{"id":35488,"date":"2023-09-15T15:00:04","date_gmt":"2023-09-15T20:00:04","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=35488"},"modified":"2025-12-12T03:41:55","modified_gmt":"2025-12-12T09:41:55","slug":"hydration-alkenes-acid","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2023\/09\/15\/hydration-alkenes-acid\/","title":{"rendered":"Hydration of Alkenes With Aqueous Acid"},"content":{"rendered":"<p><strong>Hydration of Alkenes to Give Alcohols<\/strong><\/p>\n<ul>\n<li>When alkenes are treated with aqueous acid (H<sub>3<\/sub>O+) they can be converted to alcohols.<\/li>\n<li>Formation of the new C-OH bond tends to occur on the\u00a0<strong>most substituted\u00a0<\/strong>carbon of the alkene (&#8220;Markovnikov&#8221; regioselectivity) and is\u00a0<strong>not\u00a0<\/strong>stereoselective &#8211; a mixture of\u00a0<em>syn<\/em> and\u00a0<em>anti<\/em> addition occurs.<\/li>\n<li>The reaction proceeds through a carbocation intermediate. Protonation of the alkene occurs such that the most stable carbocation is formed.<\/li>\n<li>Hydration with acid can be accompanied by rearrangements if a more stable carbocation intermediate can be formed through a hydride or alkyl shift. To avoid this, oxymercuration of alkenes is an alternative that does not give rearrangement. (<span style=\"color: #993366;\"><em>See article &#8211; <a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2023\/08\/31\/oxymercuration-demercuration\/\">Oxymercuration of Alkenes<\/a><\/em><\/span>)<\/li>\n<li>Alcohols will also add to alkenes in the presence of acid. If an alkene and acid are present on the same molecule,\u00a0<strong>intramolecular\u00a0<\/strong>addition can occur.<\/li>\n<li>Anti-Markovnikov alcohols can be obtained through\u00a0<strong>hydroboration\u00a0<\/strong>(<span style=\"color: #993366;\"><em>See ar<span style=\"color: #993366;\">ticle &#8211; <a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2013\/03\/28\/hydroboration-of-alkenes-the-mechanism\/\">Hydroboration-Oxidation of Alcohols<\/a><\/span><\/em><\/span>)<\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-35543\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/09\/0-summary-of-Acid-catalyzed-hydration-of-alkenes-to-give-alcohols-and-addition-of-alcohols-to-give-ethers-2.gif\" alt=\"summary of Acid catalyzed hydration of alkenes to give alcohols and addition of alcohols to give ethers \" width=\"640\" height=\"631\" \/><\/a><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li style=\"list-style-type: none;\">\n<ol>\n<li><a href=\"#one\">Hydration of Alkenes With Acid<\/a><\/li>\n<li><a href=\"#two\">Acid-Catalyzed Hydration of Alkenes Has Markovnikov Regioselectivity<\/a><\/li>\n<li><a href=\"#three\">Hydration Is Not Stereoselective<\/a><\/li>\n<li><a href=\"#four\">Mechanism for the Acid-Catalyzed Hydration of Alkenes<\/a><\/li>\n<li><a href=\"#five\">Reaction Energy Diagram<\/a><\/li>\n<li><a href=\"#six\">Carbocation Rearrangements in Hydration<\/a><\/li>\n<li><a href=\"#seven\">Addition of Alcohols To Alkenes With Acid<\/a><\/li>\n<li><a href=\"#eight\">Intramolecular Reactions of Alkenes and Alcohols<\/a><\/li>\n<li><a href=\"#nine\">Summary<\/a><\/li>\n<li><a href=\"#notes\">Notes<\/a><\/li>\n<li><a href=\"#quiz\">Quiz Yourself!<\/a><\/li>\n<li><a href=\"#references\">(Advanced) References and Further Reading<\/a><\/li>\n<\/ol>\n<\/li>\n<\/ol>\n<hr \/>\n<h2><a id=\"one\"><\/a>1. Hydration of Alkenes With Acid<\/h2>\n<p>When <strong>alkenes<\/strong> (olefins) are treated with strong <strong>aqueous<\/strong> <strong>acid<\/strong> (H<sub>3<\/sub>O<sup>+<\/sup>)\u00a0they undergo net <strong>addition<\/strong> of water across the double bond (&#8220;hydration&#8221;). A new C-H bond and and a new C-OH bond are formed, and the C-C pi bond is broken.<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-35511\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/09\/1-acid-catalyzed-hydration-of-alkenes-to-give-markovnikov-alcohols-overview-using-h3O.gif\" alt=\"acid catalyzed hydration of alkenes to give markovnikov alcohols overview using h3O\" width=\"600\" height=\"434\" \/><\/a><\/p>\n<p>If we add up the bond dissociation energies (BDE&#8217;s) of the bonds that <strong>form<\/strong> (C-H, about 98 kcal\/mol, and C-O about 85 kcal\/mol) and subtract their sum from those of the bonds that <strong>break<\/strong> (C-C pi, about 63 kcal\/mol, and H-O, about 111 kcal\/mol) the reaction is <strong>exothermic by about 10 kcal\/mol<\/strong> for the addition of H<sub>2<\/sub>O. [<span style=\"color: #993366;\"><em><a style=\"color: #993366;\" href=\"https:\/\/www2.chemistry.msu.edu\/faculty\/reusch\/OrgPage\/bndenrgy.htm\">Link to useful table<\/a><\/em><\/span>]<\/p>\n<p>H<sub>2<\/sub>O will not add to alkenes by itself, however. Strong acid is required. The reagent for this reaction is commonly written as &#8220;H<sub>3<\/sub>O+&#8221; which is often just a combination of water and sulfuric acid. <span style=\"color: #993366;\"><em>(Acids like H<sub>2<\/sub>SO<sub>4<\/sub> are used since the conjugate base, HSO<sub>4<\/sub>(-), is a poor nucleophile and will not compete with H<sub>2<\/sub>O in attack on the carbocation).<\/em><\/span> [<a href=\"#noteone\"><span style=\"color: #ff0000;\">Note 1<\/span><\/a>]<\/p>\n<p>This reaction bears many similarities to the addition of H\u2013X (HCl, HBr, HI) across alkenes in that it is <strong>regioselective<\/strong> for formation of the <strong>more substituted<\/strong> alcohol (<span style=\"color: #993366;\"><em>&#8220;Markovnikov&#8221; selectivity<\/em><\/span>) and also that carbocation rearrangements can occur (<span style=\"color: #993366;\"><em>See: <a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2013\/02\/26\/rearrangements-in-alkene-addition-reactions\/\">Rearrangements in Alkene Addition Reactions<\/a><\/em><\/span>)<\/p>\n<h2><a id=\"two\"><\/a>2. Hydration of Alkenes Has &#8220;Markovnikov&#8221; Regioselectivity<\/h2>\n<p>Any time an addition of two different atoms occurs across a double bond there is the possibility of forming constitutional isomers. Hydration of propene, for example, could result in the formation of either 1-propanol or 2-propanol.<\/p>\n<p>A <strong>regioselective<\/strong> reaction is one that shows a strong preference for the formation of one constitutional isomer (&#8220;regioisomer&#8221;) over another.<\/p>\n<p>In the addition of H<sub>2<\/sub>O across an alkene catalyzed by acid, the <strong>major <\/strong>product results from formation of the C-OH bond on the <strong>most substituted <\/strong>carbon of the alkene &#8211; that is, the sp<sup>2 <\/sup>-hybridized carbon of the alkene directly bonded to the most carbon atoms.