{"id":8806,"date":"2015-03-10T18:24:23","date_gmt":"2015-03-10T23:24:23","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=8806"},"modified":"2026-05-03T04:41:28","modified_gmt":"2026-05-03T09:41:28","slug":"tosylates-and-mesylates","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2015\/03\/10\/tosylates-and-mesylates\/","title":{"rendered":"Tosylates And Mesylates"},"content":{"rendered":"<p><strong>All About Tosylates and Mesylates<\/strong><\/p>\n<ul>\n<li>By themselves, alcohols are poor leaving groups since the hydroxide ion (HO-) is a strong base<\/li>\n<li>The OH group can be converted into a much better leaving group through conversion to a\u00a0<strong>sulfonate<\/strong> group such as\u00a0<em>p-<\/em>toluenesulfonyl (&#8220;tosyl&#8221;, abbreviated Ts) or methanesulfonyl (&#8220;mesyl&#8221;, abbreviated Ms)<\/li>\n<li>Installing these groups does\u00a0<strong>not<\/strong> affect the stereochemistry of the alcohol<\/li>\n<li>The OTs and OMs groups can participate in substitution and elimination reactions.<\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-15196\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/0-summary-conversion-of-alcohols-to-good-leaving-groups-tosylates-sulfonates-mesylates-occurs-with-no-change-or-inversion-in-stereochemistry-easy-way-to-make-oh-into-good-leaving-group.gif\" alt=\"summary conversion of alcohols to good leaving groups tosylates sulfonates mesylates occurs with no change or inversion in stereochemistry easy way to make oh into good leaving group\" width=\"600\" height=\"413\" \/><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">Making Alcohols Into Good Leaving Groups (Part 2)<\/a><\/li>\n<li><a href=\"#two\">A Good Idea That Doesn&#8217;t Actually Work Well: Sulfate Leaving Groups<\/a><\/li>\n<li><a href=\"#three\">Introducing &#8220;Tosylates&#8221; and &#8220;Mesylates&#8221;<\/a><\/li>\n<li><a href=\"#four\">How Tosylates And Mesylates Are Made From Alcohols<\/a><\/li>\n<li><a href=\"#five\">Four Specific Examples of Tosylates and Mesylates In Action<\/a><\/li>\n<li><a href=\"#six\">Summary: Tosylates and Mesylates<\/a><\/li>\n<li><a href=\"#notes\">Notes<\/a><\/li>\n<li><a href=\"#quizzes\">Quiz Yourself!<\/a><\/li>\n<li><a href=\"#references\">(Advanced) References and Further Reading<\/a><\/li>\n<\/ol>\n<hr \/>\n<h2><strong><a id=\"one\"><\/a>1. Making Alcohols Into Good Leaving Groups, Part 2<\/strong><\/h2>\n<p>We&#8217;ve seen that<strong> alcohols are poor substrates for substitution reactions<\/strong>. The main problem is that the hydroxyl group is a strong base, and thus a <a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/04\/12\/what-makes-a-good-leaving-group\/\">poor leaving group<\/a>.<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-15197\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-by-themselves-alcohols-are-poor-leaving-groups-since-they-are-strong-bases-will-not-react-with-cyanide-for-example.gif\" alt=\"by themselves alcohols are poor leaving groups since they are strong bases will not react with cyanide for example\" width=\"600\" height=\"119\" \/><\/p>\n<p>In the<a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/02\/27\/making-alkyl-halides-from-alcohols\/\"> last post<\/a> we saw that we can convert alcohols into alkyl halides by adding strong \u00a0hydrohalic acids (HCl, HBr, HI): \u00a0the strong acid protonates R-OH to give R-OH<sub>2<\/sub><sup>+<\/sup> (with the better leaving group, H<sub>2<\/sub>O) and then substitution by the halide ion can occur.<\/p>\n<p>In contrast to alcohols, alkyl halides are GREAT substrates for nucleophilic substitution reactions.<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-15198\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-substitution-reactions-of-alcohols-can-work-well-if-strong-acid-is-used-eg-hbr-leads-to-alkyl-bromide-trouble-is-it-that-it-is-harsh.gif\" alt=\"substitution reactions of alcohols can work well if strong acid is used eg hbr leads to alkyl bromide trouble is it that it is harsh\" width=\"600\" height=\"217\" \/><\/p>\n<p>Unfortunately this doesn&#8217;t <em>always<\/em> work well. There are two main problems. First of all, on certain secondary alcohols the reaction proceeds through an S<sub>N<\/sub>1 pathway, which can lead to rearrangements. Secondly, in so doing, we can end up scrambling any stereocenters that are present. For instance if we start with one enantiomer in the reaction below, we end up with some racemization of the final product.