","slug":"hydration-of-alkenes-oxymercuration","status":"publish","type":"chapter","link":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/chapter\/hydration-of-alkenes-oxymercuration\/","title":{"raw":"Hydration of Alkenes: Oxymercuration","rendered":"Hydration of Alkenes: Oxymercuration"},"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 class=\"elm-header\"><\/div>\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>write an equation for the hydration of an alkene with sulfuric acid.<\/li>\r\n \t<li>write an equation for the formation of an alcohol from an alkene by the oxymercuration-demercuration process.<\/li>\r\n \t<li>identify the alkene, the reagents, or both, that should be used to produce a given alcohol by the oxymercuration-demercuration process.<\/li>\r\n \t<li>write the mechanism for the reaction of an alkene with mercury(II) acetate in aqueous tetrahydrofuran (THF).<\/li>\r\n<\/ol>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div class=\"textbox key-takeaways\">\r\n<h3>KeY Terms<\/h3>\r\n<div class=\"elm-header\">\r\n<div class=\"elm-header-custom\">\r\n\r\nMake certain that you can define, and use in context, the key terms below.\r\n\r\n<\/div>\r\n<\/div>\r\n<div id=\"elm-main-content\" class=\"elm-content-container\">\r\n<div>\r\n<ul>\r\n \t<li>hydration<\/li>\r\n \t<li>oxymercuration<\/li>\r\n<\/ul>\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 id=\"note\">\r\n<div class=\"textbox\">\r\n<h3 class=\"boxtitle\">Study Notes<\/h3>\r\n<em>Oxymercuration<\/em> is the reaction of an alkene with mercury(II) acetate in aqueous THF, followed by reduction with sodium borohydride. The final product is an alcohol.\r\n\r\nIt is important that you recognize the similarity between the mechanisms of bromination and oxymercuration. Recognizing these similarities helps you to reduce the amount of factual material that you need to remember.\r\n\r\nMercuric acetate, or mercury(II) acetate, to give it the preferred IUPAC name, is written as Hg(OAc)<sub>2<\/sub>; by comparing this formula with the formula Hg(O<sub>2<\/sub>CCH<sub>3<\/sub>)<sub>2<\/sub>, you can equate Ac with OCCH<sub>3<\/sub>. In fact, Ac is an abbreviation used for the acetyl group with the structure shown below as are other similar abbreviations that you will encounter.<img class=\"aligncenter\" src=\"http:\/\/chem.libretexts.org\/@api\/deki\/files\/84937\/8-4.png?origin=mt-web\" alt=\"table of common functional group abbreviations\" \/>\r\n\r\n&nbsp;\r\n\r\n<\/div>\r\n<\/div>\r\nElectrophilic\u00a0hydration is the act of adding electrophilic hydrogen from a non-nucleophilic strong acid (a reusable catalyst,\u00a0examples of which include sulfuric and phosphoric acid) and applying appropriate temperatures to break the alkene's double bond. After a <a title=\"Carbocation Rearrangements\" href=\"https:\/\/chem.libretexts.org\/Core\/Organic_Chemistry\/Reactions\/Elimination_Reactions\/E1_Reactions\/Carbocation_Rearrangements\" rel=\"internal\">carbocation <\/a>is formed, water bonds with the carbocation to form a 1\u00ba, 2\u00ba, or 3\u00ba alcohol on the alkane.\r\n<div id=\"section_1\">\r\n<h3 class=\"editable\">What Is Electrophilic Hydration?<\/h3>\r\nElectrophilic\u00a0hydration\u00a0is the reverse <a class=\"internal mt-disabled\" title=\"Wikitexts\/UCD Chem 118B\/Chem 118B Topics\/Alkenes by Dehydration of Alcohols\" rel=\"broken\">dehydration of alcohols<\/a> and has practical application in\u00a0making alcohols for fuels and reagents for other reactions. The basic reaction under certain temperatures (given below) is the following:\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/1348\/Basic_Electrophilic_Hydration.bmp?revision=1&amp;size=bestfit&amp;width=521&amp;height=122#fixme\" alt=\"Basic Electrophilic Hydration.bmp\" width=\"521px\" height=\"122px\" \/>\r\n\r\nThe phrase \"electrophilic\"\u00a0literally means \"electron loving\"\u00a0(whereas \"nucleophilic\" means \"nucleus loving\"). Electrophilic hydrogen is essentially a proton: a hydrogen atom stripped of its electrons. Electrophilic hydrogen is commonly used to help break double bonds or restore catalysts (see <a title=\"Organic Chemistry\/Reactions\/SN2 Reaction\" href=\"https:\/\/chem.libretexts.org\/Core\/Organic_Chemistry\/Reactions\/Substitution_Reactions\/SN2\" rel=\"internal\">S<sub>N<\/sub>2<\/a> for more details).\r\n\r\n<\/div>\r\n<div id=\"section_2\">\r\n<h3 class=\"editable\">How Does Electrophilic Hydration Work?<\/h3>\r\n<div id=\"section_3\">\r\n<h4 class=\"editable\">Mechanism for 3\u00ba Alcohol (1\u00ba and 2\u00ba mechanisms are similar):<\/h4>\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05142003\/Electrophilic_Hydration_Mechanism.jpg\" alt=\"Electrophilic Hydration Mechanism.jpg\" width=\"692px\" height=\"303px\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_4\">\r\n<h4 class=\"editable\">Temperatures for Types of Alcohol Synthesis<\/h4>\r\nHeat is used to catalyze electrophilic hydration;\u00a0because the reaction is in equilibrium with the dehydration of an alcohol, which requires higher temperatures to form an alkene, lower temperatures are required to form an alcohol.\u00a0<em>The exact temperatures used are highly variable and depend on the product being formed.<\/em>\r\n<ul>\r\n \t<li>Primary Alcohol:\u00a0 Less than 170\u00baC<\/li>\r\n \t<li>Secondary Alcohol:\u00a0 Less than 100\u00baC<\/li>\r\n \t<li>Tertiary Alcohol:\u00a0 Less than 25\u00baC<\/li>\r\n<\/ul>\r\n<\/div>\r\n<div id=\"section_5\">\r\n<h4 class=\"editable\">But...Why Does Electrophilic Hydration Work?<\/h4>\r\n<ul>\r\n \t<li>An alkene placed in an aqueous non-nucleophilic strong acid immediately \"reaches out\" with its double bond and attacks one of the acid's hydrogen atoms\u00a0(meanwhile, the bond between oxygen and hydrogen performs heterolytic cleavage toward\u00a0the oxygen\u2014in other words, both electrons from the oxygen\/hydrogen single bond move onto the oxygen atom).<\/li>\r\n \t<li>A carbocation is formed on the original alkene (now alkane) in the more-substituted position, where the oxygen end of water attacks with its 4 non-bonded valence electrons (oxygen has 6 total valence electrons because it is found in Group 6 on the periodic table and the second row down: two electrons in a 2s-orbital and four in 2p-orbitals. Oxygen donates one valence electron to each bond it forms, leaving four\u00a04 non-bonded valence electrons).<\/li>\r\n \t<li>After the blue oxygen atom forms its third bond with the more-substituted carbon, it develops a positive charge (3 bonds and 2 valence electrons give the blue oxygen atom\u00a0a formal charge of +1).<\/li>\r\n \t<li>The bond between the green hydrogen and the blue oxygen undergoes heterolytic cleavage, and both the electrons from the bond move onto the blue oxygen.\u00a0 The now negatively-charged strong acid picks up the green electrophilic hydrogen.<\/li>\r\n \t<li>Now that the reaction is complete, the non-nucleophilic strong acid is regenerated as a catalyst and an alcohol forms on the most\u00a0substituted carbon of the current alkane. At lower temperatures, more alcohol product can be formed.