<\/p>\n<p>This is known as &#8220;Markovnikov&#8221; <strong>regioselectivity. <\/strong>[<span style=\"color: #993366;\"><em>See article &#8211; <a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2013\/02\/11\/markovnikovs-rule-2-why-it-works\/\">Addition of HX to Alkenes and Markovnikov&#8217;s Rule<\/a><\/em><\/span>]<\/p>\n<p><span style=\"color: #993366;\"><em>[Alternatively, you can look at it as the H forms on the carbon containing the most bonds to hydrogen. A useful mnemonic here is &#8220;the rich (in C-H bonds) get richer (get another C-H bond)&#8221; ].<\/em><\/span><\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-35512\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/09\/2-hydration-of-alkenes-with-acid-is-selective-or-marknovnikov-addition-produdcts-OH-is-formed-on-most-substituted-alcohol.gif\" alt=\"hydration of alkenes with acid is selective or marknovnikov addition produdcts OH is formed on most substituted alcohol\" width=\"640\" height=\"333\" \/><\/a><\/p>\n<p>Here are some more examples of the reactions of H<sub>3<\/sub>O+ with alkenes. The major product has the C-OH bond form on the more substituted carbon in each case.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-35513\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/09\/3-some-representative-examples-of-the-acid-catalyzed-hydration-of-alkenes-to-give-marknovnikov-products.gif\" alt=\"some representative examples of the acid catalyzed hydration of alkenes to give marknovnikov products\" width=\"640\" height=\"478\" \/><\/a><\/p>\n<p>Depending on the structure of the starting alkene, the resulting product(s) may be a mixture of structural isomers, a mixture of enantiomers, diastereromers, or a single achiral product. [<span style=\"color: #993366;\"><em>For more on this topic, see <a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2012\/05\/23\/whats-a-racemic-mixture\/\">What&#8217;s A Racemic Mixture<\/a>, or <a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2018\/09\/10\/types-of-isomers\/\">Types of Isomers<\/a><\/em><\/span>]<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35493\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35493\"] {\n--wq-question-width: 100%;\n--wq-question-color: #009cff;\n--wq-question-height: auto;\n--wq-font-color: #444;\n}\n\n\t\t\t.wq-quiz-wrapper[data-id=\"35493\"] {\n\t\t\t\t--wq-question-width: 600px;\n\t\t\t}\n\n\t\t\t@media screen and (max-width: 600px) {\n\t\t\t\t.wq-quiz-wrapper[data-id=\"35493\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35493\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35493 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35493\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-fbzj8\" data-id=\"fbzj8\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2575-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2575-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper -->\n<p>See if you can determine the major product in the reaction below:<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35506\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35506\"] {\n--wq-question-width: 100%;\n--wq-question-color: #009cff;\n--wq-question-height: auto;\n--wq-font-color: #444;\n}\n\n\t\t\t.wq-quiz-wrapper[data-id=\"35506\"] {\n\t\t\t\t--wq-question-width: 600px;\n\t\t\t}\n\n\t\t\t@media screen and (max-width: 600px) {\n\t\t\t\t.wq-quiz-wrapper[data-id=\"35506\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35506\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35506 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35506\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-o6t2u\" data-id=\"o6t2u\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2576-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2576-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper -->\n<h2><a id=\"three\"><\/a>3. Acid-Catalyzed Hydration is Not Stereoselective<\/h2>\n<p>The pi bond in alkenes is <strong>flat<\/strong> and has two faces.<\/p>\n<p>When addition occurs such that both new bonds to carbon form on the <strong>same<\/strong> face of the alkene, we call this <em>syn<\/em> addition. When the two bonds are formed on <strong>opposite<\/strong> faces of the alkene, it is called <em>anti<\/em> addition.<\/p>\n<p><em>(<span style=\"color: #993366;\">&#8220;syn&#8221;-\u00a0 and &#8220;anti&#8221; are subtly different from &#8220;cis&#8221; and &#8220;trans&#8221; in that they refer to dihedral angle, as opposed to orientation about a double bond or small ring. See <\/span><a href=\"https:\/\/www.masterorganicchemistry.com\/2020\/02\/28\/staggered-vs-eclipsed-conformations-of-ethane\/\"><span style=\"color: #993366;\">Staggered vs. Eclipsed Conformations of Ethane<\/span><\/a>)<\/em><\/p>\n<p>Some reactions, like hydroboration, are stereoselective for\u00a0<em>syn<\/em> addition products. Others, like bromination of alkenes, are stereoselective for\u00a0<em>anti<\/em> addition products. <em>[<span style=\"color: #800080;\">See posts &#8211; <a style=\"color: #800080;\" href=\"https:\/\/www.masterorganicchemistry.com\/2013\/03\/28\/hydroboration-of-alkenes-the-mechanism\/\">Hydroboration of Alkenes<\/a>, <a style=\"color: #800080;\" href=\"https:\/\/www.masterorganicchemistry.com\/2013\/03\/15\/alkene-bromination-mechanism\/\">Halogenation of Alkenes<\/a><\/span>]<\/em><\/p>\n<p>In contrast, hydration of alkenes is <strong>not<\/strong> stereoselective. In the example below, the product where C-OH and C-H have added to the same face of the cyclohexane ring (&#8220;<em>syn<\/em> addition&#8221;) is formed in about <strong>equal<\/strong> proportion to the product where C-OH and C-H are formed on opposite faces of the cyclohexane ring (&#8220;<em>anti<\/em> addition&#8221;).<span style=\"color: #800080;\"> [<a style=\"color: #800080;\" href=\"#refthree\"><em>Reference<\/em><\/a>]<\/span><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-35514\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/09\/6-acid-catalyzed-hydration-of-alkenes-is-not-stereoselective-gives-roughly-equal-mixture-of-syn-and-anti-addition.gif\" alt=\"acid catalyzed hydration of alkenes is not stereoselective gives roughly equal mixture of syn and anti addition\" width=\"640\" height=\"353\" \/><\/a><\/p>\n<p><span style=\"color: #800080;\"><em>(Note also that in the products above, the syn and\u00a0anti products are each formed as a racemic mixture of enantiomers.)