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15199\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-converting-alcohols-to-alkyl-halides-with-strong-acid-can-lead-to-rearrangement-reactions-such-as-hydride-shift-alkyl-shift.gif\" alt=\"converting alcohols to alkyl halides with strong acid can lead to rearrangement reactions such as hydride shift alkyl shift\" width=\"600\" height=\"222\" \/><\/p>\n<p>So is there some other way to convert alcohols into good leaving groups that doesn&#8217;t have these problems?<\/p>\n<p>Sure thing!<\/p>\n<h2><a id=\"two\"><\/a>2. One Good Idea (Which Doesn&#8217;t Actually Work That Well)<\/h2>\n<p>We all know that hydroxide (HO- ) is a strong base. But have we seen any examples of <strong>weak bases with a negative charge on the oxygen?<\/strong><\/p>\n<p>Yes! Sulfuric acid (H<sub>2<\/sub>SO<sub>4<\/sub>) is a very strong acid (pK<sub>a<\/sub> of about -3) and its conjugate base, HSO<sub>3<\/sub>O<sup>\u2013<\/sup> , is therefore a weak base. This is due to two key factors &#8211; first of all, <strong>delocalization<\/strong> of charge on the other oxygens through resonance, and secondly, the<strong> inductive effect<\/strong> of those oxygens helping to redistribute the charge.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-33291\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2015\/03\/4-converting-alcohols-into-better-leaving-group-need-way-of-stabilizing-negative-charge-oh-to-something-weaker-and-resonance-stabilized-like-sulfate.gif\" alt=\"converting alcohols into better leaving group need way of stabilizing negative charge oh to something weaker and resonance stabilized like sulfate\" width=\"641\" height=\"248\" \/><\/a><\/p>\n<p>So in a perfect world, if we had some way of easily turning an alcohol (R-OH) into an alkyl hydrogen sulfate (R-OSO<sub>3<\/sub>H) then we&#8217;d have a nice way of making an alcohol into a good leaving group.<\/p>\n<p>So how might this work in practice? Actually it doesn&#8217;t work very well!<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-33293\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2015\/03\/5-problem-with-sulfate-as-leaving-group-is-that-it-is-acidic-and-might-protonate-nucleophile-also-polar-and-difficult-to-purify.gif\" alt=\"problem with sulfate as leaving group is that it is acidic and might protonate nucleophile also polar and difficult to purify\" width=\"640\" height=\"262\" \/><\/a><\/p>\n<p>It&#8217;s not that <sup>\u2013<\/sup>OSO<sub>3<\/sub>H is a poor leaving group (it&#8217;s a great leaving group). The problem is that <strong>many nucleophiles are quite basic<\/strong> (remember &#8211; <strong><a href=\"https:\/\/www.masterorganicchemistry.com\/2010\/04\/19\/the-conjugate-base-is-always-a-stronger-nucleophile\/\">the conjugate base is a better nucleophile<\/a><\/strong>) and the OSO<sub>3<\/sub>H still has a very acidic proton (that OH group has a pK<sub>a<\/sub> of about 2, making it a stronger acid than acetic acid).<\/p>\n<p>The bottom line is that if we add a basic nucleophile, <strong>an acid base reaction will occur<\/strong> instead of our desired substitution reaction. The nucleophile will be protonated into its conjugate acid (less nucleophilic) and any substitution reactions will be considerably slower. Not ideal!<\/p>\n<h2><a id=\"three\"><\/a>3. Introducing &#8220;Tosylates&#8221; and &#8220;Mesylates&#8221;<\/h2>\n<p>Is there some way around this? Sure! It&#8217;s just a matter of replacing that OH group on the sulfur by some kind of relatively inert organic group (R group) that doesn&#8217;t have an acidic proton.<\/p>\n<p>If we swap in a methyl group (CH<sub>3<\/sub>) our leaving group would be <sup>\u2013<\/sup>OSO<span style=\"font-size: small;\"><span style=\"line-height: 20px;\">2<\/span><\/span>CH<sub>3<\/sub>, or &#8220;methanesulfonate&#8221; (commonly called, &#8220;<strong>mesylate<\/strong><strong>&#8221; <\/strong>and abbreviated\u00a0<strong>OMs.\u00a0<\/strong>This has all the advantages of a great leaving group without the drawback of an acidic proton to react with nucleophiles.<\/p>\n<p>Another popular option is using the conjugate base of\u00a0<em>p<\/em>-toluenesulfonic acid, (&#8220;p-toluenesulfonate&#8221;) commonly called\u00a0<strong>&#8220;tosylate&#8221;\u00a0<\/strong>and abbreviated <b>OTs<\/b>.<\/p>\n<p>These groups have essentially identical leaving group ability and for our purposes are interchangeable. Some textbooks tend to use Ts more, others use Ms. It doesn&#8217;t really matter for us at this stage: they both work.