<\/li>\r\n<\/ul>\r\n<\/div>\r\n<div id=\"section_6\">\r\n<h4 class=\"editable\">What is Regiochemistry and How Does It Apply?<\/h4>\r\nRegiochemistry deals with where the substituent bonds on the product. <strong>Zaitsev<\/strong>'s and <strong><a title=\"Organic Chemistry\/Conjugation\/Electrophilic Attack on Conjugated Dienes\/Markovnikov Addition\" href=\"https:\/\/chem.libretexts.org\/Core\/Organic_Chemistry\/Conjugation\/Electrophilic_Attack_on_Conjugated_Dienes\/Markovnikov_Addition\" rel=\"internal\">Markovnikov<\/a><\/strong>'s rules address regiochemistry, but Zaitsev's\u00a0rule applies when synthesizing an alkene while Markovnikov's\u00a0rule describes where the substituent bonds\u00a0onto the product. In the case of\u00a0electrophilic hydration, Markovnikov's\u00a0rule is the only rule that <em>directly<\/em> applies. See the following for an in-depth explanation of regiochemistry Markovnikov explanation: <a class=\"internal mt-disabled\" title=\"Wikitexts\/UCD Chem 118B\/Chem 118B Topics\/Radical Additions--Anti-Markovnikov Product Formation\" rel=\"broken\">Radical Additions--Anti-Markovnikov Product Formation<\/a>\r\n\r\nIn the mechanism for a 3\u00ba alcohol shown above, the red H is added to the least-substituted carbon\u00a0connected to the nucleophilic double bonds (it has less carbons attached to it).\u00a0This means that the carbocation forms on the 3\u00ba carbon, causing it to be highly stabilized by <em>hyperconjugation<\/em><em>\u2014<\/em>electrons in nearby sigma (single) bonds help fill the empty p-orbital of the carbocation, which lessens the positive charge.\u00a0More substitution on a carbon means more sigma bonds are available to \"help out\" (by using overlap) with the positive charge, which creates greater\u00a0<em>carbocation stability<\/em>.\u00a0In other words,\u00a0<strong>carbocations\u00a0form on the most substituted carbon<\/strong>\u00a0connected to the double bond. Carbocations are also stabilized by resonance, but resonance is not a large factor in this case because any carbon-carbon double bonds are used to initiate the reaction, and other double bonded molecules can cause a completely different reaction.\r\n\r\nIf the carbocation does originally form on the less substituted part of the alkene, carbocation rearrangements occur to form more substituted products:\r\n<ul>\r\n \t<li><strong>Hydride shifts:<\/strong>\u00a0a hydrogen atom bonded to a carbon atom next to the carbocation\u00a0leaves that carbon to bond with the carbocation (after the hydrogen has taken both electrons from the single bond, it is known as a hydride).\u00a0This changes the once neighboring carbon to a carbocation, and the former carbocation becomes a neighboring carbon atom.<\/li>\r\n<\/ul>\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/1350\/Hydride_Shift.bmp?revision=1&amp;size=bestfit&amp;width=415&amp;height=111#fixme\" alt=\"Hydride Shift.bmp\" width=\"415px\" height=\"111px\" \/>\r\n<ul>\r\n \t<li><strong>Alkyl shifts:<\/strong>\u00a0 if\u00a0no hydrogen atoms are\u00a0available for a hydride shift, an entire methyl group performs the same shift.<\/li>\r\n<\/ul>\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/1347\/Alkyl_Shift.bmp?revision=1&amp;size=bestfit&amp;width=494&amp;height=149#fixme\" alt=\"Alkyl Shift.bmp\" width=\"494px\" height=\"149px\" \/>\r\n\r\nThe nucleophile\u00a0attacks the positive charge\u00a0formed on the most substituted carbon connected to the double bond, because the nucleophile is seeking that positive charge.\u00a0In the mechanism for a 3\u00ba alcohol shown above, water is the nucleophile.\u00a0When the green H is removed from the water molecule,\u00a0the alcohol attached to the most substituted carbon. Hence, <strong>electrophilic hydration follows Markovnikov's\u00a0rule.<\/strong>\r\n\r\n<\/div>\r\n<div id=\"section_7\">\r\n<h3 class=\"editable\">What is Stereochemistry and How Does It Apply?<\/h3>\r\n<strong>Stereochemistry deals with how the substituent\u00a0bonds\u00a0on the product directionally<\/strong>. Dashes and wedges denote stereochemistry by showing whether the molecule or atom is going into or out of the plane of the board. Whenever the bond is a simple single straight line, the molecule that is bonded is equally likely to be found going into the plane of the board as it is out of the plane of the board. This indicates that\u00a0<strong>the product is a racemic mixture<\/strong>.\r\n\r\nElectrophilic hydration adopts a stereochemistry wherein the substituent is equally likely to bond pointing into the plane of the board as it is pointing out of the plane of the board. The 3\u00ba alcohol product could look like either of the following products:\r\n\r\n<a title=\"Tert Alcohol Stereochemistry.bmp\" href=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/1361\/Tert_Alcohol_Stereochemistry.bmp?revision=1\" rel=\"internal\"><img class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/1361\/Tert_Alcohol_Stereochemistry.bmp?revision=1&amp;size=bestfit&amp;width=720&amp;height=144#fixme\" alt=\"Tert Alcohol Stereochemistry.bmp\" width=\"720px\" height=\"144px\" \/><\/a>\r\n\r\nNote:\u00a0 Whenever a straight line is used along with dashes and wedges on the same molecule, it could be denoting that the straight line bond is in the same plane as the board. Practice with a molecular model kit and attempting the practice problems at the end can help eliminate any ambiguity.\r\n\r\n<\/div>\r\n<div id=\"section_8\">\r\n<h4 class=\"editable\">Is this a Reversible Synthesis?<\/h4>\r\nElectrophilic hydration is reversible because an alkene in water is in equilibrium with the alcohol product.\u00a0To sway the equilibrium one way or another, the temperature or the concentration of the non-nucleophilic\u00a0strong acid\u00a0can be changed. For example:\r\n<ul>\r\n \t<li>Less sulfuric or phosphoric acid and an excess of water help synthesize more alcohol product.<\/li>\r\n \t<li>Lower temperatures help synthesize more alcohol product.<\/li>\r\n<\/ul>\r\n<\/div>\r\n<div id=\"section_9\">\r\n<h4 class=\"editable\">Is There a Better Way to Add Water to Synthesize an Alcohol From an Alkene?<\/h4>\r\nA more efficient pathway does exist: see <a class=\"internal mt-disabled\" title=\"Wikitexts\/UCD Chem 118B\/Chem 118B Topics\/Oxymercuration - Demercuration\" rel=\"broken\">Oxymercuration - Demercuration: A Special Electrophilic Addition<\/a>.\u00a0\u00a0Oxymercuration does not allow for rearrangements, but it does require the use of mercury, which is highly toxic. Detractions for using electrophilic hydration to make alcohols include:\r\n<ul>\r\n \t<li>Allowing for carbocation rearrangements<\/li>\r\n \t<li>Poor yields due to the reactants and products being in equilibrium<\/li>\r\n \t<li>Allowing for product mixtures (such as an (R)-enantiomer and an (S)-enantiomer)<\/li>\r\n \t<li>Using sulfuric or phosphoric acid<\/li>\r\n<\/ul>\r\nOxymercuration is a special electrophilic addition. It is anti-stereospecific and regioselective. Regioselectivity is a process in which the substituents choses one direction it prefers to be attached to over all the other possible directions. The good thing about this reaction is that there are no <a title=\"Carbocation Rearrangements\" href=\"https:\/\/chem.libretexts.org\/Core\/Organic_Chemistry\/Reactions\/Elimination_Reactions\/E1_Reactions\/Carbocation_Rearrangements\" rel=\"internal\">carbocation rearrangement<\/a> due to stabilization of the reactive intermediate. Similar stabilization is also seen in <a title=\"The Reaction with Bromine\" href=\"https:\/\/chem.libretexts.org\/Core\/Organic_Chemistry\/Reactions\/Addition_Reactions\/Electrophilic_Addition_Reactions\/Reactions_of_Alkenes_with_Bromine\" rel=\"internal\">bromination <\/a>addition to alkenes.