<\/em><\/span><\/p>\n<p>See if you can draw the products of the following reaction involving a <strong>deuterated<\/strong> alkene.<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35507\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35507\"] {\n--wq-question-width: 100%;\n--wq-question-color: #009cff;\n--wq-question-height: auto;\n--wq-font-color: #444;\n}\n\n\t\t\t.wq-quiz-wrapper[data-id=\"35507\"] {\n\t\t\t\t--wq-question-width: 600px;\n\t\t\t}\n\n\t\t\t@media screen and (max-width: 600px) {\n\t\t\t\t.wq-quiz-wrapper[data-id=\"35507\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35507\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35507 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35507\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-nqtgn\" data-id=\"nqtgn\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2577-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2577-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper -->\n<h2><a id=\"four\"><\/a>4. Mechanism of Acid-Catalyzed Hydration<\/h2>\n<p>So how does this reaction work, anyway?<\/p>\n<p>Well, any mechanism for hydration will have to explain some important observations.<\/p>\n<ul>\n<li>The high selectivity for Markovnikov products<\/li>\n<li>The lack of stereoselectivity<\/li>\n<li>The formation of products that arise from carbocation rearrangements.\u00a0 <em>More on this below<\/em>\u00a0 [<span style=\"color: #800080;\"><em>For a full discussion, see <a style=\"color: #800080;\" href=\"https:\/\/www.masterorganicchemistry.com\/2013\/02\/26\/rearrangements-in-alkene-addition-reactions\/\">Carbocation Rearrangements in Alkene Addition Reactions<\/a><\/em><\/span>]<\/li>\n<\/ul>\n<p>The best mechanistic explanation for this reaction is that it proceeds through a\u00a0<strong>carbocation intermediate<\/strong>, similar to the addition of H-X to alkenes.<\/p>\n<p>In the first step, the alkene is protonated by strong acid, giving a carbocation:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-35515\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/09\/8-mechanism-of-acid-catalyzed-hydration-addition-of-water-to-alkenes-gives-most-stable-carbocation-preferentially.gif\" alt=\"mechanism of acid catalyzed hydration addition of water to alkenes gives most stable carbocation preferentially\" width=\"640\" height=\"370\" \/><\/a><\/p>\n<p>Protonation could potentially occur on either carbon of the alkene, but protonation that results in the <strong>most stable carbocation<\/strong> will be favored.<\/p>\n<p>Since carbocations tend to increase in stability as the number of substituents are added, this helps to explain the observed Markovnikov selectivity. <em>(<span style=\"color: #800080;\">See article: <a style=\"color: #800080;\" href=\"https:\/\/www.masterorganicchemistry.com\/2011\/03\/11\/3-factors-that-stabilize-carbocations\/\">Carbocation Stability<\/a><\/span>)\u00a0<\/em><\/p>\n<p>(<span style=\"color: #993366;\"><em>More specifically, the reaction will proceed through the lowest-energy transition state, which is the one where the carbon best able to stabilize positive charge will be favored<\/em><\/span>. ]<\/p>\n<p>Carbocations are excellent Lewis acids, having only six valence electrons and an empty p-orbital. They will readily combine with the best nucleophile present in solution.<\/p>\n<p>In this case the best nucleophile is H<sub>2<\/sub>O, which adds to the carbocation to give R-OH<sub>2<\/sub>(+).<span style=\"color: #800080;\"><em> (For hydration, sulfuric acid is often used as opposed to hydrohalic acids like H-Cl or H-Br, since the conjugate base HSO<sub>4<\/sub>(-) is poor nucleophile and less likely to compete with H<sub>2<\/sub>O than Cl(-) or Br(-) )<\/em><\/span><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-35516\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/09\/9-mechanism-of-acid-catalyzed-addition-of-water-to-alkenes-addition-of-water-to-carbocation-followed-by-deprotonation.gif\" alt=\"mechanism of acid catalyzed hydration addition of water to alkenes gives most stable carbocation preferentially\" width=\"640\" height=\"330\" \/><\/a><\/p>\n<p>Deprotonation of the oxonium ion by a weak base then gives the neutral alcohol. Note that in this case, H<sub>3<\/sub>O+ is regenerated, so acid acts as a\u00a0<strong>catalyst<\/strong> here.<\/p>\n<h2><a id=\"five\"><\/a>5. The Reaction Energy Diagram For Acid-Catalyzed Hydration<\/h2>\n<p><strong>Reaction energy diagrams<\/strong> are helpful for visualizing changes in energy as reactants are transformed into products. Changes in energy (\u0394 E) are graphed on the y-axis, while reaction progress from reactants to products is graphed on the x-axis.<\/p>\n<p>In a reaction energy diagram, the local\u00a0<strong>maxima <\/strong><span style=\"color: #993366;\"><em>(&#8220;peaks&#8221;)<\/em><\/span> represent\u00a0<strong>transition states<\/strong> which include partial bonds and partial charges and exceptionally brief lifetimes.<\/p>\n<p>Local <strong>minima <\/strong><span style=\"color: #993366;\"><em>(&#8220;valleys&#8221;)\u00a0<\/em><span style=\"color: #000000;\">represent\u00a0<strong>intermediates<\/strong> with full charges and bonds, and can (at least potentially) be observed in solution.\u00a0<\/span><\/span><\/p>\n<p>The <strong>rate-determining step\u00a0<\/strong>is the step with the greatest difference in energy (\u0394 E) between reactants and the transition state.<\/p>\n<p>In hydration, the rate-determining step corresponds to the <strong>first\u00a0<\/strong>step &#8211; the protonation of the alkene with strong acid, which then results in the carbocation intermediate. In the second step (transition state #2) water adds to the carbocation, giving the protonated alcohol (oxonium ion) intermediate. This is followed by a third step (transition state #3) &#8211;\u00a0 deprotonation to give the neutral alcohol.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-35517\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/09\/10-reaction-energy-diagram-for-the-hydration-of-alkenes-with-acid-catalyst-formation-of-alcohols-transition-states.gif\" alt=\"reaction energy diagram for the hydration of alkenes with acid catalyst formation of alcohols transition states\" width=\"640\" height=\"419\" \/><\/a><\/p>\n<p>Although not shown in the diagram above,\u00a0 protonation of the alkene to give the <strong>less<\/strong> substituted carbocation would proceed through a significantly higher-energy transition state and also result in a significantly higher-energy carbocation intermediate.