\r\n\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_10\">\r\n<h3 class=\"editable\">Introduction<\/h3>\r\nCarbocation rearrangement is a process in which the carbocation intermediate can form a more stable ion. With <a class=\"internal\" title=\"Organic Chemistry\/Reactions\/E1 Reaction\/Carbocation Rearrangements\" href=\"https:\/\/chem.libretexts.org\/Core\/Organic_Chemistry\/Reactions\/Elimination_Reactions\/E1_Reactions\/Carbocation_Rearrangements\" rel=\"internal\">carbocation rearrangement<\/a>, the reaction would not be able to hydrate quickly under mild conditions and be produced in high yields. This reaction is very fast and proceeds with 90% yield.\r\n\r\n<img src=\"https:\/\/chem.libretexts.org\/LibreTexts\/Athabasca_University\/Chemistry_350%3A_Organic_Chemistry_I\/Chapter_8%3A_Alkenes%3A_Reactions_and_Synthesis\/denied:data:image\/png;base64,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#fixme\" alt=\"\" \/>\r\n\r\nThis reaction involves a mercury acting as a reagent attacking the alkene double bond to form a <em>Mercurinium Ion Bridge<\/em>. A water molecule will then attack the most substituted carbon to open the mercurium ion bridge, followed by proton transfer to solvent water molecule.\r\n\r\n<img 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alt=\"\" \/>\r\n\r\nThe organomercury intermediate is then reduced by sodium borohydride - the mechanism for this final step is beyond the scope of our discussion here. Notice that overall, the oxymercuration - demercuration mechanism follows <a title=\"Regioselectivity and the Markovnikov Rule\" rel=\"broken\">Markovnikov's Regioselectivity<\/a> with the OH group is attached to the most substituted carbon and the H is attach to the least substituted carbon. The reaction is useful, however, because strong acids are not required, and carbocation rearrangements are avoided because no discreet carbocation intermediate forms.\r\n\r\n<\/div>\r\n<div id=\"section_11\">\r\n<h3 class=\"editable\">References<\/h3>\r\n<ol>\r\n \t<li>Vollhardt, K. Peter C. Organic chemistry structure and function. New York: W.H. Freeman, 2007.<\/li>\r\n \t<li>Smith, Michael B., and Jerry March. March's Advanced Organic Chemistry Reactions, Mechanisms, and Structure (March's Advanced Organic Chemistry). New York: Wiley-Interscience, 2007 2007.<\/li>\r\n \t<li><a class=\"external\" title=\"http:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00435a033\" href=\"http:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00435a033\" target=\"_blank\" rel=\"external nofollow noopener\">Roderic P. Quirk , <\/a><a class=\"external\" href=\"http:\/\/pubs.acs.org\/action\/doSearch?ContribStored=Lea%2C+Robert+E.\" target=\"_blank\" rel=\"external nofollow noopener\">Robert E. <\/a><a class=\"external\" title=\"http:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00435a033\" href=\"http:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00435a033\" target=\"_blank\" rel=\"external nofollow noopener\">Lea, Reductive demercuration of hex-5-enyl-1-mercuric bromide by metal hydrides. Rearrangement, isotope effects, and mechanism<\/a><a class=\"external\" href=\"http:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00435a033\" target=\"_blank\" rel=\"external nofollow noopener\">, <\/a><a class=\"external\" title=\"http:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00435a033\" href=\"http:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00435a033\" target=\"_blank\" rel=\"external nofollow noopener\"><cite>J. Am. Chem. Soc.<\/cite>, 1976, 98 (19), pp 5973\u20135978<\/a>.<\/li>\r\n<\/ol>\r\n<\/div>\r\n<div id=\"section_12\">\r\n<div class=\"textbox examples\">\r\n<h3>Examples<\/h3>\r\n<div id=\"section_12\">\r\n<h3 class=\"editable\">Problem<\/h3>\r\nWhat are the end products of these reactants?<img class=\"aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/127217\/8-4_Question.jpg?revision=1\" alt=\"8-4 Question.jpg\" \/>\r\n\r\n<img src=\"https:\/\/chem.libretexts.org\/LibreTexts\/Athabasca_University\/Chemistry_350%3A_Organic_Chemistry_I\/Chapter_8%3A_Alkenes%3A_Reactions_and_Synthesis\/denied:data:image\/png;base64,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\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#fixme\" alt=\"\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_13\">\r\n<h3 class=\"editable\">Answer<\/h3>\r\n[reveal-answer q=\"345958\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"345958\"]\r\n\r\n<img class=\"aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/127215\/8-4_Answer.jpg?revision=1\" alt=\"8-4 Answer.jpg\" \/>The end product to these practice problems are pretty much very similar. First, you locate where the double bond is on the reactant side. Then, you look at what substituents are attached to each side of the double bond and add the OH group to the more substituent side and the hydrogen on the less substituent side.[\/hidden-answer]&nbsp;\r\n\r\n<\/div>\r\n<div id=\"section_14\">\r\n<h3 class=\"editable\">Problems<\/h3>\r\nPredict the product of each reaction.\r\n\r\n1)\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/1352\/PP1_Q_(1).bmp?revision=1&amp;size=bestfit&amp;width=326&amp;height=100#fixme\" alt=\"PP1 Q (1).bmp\" width=\"326px\" height=\"100px\" \/>\r\n\r\n2)\u00a0 How does the\u00a0cyclopropane group affect the reaction?\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/1354\/PP2_Q.bmp?revision=1&amp;size=bestfit&amp;width=307&amp;height=136#fixme\" alt=\"PP2 Q.bmp\" width=\"307px\" height=\"136px\" \/>\r\n\r\n3)\u00a0\u00a0 (Hint: What is different about this problem?)\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/1356\/PP3_Q.bmp?revision=1&amp;size=bestfit&amp;width=280&amp;height=174#fixme\" alt=\"PP3 Q.bmp\" width=\"280px\" height=\"174px\" \/>\r\n\r\n4)\u00a0\u00a0\u00a0 (Hint: Consider\u00a0stereochemistry.)\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/1358\/PP4_Q.bmp?revision=1&amp;size=bestfit&amp;width=450&amp;height=111#fixme\" alt=\"PP4 Q.bmp\" width=\"450px\" height=\"111px\" \/>\r\n\r\n5)\u00a0 Indicate any shifts as well as the major product:\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/1360\/PP5_Q.bmp?revision=1&amp;size=bestfit&amp;width=425&amp;height=201#fixme\" alt=\"PP5 Q.bmp\" width=\"425px\" height=\"201px\" \/>\r\n\r\n&nbsp;\r\n\r\n<\/div>\r\n<div id=\"section_15\">\r\n<h3 class=\"editable\">Answers to Practice Problems<\/h3>\r\n[reveal-answer q=\"154724\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"154724\"]\r\n\r\n1)\u00a0 This is a basic electrophilic hydration.\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/1351\/PP1_A.bmp?revision=1&amp;size=bestfit&amp;width=275&amp;height=157#fixme\" alt=\"PP1 A.bmp\" width=\"275px\" height=\"157px\" \/>\r\n\r\n2)\u00a0The answer is additional side products, but the major product formed is still the same (the product shown).\u00a0 Depending on the temperatures used, the cyclopropane may open up into a straight chain, which makes it unlikely that the major product will form (after the reaction, it is unlikely that the 3\u00ba carbon will remain as such).\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/1353\/PP2_A.bmp?revision=1&amp;size=bestfit&amp;width=213&amp;height=135#fixme\" alt=\"PP2 A.bmp\" width=\"213px\" height=\"135px\" \/>\r\n\r\n3)\u00a0A hydride shift actually occurs from the top of the 1-methylcyclopentane to where the carbocation had formed.\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/1355\/PP3_A_(1).bmp?revision=1&amp;size=bestfit&amp;width=290&amp;height=201#fixme\" alt=\"PP3 A (1).bmp\" width=\"290px\" height=\"201px\" \/>\r\n\r\n4)\u00a0 This reaction will\u00a0have poor yields due to a very unstable intermediate.\u00a0 For a brief moment, carbocations can form on the two center carbons, which are more stable than the outer two carbons.\u00a0 The carbocations have an sp2 hybridization, and when the water is added on, the carbons change their hybridization to sp3.\u00a0 This makes the methyl and alcohol groups equally likely to be found going into or out of the plane of the paper- the product is racemic.\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/1357\/PP4_A.bmp?revision=1&amp;size=bestfit&amp;width=343&amp;height=115#fixme\" alt=\"PP4 A.bmp\" width=\"343px\" height=\"115px\" \/>\r\n\r\n5) In the first picture shown below, an alkyl shift occurs but a hydride shift (which occurs faster) is possible.\u00a0\u00a0 Why doesn't a hydride shift occur?\u00a0 The answer is because the alkyl shift leads to a more stable product.\u00a0 There is a noticeable amount of side product that forms where the two methyl groups are, but the major product shown below is still the most significant due to the hyperconjugation that occurs by being in between the two cyclohexanes.\r\n\r\n<a title=\"PP5 A.bmp\" href=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/1359\/PP5_A.bmp?revision=1\" rel=\"internal\"><img class=\"internal default\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/1359\/PP5_A.bmp?revision=1&amp;size=bestfit&amp;width=720&amp;height=164#fixme\" alt=\"PP5 A.bmp\" width=\"720px\" height=\"164px\" \/><\/a>\r\n\r\n[\/hidden-answer]\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_16\">\r\n<div class=\"textbox exercises\">\r\n<h3>Exercises<\/h3>\r\n<div id=\"section_16\">\r\n<div id=\"s61713\">\r\n<div>\r\n<h3 id=\"Questions-61713\">Questions<\/h3>\r\n<strong>1.<\/strong>\r\n\r\nIn each case, predict the product(s) of these reactants of oxymercuration.\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\/05142007\/8-4qu.png\" alt=\"\" width=\"333\" height=\"199\" \/>\r\n\r\n<strong>2.<\/strong>\r\n\r\nPropose the alkene that was the reactant for each of these products of oxymercuration.\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\/05142009\/8-4-2qu.png\" alt=\"\" width=\"209\" height=\"240\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_17\">\r\n<h3 id=\"Solutions-61713\">Solutions<\/h3>\r\n[reveal-answer q=\"377863\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"377863\"]\r\n\r\n<strong>1.<\/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\/05142011\/8-4sol.png\" alt=\"\" width=\"532\" height=\"233\" \/>\r\n\r\n<strong>2.<\/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\/05142014\/8.42.png\" alt=\"\" width=\"475\" height=\"231\" \/>[\/hidden-answer]\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div><\/div>\r\n<\/div>\r\n<\/div>\r\n<div>\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>Lance Peery (UCD), Duyen Dao-Tran<\/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>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 class=\"elm-header\"><\/div>\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>write an equation for the hydration of an alkene with sulfuric acid.<\/li>\n<li>write an equation for the formation of an alcohol from an alkene by the oxymercuration-demercuration process.<\/li>\n<li>identify the alkene, the reagents, or both, that should be used to produce a given alcohol by the oxymercuration-demercuration process.<\/li>\n<li>write the mechanism for the reaction of an alkene with mercury(II) acetate in aqueous tetrahydrofuran (THF).<\/li>\n<\/ol>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div class=\"textbox key-takeaways\">\n<h3>KeY Terms<\/h3>\n<div class=\"elm-header\">\n<div class=\"elm-header-custom\">\n<p>Make certain that you can define, and use in context, the key terms below.<\/p>\n<\/div>\n<\/div>\n<div id=\"elm-main-content\" class=\"elm-content-container\">\n<div>\n<ul>\n<li>hydration<\/li>\n<li>oxymercuration<\/li>\n<\/ul>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"elm-main-content\" class=\"elm-content-container\">\n<div id=\"note\">\n<div class=\"textbox\">\n<h3 class=\"boxtitle\">Study Notes<\/h3>\n<p><em>Oxymercuration<\/em> is the reaction of an alkene with mercury(II) acetate in aqueous THF, followed by reduction with sodium borohydride. The final product is an alcohol.<\/p>\n<p>It is important that you recognize the similarity between the mechanisms of bromination and oxymercuration. Recognizing these similarities helps you to reduce the amount of factual material that you need to remember.<\/p>\n<p>Mercuric acetate, or mercury(II) acetate, to give it the preferred IUPAC name, is written as Hg(OAc)<sub>2<\/sub>; by comparing this formula with the formula Hg(O<sub>2<\/sub>CCH<sub>3<\/sub>)<sub>2<\/sub>, you can equate Ac with OCCH<sub>3<\/sub>. In fact, Ac is an abbreviation used for the acetyl group with the structure shown below as are other similar abbreviations that you will encounter.<img decoding=\"async\" class=\"aligncenter\" src=\"http:\/\/chem.libretexts.org\/@api\/deki\/files\/84937\/8-4.png?origin=mt-web\" alt=\"table of common functional group abbreviations\" \/><\/p>\n<p>&nbsp;<\/p>\n<\/div>\n<\/div>\n<p>Electrophilic\u00a0hydration is the act of adding electrophilic hydrogen from a non-nucleophilic strong acid (a reusable catalyst,\u00a0examples of which include sulfuric and phosphoric acid) and applying appropriate temperatures to break the alkene&#8217;s double bond. After a <a title=\"Carbocation Rearrangements\" href=\"https:\/\/chem.libretexts.org\/Core\/Organic_Chemistry\/Reactions\/Elimination_Reactions\/E1_Reactions\/Carbocation_Rearrangements\" rel=\"internal\">carbocation <\/a>is formed, water bonds with the carbocation to form a 1\u00ba, 2\u00ba, or 3\u00ba alcohol on the alkane.<\/p>\n<div id=\"section_1\">\n<h3 class=\"editable\">What Is Electrophilic Hydration?