<\/p>\n<h2><a id=\"six\"><\/a>6. Carbocation Rearrangements<\/h2>\n<p>Hydration of alkenes can be accompanied by <strong>rearrangements<\/strong> if a hydride or alkyl shift results in a more stable carbocation. <span style=\"color: #800080;\"><em>(See, for example &#8211; <span style=\"color: #800080;\"><a style=\"color: #800080;\" href=\"https:\/\/www.masterorganicchemistry.com\/2012\/08\/15\/rearrangement-reactions-1-hydride-shifts\/\">Rearrangement Reactions &#8211; Hydride Shifts<\/a><\/span>)<\/em><\/span><\/p>\n<p>For example, hydration of the alkene below results in a considerable amount of a <strong>tertiary alcohol<\/strong> instead of the expected secondary alcohol product that would result from a simple Markovnikov addition.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-35518\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/09\/11-scheme-for-formation-of-alcohols-from-alkenes-and-acid-with-rearrangement.gif\" alt=\"reaction energy diagram for the hydration of alkenes with acid catalyst formation of alcohols transition states\" width=\"640\" height=\"272\" \/><\/a><\/p>\n<p>Why is that? See if you can draw the mechanism of the reaction that leads to this product:<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35508\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35508\"] {\n--wq-question-width: 100%;\n--wq-question-color: #009cff;\n--wq-question-height: auto;\n--wq-font-color: #444;\n}\n\n\t\t\t.wq-quiz-wrapper[data-id=\"35508\"] {\n\t\t\t\t--wq-question-width: 600px;\n\t\t\t}\n\n\t\t\t@media screen and (max-width: 600px) {\n\t\t\t\t.wq-quiz-wrapper[data-id=\"35508\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35508\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35508 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35508\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-fw7sq\" data-id=\"fw7sq\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2578-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2578-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper -->\n<p>In this case, a more stable tertiary carbocation is generated after migration of the CH<sub>3<\/sub> group on the adjacent carbon.<\/p>\n<p>Note that if one wants to <strong>avoid<\/strong> carbocation rearrangements in the formation of alcohols with Markovnikov selectivity, a good strategy is to use oxymercuration-demercuration instead.<em> (<span style=\"color: #800080;\">See article: <a style=\"color: #800080;\" href=\"https:\/\/www.masterorganicchemistry.com\/2023\/08\/31\/oxymercuration-demercuration\/\">Oxymercuration Demercuration of Alkenes<\/a><\/span>)\u00a0<\/em><\/p>\n<p><span style=\"color: #800080;\"><em>For more examples of rearrangement quizzes, see the &#8220;Quiz Yourself&#8221; section below.\u00a0<\/em><\/span><\/p>\n<h2><a id=\"seven\"><\/a>7. Addition of Alcohols To Alkenes With Acid<\/h2>\n<p>If an <strong>alcohol <\/strong>is used in place of <strong>water<\/strong>, subsequent treatment of alkenes with an acid catalyst can result in <strong>ethers<\/strong>.<\/p>\n<p>The reaction is essentially the same as that for the reaction with H<sub>2<\/sub>O. Protonation results in the most stable carbocation, which is then attacked by the alcohol. Deprotonation then gives the ether.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-35519\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/09\/13-when-acid-like-H2SO4-is-added-to-alkenes-in-the-presence-of-alcohols-ethers-can-form.gif\" alt=\"when acid like H2SO4 is added to alkenes in the presence of alcohols ethers can form\" width=\"640\" height=\"228\" \/><\/a><\/p>\n<p>See if you can draw the product in the reaction below:<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35509\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35509\"] {\n--wq-question-width: 100%;\n--wq-question-color: #009cff;\n--wq-question-height: auto;\n--wq-font-color: #444;\n}\n\n\t\t\t.wq-quiz-wrapper[data-id=\"35509\"] {\n\t\t\t\t--wq-question-width: 600px;\n\t\t\t}\n\n\t\t\t@media screen and (max-width: 600px) {\n\t\t\t\t.wq-quiz-wrapper[data-id=\"35509\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35509\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35509 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35509\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-8ywfr\" data-id=\"8ywfr\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2579-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2579-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper -->\n<p>This reaction can come in handy for making ethers that are otherwise difficult to make through, say, an S<sub>N<\/sub>2 reaction between an alkoxide and an alkyl halide. [<a href=\"#notetwo\">Note 2<\/a>]<\/p>\n<p><span style=\"color: #993366;\"><em>Much later, in the chapter on reactions of aromatic compounds, we&#8217;ll see examples of using t-butyl ethers as temporary protecting groups for aromatic alcohols &#8211; see this article on<span style=\"color: #993366;\"> <a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2018\/11\/26\/sulfonyl-blocking-groups-aromatic-synthesis\/\">Blocking Groups<\/a>.\u00a0<\/span><\/em><\/span><\/p>\n<h2><a id=\"eight\"><\/a>8.\u00a0 Intramolecular Reactions of Alcohols and Alkenes<\/h2>\n<p>If an alcohol and an alkene are present on the same molecule, then treatment with acid can result in the\u00a0<strong>intramolecular\u00a0<\/strong>formation of an ether, resulting in a new ring.<\/p>\n<p>It works best for the formation of 5- and 6-membered rings, as these rings are formed\u00a0<strong>fastest<\/strong> and also have the least\u00a0<strong>ring strain<\/strong>.<\/p>\n<p>See if you can draw the mechanism of this reaction:<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35510\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35510\"] {\n--wq-question-width: 100%;\n--wq-question-color: #009cff;\n--wq-question-height: auto;\n--wq-font-color: #444;\n}\n\n\t\t\t.wq-quiz-wrapper[data-id=\"35510\"] {\n\t\t\t\t--wq-question-width: 600px;\n\t\t\t}\n\n\t\t\t@media screen and (max-width: 600px) {\n\t\t\t\t.wq-quiz-wrapper[data-id=\"35510\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35510\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35510 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35510\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-hqf3m\" data-id=\"hqf3m\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2580-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2580-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper -->\n<p>Watch out for these kinds of examples, as they are commonly found on exams!<\/p>\n<h2><a id=\"nine\"><\/a>9. Summary<\/h2>\n<p>Hydration of alkenes and the addition of alcohols to alkenes are two examples of reactions that pass through what I sometimes call the &#8220;carbocation pathway&#8221; of alkene addition reactions.These reactions, along with addition of H-X to alkenes, all have the following in common.<\/p>\n<ul>\n<li>They pass through an intermediate\u00a0<strong>carbocation<\/strong> and are selective for\u00a0<strong>Markovnikov\u00a0<\/strong>products<\/li>\n<li>They give a\u00a0<strong>mixture\u00a0<\/strong>of\u00a0<em>syn<\/em> and\u00a0<em>anti<\/em>&#8211; addition products (i.e. are not stereoselective)<\/li>\n<li>Carbocation\u00a0<strong>rearrangements<\/strong> may occur.<\/li>\n<\/ul>\n<p>For more, (<span style=\"color: #993366;\"><em>See article &#8211; Alkene Addition Pattern #1 &#8211; <a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2013\/02\/22\/addition-pattern-1-the-carbocation-pathway\/\">The Carbocation Pathway<\/a><\/em>)<\/span><\/p>\n<hr \/>\n<h2><strong><a id=\"notes\"><\/a>Notes<\/strong><\/h2>\n<div class=\"related-articles\"><p><strong>Related Articles<\/strong><\/p><ul><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/02\/08\/markovnikovs-rule-1\/\" class=\"\"><span>Markovnikov Addition Of HCl To Alkenes<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2023\/08\/31\/oxymercuration-demercuration\/\" class=\"\"><span>Oxymercuration Demercuration of Alkenes<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/02\/26\/rearrangements-in-alkene-addition-reactions\/\" class=\"\"><span>Rearrangements in Alkene Addition Reactions<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/03\/28\/hydroboration-of-alkenes-the-mechanism\/\" class=\"\"><span>Hydroboration Oxidation of Alkenes<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/02\/22\/addition-pattern-1-the-carbocation-pathway\/\" class=\"\"><span>Addition Pattern #1: The \u201cCarbocation Pathway\u201d<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/08\/15\/rearrangement-reactions-1-hydride-shifts\/\" class=\"\"><span>Rearrangement Reactions (1) \u2013 Hydride Shifts<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/03\/15\/alkene-bromination-mechanism\/\" class=\"\"><span>Halogenation of Alkenes and Halohydrin Formation<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/10\/24\/the-williamson-ether-synthesis\/\" class=\"\"><span>The Williamson Ether Synthesis<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2018\/11\/26\/sulfonyl-blocking-groups-aromatic-synthesis\/\" class=\"\"><span>Aromatic Synthesis (3) \u2013 Sulfonyl Blocking Groups<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/05\/23\/whats-a-racemic-mixture\/\" class=\"\"><span>What\u2019s a Racemic Mixture?<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/01\/22\/alkene-addition-regioselectivity-syn-anti\/\" class=\"\"><span>Alkene Addition Reactions: \u201cRegioselectivity\u201d and \u201cStereoselectivity\u201d (Syn\/Anti)<\/span><\/a><\/li><\/ul><\/div>\n<p><strong><a id=\"noteone\"><\/a>Note 1.\u00a0<\/strong>Even if HSO<sub>4<\/sub>(-) does add to the carbocation to give an alkyl sulfate, these are quite readily hydrolyzed in water to give alcohols.<\/p>\n<p><strong><a id=\"notetwo\"><\/a>Note 2<\/strong>. Although it should be noted that adding acid to alcohols also invites the possibility of elimination reactions to give alkenes! For our purposes, something like oxymercuration is probably a better choice for making ethers from alkenes, since it is not accompanied by elimination.<\/p>\n<hr \/>\n<h2><strong><a id=\"quiz\"><\/a>Quiz Yourself!<\/strong><\/h2>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/3586-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/3602-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/3587-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/2581-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <br \/>\n<\/p>\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/2582-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <br \/>\n<\/p>\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/2583-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <br \/>\n<\/p>\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/2584-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <br \/>\n<\/p>\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/2585-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <br \/>\n<\/p>\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/2586-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <br \/>\n<\/p>\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/2587-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n<hr \/>\n<h2><strong><a id=\"references\"><\/a>(Advanced) References and Further Reading<\/strong><\/h2>\n<ol>\n<li><strong>The Electrolyte Effects in the Hydration of Isobutene<\/strong><br \/>\nFrank G. Ciapetta and Martin Kilpatrick<strong><br \/>\n<\/strong><em>Journal of the American Chemical Society<\/em><strong> 1948, <\/strong><em>70<\/em> (2), 639-646<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja01182a062\">10.1021\/ja01182a062<\/a><br \/>\nAn early paper on the acid-catalyzed hydration of alkenes.<\/li>\n<li><strong>The Dependence of the Rate of Hydration of Isobutene on the Acidity Function, <em>H<sub>0<\/sub><\/em>, and the Mechanism for Olefin Hydration in Aqueous Acids<br \/>\n<\/strong>Robert W. Taft Jr.<strong><br \/>\n<\/strong><em>Journal of the American Chemical Society<\/em> <strong>1952,<\/strong> <em>74<\/em> (21), 5372-5376<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja01141a046\">10.1021\/ja01141a046<\/a><br \/>\nThis early paper demonstrates that the rate of olefin hydration increases with the acidity of the medium, providing evidence that a carbocation is the intermediate in the reaction \u2013 these become increasingly stable as the acidity of the medium increases.<\/li>\n<li><strong><a id=\"refthree\"><\/a>The Steric Course of Hydration of 1,2-Dimethylcyclohexene<\/strong><br \/>\nCAROL H. COLLINS and GEORGE S. HAMMOND<br \/>\n<em>The Journal of Organic Chemistry<\/em> <strong>1960<\/strong> 25 (6), 911-913<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/jo01076a009\">10.1021\/jo01076a009<\/a><br \/>\nIn this study, 1,2-dimethylcyclohexene was treated with 0.1 M nitric acid for 1 day at 50\u00b0C and a 52:48 ratio of\u00a0<em>trans<\/em> to\u00a0<em>cis<\/em> alcohols was obtained, showing the reaction is not stereoselective.