<\/h3>\n<p>Electrophilic\u00a0hydration\u00a0is the reverse <a class=\"internal mt-disabled\" title=\"Wikitexts\/UCD Chem 118B\/Chem 118B Topics\/Alkenes by Dehydration of Alcohols\" rel=\"broken\">dehydration of alcohols<\/a> and has practical application in\u00a0making alcohols for fuels and reagents for other reactions. The basic reaction under certain temperatures (given below) is the following:<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/1348\/Basic_Electrophilic_Hydration.bmp?revision=1&amp;size=bestfit&amp;width=521&amp;height=122#fixme\" alt=\"Basic Electrophilic Hydration.bmp\" width=\"521px\" height=\"122px\" \/><\/p>\n<p>The phrase &#8220;electrophilic&#8221;\u00a0literally means &#8220;electron loving&#8221;\u00a0(whereas &#8220;nucleophilic&#8221; means &#8220;nucleus loving&#8221;). Electrophilic hydrogen is essentially a proton: a hydrogen atom stripped of its electrons. Electrophilic hydrogen is commonly used to help break double bonds or restore catalysts (see <a title=\"Organic Chemistry\/Reactions\/SN2 Reaction\" href=\"https:\/\/chem.libretexts.org\/Core\/Organic_Chemistry\/Reactions\/Substitution_Reactions\/SN2\" rel=\"internal\">S<sub>N<\/sub>2<\/a> for more details).<\/p>\n<\/div>\n<div id=\"section_2\">\n<h3 class=\"editable\">How Does Electrophilic Hydration Work?<\/h3>\n<div id=\"section_3\">\n<h4 class=\"editable\">Mechanism for 3\u00ba Alcohol (1\u00ba and 2\u00ba mechanisms are similar):<\/h4>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05142003\/Electrophilic_Hydration_Mechanism.jpg\" alt=\"Electrophilic Hydration Mechanism.jpg\" width=\"692px\" height=\"303px\" \/><\/p>\n<\/div>\n<div id=\"section_4\">\n<h4 class=\"editable\">Temperatures for Types of Alcohol Synthesis<\/h4>\n<p>Heat is used to catalyze electrophilic hydration;\u00a0because the reaction is in equilibrium with the dehydration of an alcohol, which requires higher temperatures to form an alkene, lower temperatures are required to form an alcohol.\u00a0<em>The exact temperatures used are highly variable and depend on the product being formed.<\/em><\/p>\n<ul>\n<li>Primary Alcohol:\u00a0 Less than 170\u00baC<\/li>\n<li>Secondary Alcohol:\u00a0 Less than 100\u00baC<\/li>\n<li>Tertiary Alcohol:\u00a0 Less than 25\u00baC<\/li>\n<\/ul>\n<\/div>\n<div id=\"section_5\">\n<h4 class=\"editable\">But&#8230;Why Does Electrophilic Hydration Work?<\/h4>\n<ul>\n<li>An alkene placed in an aqueous non-nucleophilic strong acid immediately &#8220;reaches out&#8221; with its double bond and attacks one of the acid&#8217;s hydrogen atoms\u00a0(meanwhile, the bond between oxygen and hydrogen performs heterolytic cleavage toward\u00a0the oxygen\u2014in other words, both electrons from the oxygen\/hydrogen single bond move onto the oxygen atom).<\/li>\n<li>A carbocation is formed on the original alkene (now alkane) in the more-substituted position, where the oxygen end of water attacks with its 4 non-bonded valence electrons (oxygen has 6 total valence electrons because it is found in Group 6 on the periodic table and the second row down: two electrons in a 2s-orbital and four in 2p-orbitals. Oxygen donates one valence electron to each bond it forms, leaving four\u00a04 non-bonded valence electrons).<\/li>\n<li>After the blue oxygen atom forms its third bond with the more-substituted carbon, it develops a positive charge (3 bonds and 2 valence electrons give the blue oxygen atom\u00a0a formal charge of +1).<\/li>\n<li>The bond between the green hydrogen and the blue oxygen undergoes heterolytic cleavage, and both the electrons from the bond move onto the blue oxygen.\u00a0 The now negatively-charged strong acid picks up the green electrophilic hydrogen.<\/li>\n<li>Now that the reaction is complete, the non-nucleophilic strong acid is regenerated as a catalyst and an alcohol forms on the most\u00a0substituted carbon of the current alkane. At lower temperatures, more alcohol product can be formed.<\/li>\n<\/ul>\n<\/div>\n<div id=\"section_6\">\n<h4 class=\"editable\">What is Regiochemistry and How Does It Apply?<\/h4>\n<p>Regiochemistry deals with where the substituent bonds on the product. <strong>Zaitsev<\/strong>&#8216;s and <strong><a title=\"Organic Chemistry\/Conjugation\/Electrophilic Attack on Conjugated Dienes\/Markovnikov Addition\" href=\"https:\/\/chem.libretexts.org\/Core\/Organic_Chemistry\/Conjugation\/Electrophilic_Attack_on_Conjugated_Dienes\/Markovnikov_Addition\" rel=\"internal\">Markovnikov<\/a><\/strong>&#8216;s rules address regiochemistry, but Zaitsev&#8217;s\u00a0rule applies when synthesizing an alkene while Markovnikov&#8217;s\u00a0rule describes where the substituent bonds\u00a0onto the product. In the case of\u00a0electrophilic hydration, Markovnikov&#8217;s\u00a0rule is the only rule that <em>directly<\/em> applies. See the following for an in-depth explanation of regiochemistry Markovnikov explanation: <a class=\"internal mt-disabled\" title=\"Wikitexts\/UCD Chem 118B\/Chem 118B Topics\/Radical Additions--Anti-Markovnikov Product Formation\" rel=\"broken\">Radical Additions&#8211;Anti-Markovnikov Product Formation<\/a><\/p>\n<p>In the mechanism for a 3\u00ba alcohol shown above, the red H is added to the least-substituted carbon\u00a0connected to the nucleophilic double bonds (it has less carbons attached to it).\u00a0This means that the carbocation forms on the 3\u00ba carbon, causing it to be highly stabilized by <em>hyperconjugation<\/em><em>\u2014<\/em>electrons in nearby sigma (single) bonds help fill the empty p-orbital of the carbocation, which lessens the positive charge.\u00a0More substitution on a carbon means more sigma bonds are available to &#8220;help out&#8221; (by using overlap) with the positive charge, which creates greater\u00a0<em>carbocation stability<\/em>.\u00a0In other words,\u00a0<strong>carbocations\u00a0form on the most substituted carbon<\/strong>\u00a0connected to the double bond. Carbocations are also stabilized by resonance, but resonance is not a large factor in this case because any carbon-carbon double bonds are used to initiate the reaction, and other double bonded molecules can cause a completely different reaction.<\/p>\n<p>If the carbocation does originally form on the less substituted part of the alkene, carbocation rearrangements occur to form more substituted products:<\/p>\n<ul>\n<li><strong>Hydride shifts:<\/strong>\u00a0a hydrogen atom bonded to a carbon atom next to the carbocation\u00a0leaves that carbon to bond with the carbocation (after the hydrogen has taken both electrons from the single bond, it is known as a hydride).\u00a0This changes the once neighboring carbon to a carbocation, and the former carbocation becomes a neighboring carbon atom.<\/li>\n<\/ul>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/1350\/Hydride_Shift.bmp?revision=1&amp;size=bestfit&amp;width=415&amp;height=111#fixme\" alt=\"Hydride Shift.bmp\" width=\"415px\" height=\"111px\" \/><\/p>\n<ul>\n<li><strong>Alkyl shifts:<\/strong>\u00a0 if\u00a0no hydrogen atoms are\u00a0available for a hydride shift, an entire methyl group performs the same shift.