<\/li>\n<li><strong>General acid catalysis in the hydration of simple olefins. Mechanism of olefin hydration<br \/>\n<\/strong>A. J. Kresge, Y. Chiang, P. H. Fitzgerald, R. S. McDonald, and G. H. Schmid<strong><br \/>\n<\/strong><em>Journal of the American Chemical Society<\/em><strong> 1971, <\/strong><em>93<\/em> (19), 4907-4908<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00748a043\">10.1021\/ja00748a043<\/a><br \/>\nThe key finding of this paper is that 2,3-dimethyl-2-butene and trans-cyclooctene undergo hydration with general acid catalysis and therefore other alkenes do as well (i.e. direct protonation of the alkene with no intermediate pi complex).<\/li>\n<li><strong>Structural effects on the acid-catalyzed hydration of alkenes<br \/>\n<\/strong>Vincent J. Nowlan and Thomas T. Tidwell<br \/>\n<em>Accounts of Chemical Research<\/em><strong> 1977, <\/strong><em>10<\/em> (7), 252-258<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ar50115a004\">10.1021\/ar50115a004<\/a><br \/>\nThis is a useful account that reviews all the work done on investigating the acid-catalyzed hydration of alkenes up to that point. It also ties this topic to carbocation chemistry \u2013 the 2-norbornyl cation, which was a hot topic at the time, is mentioned towards the end.<\/li>\n<li><strong>Enthalpies of hydration of alkenes. 4. Formation of acyclic tert-alcohols<br \/>\n<\/strong>Kenneth B. Wiberg and Shide Hao<strong><br \/>\n<\/strong><em>The Journal of Organic Chemistry<\/em><strong> 1991, <\/strong><em>56<\/em> (17), 5108-5110<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/jo00017a022\">10.1021\/jo00017a022<\/a><br \/>\nA nice calorimetric study on the hydration of alkenes, determining the enthalpy of this reaction.<\/li>\n<li><strong><a id=\"refseven\"><\/a>PREPARATION OF tert-BUTYL ARYL ETHERS<\/strong><br \/>\nDONALD R. STEVENS<br \/>\n<em>The Journal of Organic Chemistry<\/em> <strong>1955<\/strong> 20 (9), 1232-1236<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/jo01126a010\">10.1021\/jo01126a010<\/a><br \/>\n&#8220;tert-alkyl aryl ethers can be prepared in fairly high yields by simply passing isobutylene into the phenol at relatively low temperatures and in the presence of only a trace of sulfuric acid as the catalyst.&#8221;<\/li>\n<\/ol>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Hydration of Alkenes to Give Alcohols When alkenes are treated with aqueous acid (H3O+) they can be converted to alcohols. Formation of the new C-OH <\/p>\n","protected":false},"author":1,"featured_media":35543,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1418],"tags":[403,294,167,169,397,850,898,887],"post_folder":[],"class_list":["post-35488","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-alkene-reactions","tag-acid","tag-addition","tag-alcohols","tag-alkenes","tag-carbocations","tag-ethers","tag-hydration","tag-markovnikov"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Hydration of Alkenes With Aqueous Acid &#8211; Master Organic Chemistry<\/title>\n<meta name=\"description\" content=\"Alkenes are converted to alcohols with when treated with aqueous acid (H3O+). The reaction goes through a carbocation and rearrangements can occur\" \/>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/www.masterorganicchemistry.com\/2023\/09\/15\/hydration-alkenes-acid\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Hydration of Alkenes With Aqueous Acid &#8211; Master Organic Chemistry\" \/>\n<meta property=\"og:description\" content=\"Alkenes are converted to alcohols with when treated with aqueous acid (H3O+). The reaction goes through a carbocation and rearrangements can occur\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.masterorganicchemistry.com\/2023\/09\/15\/hydration-alkenes-acid\/\" \/>\n<meta property=\"og:site_name\" content=\"Master Organic Chemistry\" \/>\n<meta property=\"article:publisher\" content=\"https:\/\/www.facebook.com\/Master-Organic-Chemistry-242610599108055\/\" \/>\n<meta property=\"article:published_time\" content=\"2023-09-15T20:00:04+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2025-12-12T09:41:55+00:00\" \/>\n<meta property=\"og:image\" content=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/09\/0-summary-of-Acid-catalyzed-hydration-of-alkenes-to-give-alcohols-and-addition-of-alcohols-to-give-ethers-2.gif\" \/>\n\t<meta property=\"og:image:width\" content=\"874\" \/>\n\t<meta property=\"og:image:height\" content=\"862\" \/>\n\t<meta property=\"og:image:type\" content=\"image\/gif\" \/>\n<meta name=\"author\" content=\"James Ashenhurst\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:label1\" content=\"Written by\" \/>\n\t<meta name=\"twitter:data1\" content=\"James Ashenhurst\" \/>\n\t<meta name=\"twitter:label2\" content=\"Est. reading time\" \/>\n\t<meta name=\"twitter:data2\" content=\"15 minutes\" \/>\n<script type=\"application\/ld+json\" class=\"yoast-schema-graph\">{\"@context\":\"https:\\\/\\\/schema.org\",\"@graph\":[{\"@type\":\"Article\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2023\\\/09\\\/15\\\/hydration-alkenes-acid\\\/#article\",\"isPartOf\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2023\\\/09\\\/15\\\/hydration-alkenes-acid\\\/\"},\"author\":{\"name\":\"James Ashenhurst\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#\\\/schema\\\/person\\\/78d83ec7d02b4b7365bade2cedaef80c\"},\"headline\":\"Hydration of Alkenes With Aqueous Acid\",\"datePublished\":\"2023-09-15T20:00:04+00:00\",\"dateModified\":\"2025-12-12T09:41:55+00:00\",\"mainEntityOfPage\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2023\\\/09\\\/15\\\/hydration-alkenes-acid\\\/\"},\"wordCount\":2579,\"commentCount\":7,\"publisher\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#organization\"},\"image\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2023\\\/09\\\/15\\\/hydration-alkenes-acid\\\/#primaryimage\"},\"thumbnailUrl\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/wp-content\\\/uploads\\\/2023\\\/09\\\/0-summary-of-Acid-catalyzed-hydration-of-alkenes-to-give-alcohols-and-addition-of-alcohols-to-give-ethers-2.gif\",\"keywords\":[\"acid\",\"addition\",\"alcohols\",\"alkenes\",\"carbocations\",\"ethers\",\"hydration\",\"markovnikov\"],\"articleSection\":[\"Alkene Reactions\"],\"inLanguage\":\"en-US\",\"potentialAction\":[{\"@type\":\"CommentAction\",\"name\":\"Comment\",\"target\":[\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2023\\\/09\\\/15\\\/hydration-alkenes-acid\\\/#respond\"]}]},{\"@type\":\"WebPage\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2023\\\/09\\\/15\\\/hydration-alkenes-acid\\\/\",\"url\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2023\\\/09\\\/15\\\/hydration-alkenes-acid\\\/\",\"name\":\"Hydration