<\/li>\n<\/ul>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/1347\/Alkyl_Shift.bmp?revision=1&amp;size=bestfit&amp;width=494&amp;height=149#fixme\" alt=\"Alkyl Shift.bmp\" width=\"494px\" height=\"149px\" \/><\/p>\n<p>The nucleophile\u00a0attacks the positive charge\u00a0formed on the most substituted carbon connected to the double bond, because the nucleophile is seeking that positive charge.\u00a0In the mechanism for a 3\u00ba alcohol shown above, water is the nucleophile.\u00a0When the green H is removed from the water molecule,\u00a0the alcohol attached to the most substituted carbon. Hence, <strong>electrophilic hydration follows Markovnikov&#8217;s\u00a0rule.<\/strong><\/p>\n<\/div>\n<div id=\"section_7\">\n<h3 class=\"editable\">What is Stereochemistry and How Does It Apply?<\/h3>\n<p><strong>Stereochemistry deals with how the substituent\u00a0bonds\u00a0on the product directionally<\/strong>. Dashes and wedges denote stereochemistry by showing whether the molecule or atom is going into or out of the plane of the board. Whenever the bond is a simple single straight line, the molecule that is bonded is equally likely to be found going into the plane of the board as it is out of the plane of the board. This indicates that\u00a0<strong>the product is a racemic mixture<\/strong>.<\/p>\n<p>Electrophilic hydration adopts a stereochemistry wherein the substituent is equally likely to bond pointing into the plane of the board as it is pointing out of the plane of the board. The 3\u00ba alcohol product could look like either of the following products:<\/p>\n<p><a title=\"Tert Alcohol Stereochemistry.bmp\" href=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/1361\/Tert_Alcohol_Stereochemistry.bmp?revision=1\" rel=\"internal\"><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/1361\/Tert_Alcohol_Stereochemistry.bmp?revision=1&amp;size=bestfit&amp;width=720&amp;height=144#fixme\" alt=\"Tert Alcohol Stereochemistry.bmp\" width=\"720px\" height=\"144px\" \/><\/a><\/p>\n<p>Note:\u00a0 Whenever a straight line is used along with dashes and wedges on the same molecule, it could be denoting that the straight line bond is in the same plane as the board. Practice with a molecular model kit and attempting the practice problems at the end can help eliminate any ambiguity.<\/p>\n<\/div>\n<div id=\"section_8\">\n<h4 class=\"editable\">Is this a Reversible Synthesis?<\/h4>\n<p>Electrophilic hydration is reversible because an alkene in water is in equilibrium with the alcohol product.\u00a0To sway the equilibrium one way or another, the temperature or the concentration of the non-nucleophilic\u00a0strong acid\u00a0can be changed. For example:<\/p>\n<ul>\n<li>Less sulfuric or phosphoric acid and an excess of water help synthesize more alcohol product.<\/li>\n<li>Lower temperatures help synthesize more alcohol product.<\/li>\n<\/ul>\n<\/div>\n<div id=\"section_9\">\n<h4 class=\"editable\">Is There a Better Way to Add Water to Synthesize an Alcohol From an Alkene?<\/h4>\n<p>A more efficient pathway does exist: see <a class=\"internal mt-disabled\" title=\"Wikitexts\/UCD Chem 118B\/Chem 118B Topics\/Oxymercuration - Demercuration\" rel=\"broken\">Oxymercuration &#8211; Demercuration: A Special Electrophilic Addition<\/a>.\u00a0\u00a0Oxymercuration does not allow for rearrangements, but it does require the use of mercury, which is highly toxic. Detractions for using electrophilic hydration to make alcohols include:<\/p>\n<ul>\n<li>Allowing for carbocation rearrangements<\/li>\n<li>Poor yields due to the reactants and products being in equilibrium<\/li>\n<li>Allowing for product mixtures (such as an (R)-enantiomer and an (S)-enantiomer)<\/li>\n<li>Using sulfuric or phosphoric acid<\/li>\n<\/ul>\n<p>Oxymercuration is a special electrophilic addition. It is anti-stereospecific and regioselective. Regioselectivity is a process in which the substituents choses one direction it prefers to be attached to over all the other possible directions. The good thing about this reaction is that there are no <a title=\"Carbocation Rearrangements\" href=\"https:\/\/chem.libretexts.org\/Core\/Organic_Chemistry\/Reactions\/Elimination_Reactions\/E1_Reactions\/Carbocation_Rearrangements\" rel=\"internal\">carbocation rearrangement<\/a> due to stabilization of the reactive intermediate. Similar stabilization is also seen in <a title=\"The Reaction with Bromine\" href=\"https:\/\/chem.libretexts.org\/Core\/Organic_Chemistry\/Reactions\/Addition_Reactions\/Electrophilic_Addition_Reactions\/Reactions_of_Alkenes_with_Bromine\" rel=\"internal\">bromination <\/a>addition to alkenes.<\/p>\n<\/div>\n<\/div>\n<div id=\"section_10\">\n<h3 class=\"editable\">Introduction<\/h3>\n<p>Carbocation rearrangement is a process in which the carbocation intermediate can form a more stable ion. With <a class=\"internal\" title=\"Organic Chemistry\/Reactions\/E1 Reaction\/Carbocation Rearrangements\" href=\"https:\/\/chem.libretexts.org\/Core\/Organic_Chemistry\/Reactions\/Elimination_Reactions\/E1_Reactions\/Carbocation_Rearrangements\" rel=\"internal\">carbocation rearrangement<\/a>, the reaction would not be able to hydrate quickly under mild conditions and be produced in high yields. This reaction is very fast and proceeds with 90% yield.<\/p>\n<p><img decoding=\"async\" src=\"https:\/\/chem.libretexts.org\/LibreTexts\/Athabasca_University\/Chemistry_350%3A_Organic_Chemistry_I\/Chapter_8%3A_Alkenes%3A_Reactions_and_Synthesis\/denied:data:image\/png;base64,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#fixme\" alt=\"\" \/><\/p>\n<p>This reaction involves a mercury acting as a reagent attacking the alkene double bond to form a <em>Mercurinium Ion Bridge<\/em>. A water molecule will then attack the most substituted carbon to open the mercurium ion bridge, followed by proton transfer to solvent water molecule.<\/p>\n<p><img decoding=\"async\" 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alt=\"\" \/><\/p>\n<p>The organomercury intermediate is then reduced by sodium borohydride &#8211; the mechanism for this final step is beyond the scope of our discussion here. Notice that overall, the oxymercuration &#8211; demercuration mechanism follows <a title=\"Regioselectivity and the Markovnikov Rule\" rel=\"broken\">Markovnikov&#8217;s Regioselectivity<\/a> with the OH group is attached to the most substituted carbon and the H is attach to the least substituted carbon. The reaction is useful, however, because strong acids are not required, and carbocation rearrangements are avoided because no discreet carbocation intermediate forms.<\/p>\n<\/div>\n<div id=\"section_11\">\n<h3 class=\"editable\">References<\/h3>\n<ol>\n<li>Vollhardt, K. Peter C. Organic chemistry structure and function. New York: W.H. Freeman, 2007.<\/li>\n<li>Smith, Michael B., and Jerry March. March&#8217;s Advanced Organic Chemistry Reactions, Mechanisms, and Structure (March&#8217;s Advanced Organic Chemistry). New York: Wiley-Interscience, 2007 2007.<\/li>\n<li><a class=\"external\" title=\"http:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00435a033\" href=\"http:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00435a033\" target=\"_blank\" rel=\"external nofollow noopener\">Roderic P. Quirk , <\/a><a class=\"external\" href=\"http:\/\/pubs.acs.org\/action\/doSearch?ContribStored=Lea%2C+Robert+E.