of Alkenes With Aqueous Acid &#8211; Master Organic Chemistry\",\"isPartOf\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#website\"},\"primaryImageOfPage\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2023\\\/09\\\/15\\\/hydration-alkenes-acid\\\/#primaryimage\"},\"image\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2023\\\/09\\\/15\\\/hydration-alkenes-acid\\\/#primaryimage\"},\"thumbnailUrl\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/wp-content\\\/uploads\\\/2023\\\/09\\\/0-summary-of-Acid-catalyzed-hydration-of-alkenes-to-give-alcohols-and-addition-of-alcohols-to-give-ethers-2.gif\",\"datePublished\":\"2023-09-15T20:00:04+00:00\",\"dateModified\":\"2025-12-12T09:41:55+00:00\",\"description\":\"Alkenes are converted to alcohols with when treated with aqueous acid (H3O+). The reaction goes through a carbocation and rearrangements can occur\",\"breadcrumb\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2023\\\/09\\\/15\\\/hydration-alkenes-acid\\\/#breadcrumb\"},\"inLanguage\":\"en-US\",\"potentialAction\":[{\"@type\":\"ReadAction\",\"target\":[\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2023\\\/09\\\/15\\\/hydration-alkenes-acid\\\/\"]}]},{\"@type\":\"ImageObject\",\"inLanguage\":\"en-US\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2023\\\/09\\\/15\\\/hydration-alkenes-acid\\\/#primaryimage\",\"url\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/wp-content\\\/uploads\\\/2023\\\/09\\\/0-summary-of-Acid-catalyzed-hydration-of-alkenes-to-give-alcohols-and-addition-of-alcohols-to-give-ethers-2.gif\",\"contentUrl\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/wp-content\\\/uploads\\\/2023\\\/09\\\/0-summary-of-Acid-catalyzed-hydration-of-alkenes-to-give-alcohols-and-addition-of-alcohols-to-give-ethers-2.gif\",\"width\":874,\"height\":862,\"caption\":\"summary of Acid catalyzed hydration of alkenes to give alcohols and addition of alcohols to give ethers\"},{\"@type\":\"BreadcrumbList\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2023\\\/09\\\/15\\\/hydration-alkenes-acid\\\/#breadcrumb\",\"itemListElement\":[{\"@type\":\"ListItem\",\"position\":1,\"name\":\"Home\",\"item\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/\"},{\"@type\":\"ListItem\",\"position\":2,\"name\":\"Hydration of Alkenes With Aqueous Acid\"}]},{\"@type\":\"WebSite\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#website\",\"url\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/\",\"name\":\"Master Organic Chemistry\",\"description\":\"\",\"publisher\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#organization\"},\"potentialAction\":[{\"@type\":\"SearchAction\",\"target\":{\"@type\":\"EntryPoint\",\"urlTemplate\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/?s={search_term_string}\"},\"query-input\":{\"@type\":\"PropertyValueSpecification\",\"valueRequired\":true,\"valueName\":\"search_term_string\"}}],\"inLanguage\":\"en-US\"},{\"@type\":\"Organization\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#organization\",\"name\":\"Master Organic Chemistry\",\"url\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/\",\"logo\":{\"@type\":\"ImageObject\",\"inLanguage\":\"en-US\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#\\\/schema\\\/logo\\\/image\\\/\",\"url\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/wp-content\\\/uploads\\\/2019\\\/04\\\/cutmypic.png\",\"contentUrl\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/wp-content\\\/uploads\\\/2019\\\/04\\\/cutmypic.png\",\"width\":225,\"height\":225,\"caption\":\"Master Organic Chemistry\"},\"image\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#\\\/schema\\\/logo\\\/image\\\/\"},\"sameAs\":[\"https:\\\/\\\/www.facebook.com\\\/Master-Organic-Chemistry-242610599108055\\\/\"]},{\"@type\":\"Person\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#\\\/schema\\\/person\\\/78d83ec7d02b4b7365bade2cedaef80c\",\"name\":\"James Ashenhurst\",\"image\":{\"@type\":\"ImageObject\",\"inLanguage\":\"en-US\",\"@id\":\"https:\\\/\\\/secure.gravatar.com\\\/avatar\\\/f9e9df435875e5e6b0bdff6b8522a7279d5717644b3efa7299da22c837bf9fcf?s=96&d=retro&r=g\",\"url\":\"https:\\\/\\\/secure.gravatar.com\\\/avatar\\\/f9e9df435875e5e6b0bdff6b8522a7279d5717644b3efa7299da22c837bf9fcf?s=96&d=retro&r=g\",\"contentUrl\":\"https:\\\/\\\/secure.gravatar.com\\\/avatar\\\/f9e9df435875e5e6b0bdff6b8522a7279d5717644b3efa7299da22c837bf9fcf?s=96&d=retro&r=g\",\"caption\":\"James Ashenhurst\"},\"description\":\"Ph.D. 2006, McGill University (James L. Gleason). Postdoctoral Associate, 2008-2010, Massachusetts Institute of Technology (M. Movassaghi). Founder, Master Organic Chemistry, 2010-present.\",\"sameAs\":[\"https:\\\/\\\/www.masterorganicchemistry.com\\\/about\\\/\"],\"url\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/author\\\/james\\\/\"}]}<\/script>\n<!-- \/ Yoast SEO plugin. -->","yoast_head_json":{"title":"Hydration of Alkenes With Aqueous Acid &#8211; Master Organic Chemistry","description":"Alkenes are converted to alcohols with when treated with aqueous acid (H3O+). The reaction goes through a carbocation and rearrangements can occur","robots":{"index":"index","follow":"follow","max-snippet":"max-snippet:-1","max-image-preview":"max-image-preview:large","max-video-preview":"max-video-preview:-1"},"canonical":"https:\/\/www.masterorganicchemistry.com\/2023\/09\/15\/hydration-alkenes-acid\/","og_locale":"en_US","og_type":"article","og_title":"Hydration of Alkenes With Aqueous Acid &#8211; Master Organic Chemistry","og_description":"Alkenes are converted to alcohols with when treated with aqueous acid (H3O+). The reaction goes through a carbocation and rearrangements can occur","og_url":"https:\/\/www.masterorganicchemistry.com\/2023\/09\/15\/hydration-alkenes-acid\/","og_site_name":"Master Organic Chemistry","article_publisher":"https:\/\/www.facebook.com\/Master-Organic-Chemistry-242610599108055\/","article_published_time":"2023-09-15T20:00:04+00:00","article_modified_time":"2025-12-12T09:41:55+00:00","og_image":[{"width":874,"height":862,"url":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/09\/0-summary-of-Acid-catalyzed-hydration-of-alkenes-to-give-alcohols-and-addition-of-alcohols-to-give-ethers-2.gif","type":"image\/gif"}],"author":"James Ashenhurst","twitter_card":"summary_large_image","twitter_misc":{"Written by":"James Ashenhurst","Est. reading time":"15 minutes"},"schema":{"@context":"https:\/\/schema.org","@graph":[{"@type":"Article","@id":"https:\/\/www.masterorganicchemistry.com\/2023\/09\/15\/hydration-alkenes-acid\/#article","isPartOf":{"@id":"https:\/\/www.masterorganicchemistry.com\/2023\/09\/15\/hydration-alkenes-acid\/"},"author":{"name":"James Ashenhurst","@id":"https:\/\/www.masterorganicchemistry.com\/#\/schema\/person\/78d83ec7d02b4b7365bade2cedaef80c"},"headline":"Hydration of Alkenes With Aqueous Acid","datePublished":"2023-09-15T20:00:04+00:00","dateModified":"2025-12-12T09:41:55+00:00","mainEntityOfPage":{"@id":"https:\/\/www.masterorganicchemistry.com\/2023\/09\/15\/hydration-alkenes-acid\/"},"wordCount":2579,"commentCount":7,"publisher":{"@id":"https:\/\/www.masterorganicchemistry.com\/#organization"},"image":{"@id":"https:\/\/www.masterorganicchemistry.com\/2023\/09\/15\/hydration-alkenes-acid\/#primaryimage"},"thumbnailUrl":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/09\/0-summary-of-Acid-catalyzed-hydration-of-alkenes-to-give-alcohols-and-addition-of-alcohols-to-give-ethers-2.gif","keywords":["acid","addition","alcohols","alkenes","carbocations","ethers","hydration","markovnikov"],"articleSection":["Alkene Reactions"],"inLanguage":"en-US","potentialAction":[{"@type":"CommentAction","name":"Comment","target":["https:\/\/www.masterorganicchemistry.com\/2023\/09\/15\/hydration-alkenes-acid\/#respond"]}]},{"@type":"WebPage","@id":"https:\/\/www.masterorganicchemistry.com\/2023\/09\/15\/hydration-alkenes-acid\/","url":"https:\/\/www.masterorganicchemistry.com\/2023\/09\/15\/hydration-alkenes-acid\/","name":"Hydration of Alkenes With Aqueous Acid &#8211; Master Organic Chemistry","isPartOf":{"@id":"https:\/\/www.masterorganicchemistry.com\/#website"},"primaryImageOfPage":{"@id":"https:\/\/www.masterorganicchemistry.com\/2023\/09\/15\/hydration-alkenes-acid\/#primaryimage"},"image":{"@id":"https:\/\/www.masterorganicchemistry.com\/2023\/09\/15\/hydration-alkenes-acid\/#primaryimage"},"thumbnailUrl":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/09\/0-summary-of-Acid-catalyzed-hydration-of-alkenes-to-give-alcohols-and-addition-of-alcohols-to-give-ethers-2.gif","datePublished":"2023-09-15T20:00:04+00:00","dateModified":"2025-12-12T09:41:55+00:00","description":"Alkenes are converted to alcohols with when treated with aqueous acid (H3O+). The reaction goes through a carbocation and rearrangements can occur","breadcrumb":{"@id":"https:\/\/www.masterorganicchemistry.com\/2023\/09\/15\/hydration-alkenes-acid\/#breadcrumb"},"inLanguage":"en-US","potentialAction":[{"@type":"ReadAction","target":["https:\/\/www.masterorganicchemistry.com\/2023\/09\/15\/hydration-alkenes-acid\/"]}]},{"@type":"ImageObject","inLanguage":"en-US","@id":"https:\/\/www.masterorganicchemistry.com\/2023\/09\/15\/hydration-alkenes-acid\/#primaryimage","url":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/09\/0-summary-of-Acid-catalyzed-hydration-of-alkenes-to-give-alcohols-and-addition-of-alcohols-to-give-ethers-2.gif","contentUrl":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/09\/0-summary-of-Acid-catalyzed-hydration-of-alkenes-to-give-alcohols-and-addition-of-alcohols-to-give-ethers-2.gif","width":874,"height":862,"caption":"summary of Acid catalyzed hydration of alkenes to give alcohols and addition of alcohols to give ethers"},{"@type":"BreadcrumbList","@id":"https:\/\/www.masterorganicchemistry.com\/2023\/09\/15\/hydration-alkenes-acid\/#breadcrumb","itemListElement":[{"@type":"ListItem","position":1,"name":"Home","item":"https:\/\/www.masterorganicchemistry.com\/"},{"@type":"ListItem","position":2,"name":"Hydration of Alkenes With Aqueous Acid"}]},{"@type":"WebSite","@id":"https:\/\/www.masterorganicchemistry.com\/#website","url":"https:\/\/www.masterorganicchemistry.com\/","name":"Master Organic Chemistry","description":"","publisher":{"@id":"https:\/\/www.masterorganicchemistry.com\/#organization"},"potentialAction":[{"@type":"SearchAction","target":{"@type":"EntryPoint","urlTemplate":"https:\/\/www.masterorganicchemistry.com\/?s={search_term_string}"},"query-input":{"@type":"PropertyValueSpecification","valueRequired":true,"valueName":"search_term_string"}}],"inLanguage":"en-US"},{"@type":"Organization","@id":"https:\/\/www.masterorganicchemistry.com\/#organization","name":"Master Organic Chemistry","url":"https:\/\/www.masterorganicchemistry.com\/","logo":{"@type":"ImageObject","inLanguage":"en-US","@id":"https:\/\/www.masterorganicchemistry.com\/#\/schema\/logo\/image\/","url":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/04\/cutmypic.png","contentUrl":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/04\/cutmypic.png","width":225,"height":225,"caption":"Master Organic Chemistry"},"image":{"@id":"https:\/\/www.masterorganicchemistry.com\/#\/schema\/logo\/image\/"},"sameAs":["https:\/\/www.facebook.com\/Master-Organic-Chemistry-242610599108055\/"]},{"@type":"Person","@id":"https:\/\/www.masterorganicchemistry.com\/#\/schema\/person\/78d83ec7d02b4b7365bade2cedaef80c","name":"James Ashenhurst","image":{"@type":"ImageObject","inLanguage":"en-US","@id":"https:\/\/secure.gravatar.com\/avatar\/f9e9df435875e5e6b0bdff6b8522a7279d5717644b3efa7299da22c837bf9fcf?s=96&d=retro&r=g","url":"https:\/\/secure.gravatar.com\/avatar\/f9e9df435875e5e6b0bdff6b8522a7279d5717644b3efa7299da22c837bf9fcf?s=96&d=retro&r=g","contentUrl":"https:\/\/secure.gravatar.com\/avatar\/f9e9df435875e5e6b0bdff6b8522a7279d5717644b3efa7299da22c837bf9fcf?s=96&d=retro&r=g","caption":"James Ashenhurst"},"description":"Ph.D. 2006, McGill University (James L. Gleason). Postdoctoral Associate, 2008-2010, Massachusetts Institute of Technology (M. Movassaghi). Founder, Master Organic Chemistry, 2010-present.","sameAs":["https:\/\/www.masterorganicchemistry.com\/about\/"],"url":"https:\/\/www.masterorganicchemistry.com\/author\/james\/"}]}},"_links":{"self":[{"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/posts\/35488","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/comments?post=35488"}],"version-history":[{"count":0,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/posts\/35488\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/media\/35543"}],"wp:attachment":[{"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/media?parent=35488"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/categories?post=35488"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/tags?post=35488"},{"taxonomy":"post_folder","embeddable":true,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/post_folder?post=35488"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}