\" target=\"_blank\" rel=\"external nofollow noopener\">Robert E. <\/a><a class=\"external\" title=\"http:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00435a033\" href=\"http:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00435a033\" target=\"_blank\" rel=\"external nofollow noopener\">Lea, Reductive demercuration of hex-5-enyl-1-mercuric bromide by metal hydrides. Rearrangement, isotope effects, and mechanism<\/a><a class=\"external\" href=\"http:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00435a033\" target=\"_blank\" rel=\"external nofollow noopener\">, <\/a><a class=\"external\" title=\"http:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00435a033\" href=\"http:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00435a033\" target=\"_blank\" rel=\"external nofollow noopener\"><cite>J. Am. Chem. Soc.<\/cite>, 1976, 98 (19), pp 5973\u20135978<\/a>.<\/li>\n<\/ol>\n<\/div>\n<div id=\"section_12\">\n<div class=\"textbox examples\">\n<h3>Examples<\/h3>\n<div id=\"section_12\">\n<h3 class=\"editable\">Problem<\/h3>\n<p>What are the end products of these reactants?<img decoding=\"async\" class=\"aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/127217\/8-4_Question.jpg?revision=1\" alt=\"8-4 Question.jpg\" \/><\/p>\n<p><img decoding=\"async\" src=\"https:\/\/chem.libretexts.org\/LibreTexts\/Athabasca_University\/Chemistry_350%3A_Organic_Chemistry_I\/Chapter_8%3A_Alkenes%3A_Reactions_and_Synthesis\/denied:data:image\/png;base64,iVBORw0KGgoAAAANSUhEUgAAAfkAAAINCAIAAACyP5EhAAAgAElEQVR4nO3dT6gzV93A8UCav\/dx10pFwVFBBmk1grRZFAkiGHQTXEhAhKdFIUWECAUDBbMzOyOCBHRRECEryUIluArYRaCb4CrLdDfLWc4y7yKv07nJzMmZmTP\/fvl+Vk9v5s6c3Mx8Mzkz97Z2BgBIVyt6AACAzNF6AJCP1gOAfLQeAOSj9QAgH60HAPloPQDIR+sBQD5aDwDy0XoAkI\/WA4B8tB4A5KP1ACAfrQcA+Wg9AMhH6wFAPloPAPLRegCQj9YDgHy0HgDko\/UAIB+tBwD5aD0AyEfrAUA+Wg8A8tF6AJCP1gOAfLQeAOSj9QAgH60HAPloPQDIR+sBQD5ab9LpdCp6CAAQgtYbs9vtBoNB0aMAgBC03hhaD6C0aL0xtB5AadF6Y2g9gNKi9cbQegClReuNofUASovWG0Prq6hWizwEEjyk+Ja7S9YCYn2jqYXjrkRn5ZpPCjngBTCG1ldO4rCmbH1o6PXXn3PuEz9ZzSeFfPDTN4bWV4tON\/Npfeh3Kb5YidbrPynkgx+9MbS+QvzoZNr64PRF8KGof9\/dirr1obMlhbQ+2UPIVLY\/94d6yWl9FcWdiFB\/lyLoUe8u+seI+h1C8WjKY43Wy5Dhz93sVabyo\/VVlLj1UaK+K9PWax5ooSf+d+k82avV0voSyurnrv6wGVxGDFpfRRmd15ew9ZotvjsMndXS+hLK5Oeu85LffbRyaH0VVaX1itNq9UrUg9Fx98nefkVe6190nzqtdrPR8H\/4zUaj3Wo9dbpFD01XYfP1mgtUCK2vogq1Ptaj6k3Q+lg6rbZiIqvVbL7oPhU9xvtovTG0vooKb73mJgy2Pu5Bp9l6na1U8XhvNZuK0F\/U6\/WnbtlP8Gm9MbS+ijJq\/e2\/1ee8Cbqp3pzOYpribl1nGFXRaX92Rt9sNLrtjv\/QU6cbfBtoNhoFjlMHrTeG1ldRsvNl\/VNdv\/I6ZQwun3Jzocvk9iHmdkhVPNJfdJ\/8wbdbrdBluu2Ov0zwnaCEaL0xtF4eg\/tnypPr9Nu9mnZQLxxr\/ZUOuoLf8cYrrygWa7dal8VazWZuY0uA1htD6+VJvH+qpy8Kab3xhcXzp2jUJ+zB0\/\/cxpYArTeG1guTcudUn+3ms+cXcnztdrv8N5qFer1+efnu3mZD61PdPFA5f\/\/732k9HpzjOH745vP5brfzPK\/oQWXLP6+v1+tFj0WlyNqKaf1ut+v1er\/+9a9pPeC6bu3GBx98sN1uRXbfv1cn6vptSdD6VBzHGY1Gg8HgcDjsdrvvfOc7RY3kk08++fTTT4va+vF4LGrTsTiO026rfi8GWSt6FzAseB9OyX+HtrAffdVfdc\/z5vO5ZVmbzebylU8\/\/fSNN94YjUan0ynPkbiuO5vNvvrVr37ta19bLBY5nzodDofBYDCZTPLcKMrsdDp9+ctffrTQd1rtoodzh7Sffj7W67VlWfP5\/Cqsruv+9re\/tW17Npu5rpvDSFarlW3bl8Rfom\/btv\/2kynHcSaTSa\/XE3MtDuk5jvPqq68K7rsvGPry\/yLVmdbHtd\/v+\/3+eDx2HOfqoeVyaVnWer32PG+xWNi2vVqtshvJ5SLBZDK5GsnpdPKnlTLadD5PEBV1e2jIU7nQn2m9PsdxxuNxv9\/f7\/dXD12yO51Og+fy\/mnv7fLpR3K35v47gfGPF9vtNs8PLkDZPHW6lQv9mdbr8E9j1+v11UN3T6IPh0PU54BkI7m6SKC2Wq0sy1oul+k3fT6fj8fjcDgcDoc5X5AASsW\/775CoT\/T+rs2m03oaWysyfGo+f1Ykq3Edd3pdGrb9na7TbxpIyspobvTyorp5gTfErrd0DGkWTkypfmHE0qIXSfS5Q6T0Ptq1uu1f0VUc23+Kfnth4O7FBcJNPmn5AlujrxchzD14aA8dNqqeCjqHUKz9cnGQ+sLp\/mHE0qIXSeE67pRd5ikzK4\/6a954VRxkSCBuFPtl+WvrkPIcBvNuHmt3fz1SvXysbZF60vL\/xBW\/j9Yf4Vd59rlNPb2DhOD2d3v96G30AQpLhKkpHMLzeU6RLLPARWVUeuTTdHQ+tKq7r2k1RtxdqJOYzPKbvDW+KuHoi4SmKK4NT7nm\/TLI+40TlSXFU1Xp5w5nEqg9RJMJpPb09hMs3sbVsVFAuNut6V4+5FNfejGSrMi6MGHFBdmoxYIXez+cwPO5zOtV8gtu5cJk+9+97s\/\/elP8\/811Mub2bvvvnt3WkmwLFp\/tXCw1EbO6yt6domiVHJfSfMJV3GW5LvcYphzdtfr9W9+85vcNhfked5kMvnPf\/5TyNYLd3e3uZvmc8TpfFTi7+7AmgvQeuir5L6SuPWKj9W+y23s8m4xRCjN8wOdL171Vz2Ho94QrS8t9WlimVVvxOekrdf8ru12K+8WQ4TSPGLL1vq7iyE7tD5XCVpfxdcGmdLfJTRbf34+h347yWNqvl5nHhIZqe6PvXojPtN6pFYLE3w09N9Xa7j79auVB1uv2Lr+Rtmroa+S+0rooXJ13qQ4egF9Zd5zyjw2lE0l95W7n3Bvl+SoQDLsOZChkvux\/sdqWo802G0gRiV3ZVoPALFUsoDJrlwluKILADJUMnOat0DofCOhB\/AIKlm6u61X33wZdaMbAEglMHbUHACukEIAkI\/WA4B8tB4A5KP1ACAfrQcA+Wg9AMhH6wFAPloPAPLRegCQj9YDgHy0HgDko\/UAIB+tBwD5aD0AyEfrAUA+Wg8A8tF6AJCP1gOAfLQeAOSj9QAgH60HAPloPQDIR+sBQD5aDwDy0XoAkI\/WA4B8tB4A5KP1ACAfrQcA+Wg9AMhH6wFAPloPAPLRegCQj9YDgHy0HgDko\/UAIB+tBwD5aD0AyEfrAUA+Wg8A8tF6AJCP1gOAfLQeAOSj9QAgH60HAPloPQDIR+sBQD5aDwDy0XoAkI\/WA4B8tB4Pp1aL3O0TPKT4lrtL1gJifaOpheOuRGflmk8KOePFwGNJHNaUrQ8Nvf76c8594ier+aSQP14JPBCdbubT+tDvUnyxEq3Xf1LIHy8DHoUfnUxbH5y+CD4U9e+7W1G3PnS2pJDWJ3sIucnkNbg7YcdrjwLFnYhQf5ci6FHvLvpZVL9DKB5NeYjRennMvwaJz1+AfCRufZSo78q09ZqfTtRnXYpvv\/tkr1ZbrYP9Rfep02o3Gw3\/iTQbjXar9dTpFj20rBh+DdSnHjpfB7KW0Xl9CVuv2eK7w9BZbYVa32m1FW9mrWbzRfep6DGal\/lrQOtRNlVpveK0Wr0S9WB06B+2lWt9q9lUhP6iXq8\/daWd4BfWevVDRTkej57nFT0KZKtCrY\/1qHoTtP58Pnfan53RNxuNbrvjP\/TU6QbfBpqNRoHjzEK2r0Hc3bFwi8XCtu3NZlP0QJChwluvuQmDrY97rGm2Xmcr5TnMX3Sf\/JS3W63QZbrtjr9M8J1AAFp\/7XQ6jUajwWBwOByKHgsykVHrb\/+tPudN0E315nQW0xR36zrDKJzf8cYrrygWa7dal8VazWZuY8tBhq9EsiMqT5vN5gtf+MJbb711m\/Xdbtfr9SaTieu6WWzadd3ZbPbqq6\/OZrOMNqFwOBzeeuutL3zhC4V8glmtVrZt5\/+sfcnOl\/VPdf3K65QxuHzKzYUuk9uHmNshFX6AX\/GnaNQn7MHT\/9zGloOsnozOj6nAH+XhcBgMBqPR6HQ6+Vl3HOdqsdVqZVnWcrk0u\/VL7BaLheu6l1mj1WpldhNRHMeZTCa9Xm+32+X\/CUbxoy4Pg7tlypPr9NutPadeONb6Sxt0hXq9fhnw3dtsKvfUdGTyZDR\/RoX8KIOxC37d7+\/VtVnXdafTqW3b2+02\/dZDYxc1JLM8zwt9X8mnvxWaGUu8W6qnLwppvfGFH4F\/Xl+v14sei0nmX2b9XSf\/nWy5XCpOoi\/zKqFZPx6Pw+FwOByeTqdkm74bO\/+jRhbN3Ww2tm0r5ov8tzrjm\/Z\/qpW44p1yn1Sf7eazw9PulPx7daKu31aU4d2iFib4aOi\/c7Ddbm3bnk6nd6eJT6fTJevH4zF0JXFn2D3Pm8\/nmrHbbDaWZc3nc1O3fl7epS6zVeolFW91ia3X69BPSxDmZz\/7Wa1W++EPf7harW4PnAoJ3ocj7HdoCzsFyK31\/il5rF0w6r0haiYkynq9jtvuy3uDZVnr9Vp\/wLeSzT4l+3Hd2u\/3\/X5\/PB6XeWoepnied3WGV8XuB0PfabWLHo5hklt\/OVHt9XqJT1SXy2XotVl\/hl0x+5wydo7jjMfjfr+\/3+8TfHvUyDXpfwy6lXLkWRgMBqGfOJGPSnyqC4Ze3i9SnYtqfS370Edda41LcXZ8OBxCp2UMxi7BG0aaTF+J+4Zh6hMJquivf\/3r5z73udDWFz20+8SH\/lzgeX12srixRHPW25\/hMRs7zVnvy+Xf9NMvQZe3Op17hC6Xfw1eaUCFfPjhh5Xru++p0xUf+rOw1l9OqLO7sU99N8vde13SUN\/NkvW9LsFfR4j7KB7B8XisVt+D\/PvuBYf+LKb1uc0ehF6bzS12oTdumpqtuuv2zSyf3wwAsqP5hxMEkND6BPe6pOQ37p\/\/\/Gf+sfMnqf7xj3\/k\/Guo\/lvdn\/\/855x\/4xfIguYfThCg8q0\/Ho8vX74s5Ma+w+Hw5ptv\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#fixme\" alt=\"\" \/><\/p>\n<\/div>\n<div id=\"section_13\">\n<h3 class=\"editable\">Answer<\/h3>\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q345958\">Show Answer<\/span><\/p>\n<div id=\"q345958\" class=\"hidden-answer\" style=\"display: none\">\n<p><img decoding=\"async\" class=\"aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/127215\/8-4_Answer.jpg?revision=1\" alt=\"8-4 Answer.jpg\" \/>The end product to these practice problems are pretty much very similar. First, you locate where the double bond is on the reactant side. Then, you look at what substituents are attached to each side of the double bond and add the OH group to the more substituent side and the hydrogen on the less substituent side.<\/div>\n<\/div>\n<p>&nbsp;<\/p>\n<\/div>\n<div id=\"section_14\">\n<h3 class=\"editable\">Problems<\/h3>\n<p>Predict the product of each reaction.<\/p>\n<p>1)<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/1352\/PP1_Q_(1).bmp?revision=1&amp;size=bestfit&amp;width=326&amp;height=100#fixme\" alt=\"PP1 Q (1).bmp\" width=\"326px\" height=\"100px\" \/><\/p>\n<p>2)\u00a0 How does the\u00a0cyclopropane group affect the reaction?<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/1354\/PP2_Q.bmp?revision=1&amp;size=bestfit&amp;width=307&amp;height=136#fixme\" alt=\"PP2 Q.bmp\" width=\"307px\" height=\"136px\" \/><\/p>\n<p>3)\u00a0\u00a0 (Hint: What is different about this problem?)<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/1356\/PP3_Q.bmp?revision=1&amp;size=bestfit&amp;width=280&amp;height=174#fixme\" alt=\"PP3 Q.bmp\" width=\"280px\" height=\"174px\" \/><\/p>\n<p>4)\u00a0\u00a0\u00a0 (Hint: Consider\u00a0stereochemistry.)<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/1358\/PP4_Q.bmp?revision=1&amp;size=bestfit&amp;width=450&amp;height=111#fixme\" alt=\"PP4 Q.bmp\" width=\"450px\" height=\"111px\" \/><\/p>\n<p>5)\u00a0 Indicate any shifts as well as the major product:<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/1360\/PP5_Q.bmp?revision=1&amp;size=bestfit&amp;width=425&amp;height=201#fixme\" alt=\"PP5 Q.bmp\" width=\"425px\" height=\"201px\" \/><\/p>\n<p>&nbsp;<\/p>\n<\/div>\n<div id=\"section_15\">\n<h3 class=\"editable\">Answers to Practice Problems<\/h3>\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q154724\">Show Answer<\/span><\/p>\n<div id=\"q154724\" class=\"hidden-answer\" style=\"display: none\">\n<p>1)\u00a0 This is a basic electrophilic hydration.<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/1351\/PP1_A.bmp?revision=1&amp;size=bestfit&amp;width=275&amp;height=157#fixme\" alt=\"PP1 A.bmp\" width=\"275px\" height=\"157px\" \/><\/p>\n<p>2)\u00a0The answer is additional side products, but the major product formed is still the same (the product shown).\u00a0 Depending on the temperatures used, the cyclopropane may open up into a straight chain, which makes it unlikely that the major product will form (after the reaction, it is unlikely that the 3\u00ba carbon will remain as such).<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/1353\/PP2_A.bmp?revision=1&amp;size=bestfit&amp;width=213&amp;height=135#fixme\" alt=\"PP2 A.bmp\" width=\"213px\" height=\"135px\" \/><\/p>\n<p>3)\u00a0A hydride shift actually occurs from the top of the 1-methylcyclopentane to where the carbocation had formed.<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/1355\/PP3_A_(1).bmp?revision=1&amp;size=bestfit&amp;width=290&amp;height=201#fixme\" alt=\"PP3 A (1).bmp\" width=\"290px\" height=\"201px\" \/><\/p>\n<p>4)\u00a0 This reaction will\u00a0have poor yields due to a very unstable intermediate.\u00a0 For a brief moment, carbocations can form on the two center carbons, which are more stable than the outer two carbons.\u00a0 The carbocations have an sp2 hybridization, and when the water is added on, the carbons change their hybridization to sp3.\u00a0 This makes the methyl and alcohol groups equally likely to be found going into or out of the plane of the paper- the product is racemic.<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/1357\/PP4_A.bmp?revision=1&amp;size=bestfit&amp;width=343&amp;height=115#fixme\" alt=\"PP4 A.bmp\" width=\"343px\" height=\"115px\" \/><\/p>\n<p>5) In the first picture shown below, an alkyl shift occurs but a hydride shift (which occurs faster) is possible.\u00a0\u00a0 Why doesn&#8217;t a hydride shift occur?\u00a0 The answer is because the alkyl shift leads to a more stable product.\u00a0 There is a noticeable amount of side product that forms where the two methyl groups are, but the major product shown below is still the most significant due to the hyperconjugation that occurs by being in between the two cyclohexanes.<\/p>\n<p><a title=\"PP5 A.bmp\" href=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/1359\/PP5_A.bmp?revision=1\" rel=\"internal\"><img decoding=\"async\" class=\"internal default\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/1359\/PP5_A.bmp?revision=1&amp;size=bestfit&amp;width=720&amp;height=164#fixme\" alt=\"PP5 A.bmp\" width=\"720px\" height=\"164px\" \/><\/a><\/p>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_16\">\n<div class=\"textbox exercises\">\n<h3>Exercises<\/h3>\n<div id=\"section_16\">\n<div id=\"s61713\">\n<div>\n<h3 id=\"Questions-61713\">Questions<\/h3>\n<p><strong>1.<\/strong><\/p>\n<p>In each case, predict the product(s) of these reactants of oxymercuration.<\/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\/05142007\/8-4qu.png\" alt=\"\" width=\"333\" height=\"199\" \/><\/p>\n<p><strong>2.<\/strong><\/p>\n<p>Propose the alkene that was the reactant for each of these products of oxymercuration.<\/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\/05142009\/8-4-2qu.png\" alt=\"\" width=\"209\" height=\"240\" \/><\/p>\n<\/div>\n<div id=\"section_17\">\n<h3 id=\"Solutions-61713\">Solutions<\/h3>\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q377863\">Show Answer<\/span><\/p>\n<div id=\"q377863\" class=\"hidden-answer\" style=\"display: none\">\n<p><strong>1.<\/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\/05142011\/8-4sol.png\" alt=\"\" width=\"532\" height=\"233\" \/><\/p>\n<p><strong>2.<\/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\/05142014\/8.42.png\" alt=\"\" width=\"475\" height=\"231\" \/><\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div><\/div>\n<\/div>\n<\/div>\n<div>\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>Lance Peery (UCD), Duyen Dao-Tran<\/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>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":3,"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-1077","chapter","type-chapter","status-publish","hentry"],"part":24,"_links":{"self":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/1077","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters"}],"about":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/types\/chapter"}],"author":[{"embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/users\/44985"}],"version-history":[{"count":5,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/1077\/revisions"}],"predecessor-version":[{"id":2299,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/1077\/revisions\/2299"}],"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\/1077\/metadata\/"}],"wp:attachment":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/media?parent=1077"}],"wp:term":[{"taxonomy":"chapter-type","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapter-type?post=1077"},{"taxonomy":"contributor","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/contributor?post=1077"},{"taxonomy":"license","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/license?post=1077"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}