<\/p>\n<p>[<span style=\"color: #993366;\"><em>A third option, less commonly seen in introductory courses, is the &#8220;triflate&#8221; (Tf) group, which replaces the three hydrogens on methanesulfonate with three fluorines. The conjugate acid, trifluoromethanesulfonic acid, is among the more acidic species known (pK<sub>a<\/sub> of -13!) and for this reason, triflate is a really &#8220;hot&#8221; leaving group when attached to alkyl groups: it likes to leave of its own accord! It&#8217;s more commonly used on aromatic alcohols and other species that don&#8217;t form carbocations as easily]<\/em><\/span><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-33292\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2015\/03\/6-advantage-of-tosylate-paratoluenesulfonate-and-mesylate-methanesulfonate-is-they-are-organic-molecules-good-leaving-groups-stabilized-negative-charge-structure-ots-oms.gif\" alt=\"advantage of tosylate paratoluenesulfonate and mesylate methanesulfonate is they are organic molecules good leaving groups stabilized negative charge structure ots oms\" width=\"640\" height=\"504\" \/><\/a><\/p>\n<h2><b><a id=\"four\"><\/a>4. How Do We Make Mesylates And Tosylates From Alcohols?\u00a0<\/b><\/h2>\n<p>So how can we apply this? If we have an alcohol, how do we turn that hydroxyl into a tosyl or mesyl group?<\/p>\n<p>It&#8217;s relatively straightforward actually. We use &#8220;mesyl chloride&#8221; (MsCl) or &#8220;tosyl chloride&#8221; (TsCl), and the neutral alcohol performs a substitution reaction <b>on sulfur<\/b>, leading to formation of O-S and breakage of S-Cl. Then, deprotonation of the charged alcohol leads to the neutral mesylate or tosylate.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"wp-image-45785\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2015\/03\/6a-tscl-and-mscl-toluenesulfonyl-chloride-and-mesyl-chloride-convert-alcohols-to-good-leaving-groups.gif\" alt=\"\" width=\"500\" height=\"198\" \/><\/a><\/p>\n<p>Note that the\u00a0<strong>stereochemistry is completely unchanged here<\/strong> (<span style=\"text-decoration: underline;\">unlike<\/span> if we had used H-Cl, for example). Watch out for this &#8211; stereochemistry is often tested on exams!<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15203\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/7-how-to-convert-alcohol-into-mesylate-or-tosylate-use-mesyl-chloride-or-tosyl-chloride-with-base-like-pyridine-does-not-change-alcohol-stereochemistry.gif\" alt=\"how to convert alcohol into mesylate or tosylate use mesyl chloride or tosyl chloride with base like pyridine does not change alcohol stereochemistry\" width=\"630\" height=\"438\" \/><\/p>\n<p><span style=\"color: #993366;\"><em>[By the way &#8211; sometimes you might see that an organic base such as <strong>pyridine\u00a0<\/strong>is also added, which helps the process along by removing HCl as it is formed. ]<\/em><\/span><\/p>\n<h2><a id=\"five\"><\/a>5. Four Specific Examples Of Tosylates and Mesylates In Action<\/h2>\n<p>Let&#8217;s finish up by seeing some specific examples of Ts\u00a0and Ms in action. As they contain a good leaving group, alkyl tosylates or mesylates can perform all of the substitution and elimination reactions of alkyl halides. A few examples are shown below. \u00a0Get familiar with MsCl and TsCl in both their abbreviated and expanded (i.e. &#8220;drawn-out&#8221;) forms.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15204\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/8-tosylates-and-mesylates-examples-converting-alcohols-to-mesylates-reaction-sn2-cyanide-acetylide-alcohol-to-tosylate-thiol.gif\" alt=\"tosylates and mesylates examples converting alcohols to mesylates reaction sn2 cyanide acetylide alcohol to tosylate thiol\" width=\"630\" height=\"485\" \/><\/p>\n<h2><a id=\"six\"><\/a>6. Summary: Tosylates And Mesylates<\/h2>\n<p>In the last two posts we&#8217;ve seen how useful it is to be able to convert alcohols to good leaving groups. In our next post we&#8217;ll cover one last method to do this that involves some new reagents, PBr<sub>3<\/sub> (including other phosphorus halides) and SOCl<sub>2<\/sub>.<\/p>\n<p><strong>Next Post &#8211; <a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/03\/20\/pbr3-and-socl2\/\">PBr<sub>3\u00a0<\/sub>And SOCl<sub>2<\/sub><\/a><\/strong><\/p>\n<hr \/>\n<h2><a id=\"notes\"><\/a>Notes<\/h2>\n<div class=\"related-articles\"><p><strong>Related Articles<\/strong><\/p><ul><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/03\/20\/pbr3-and-socl2\/\" class=\"\"><span>PBr3 and SOCl2<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/04\/12\/what-makes-a-good-leaving-group\/\" class=\"\"><span>What makes a good leaving group?<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/06\/18\/what-makes-a-good-nucleophile\/\" class=\"\"><span>What Makes A Good Nucleophile?<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/07\/04\/the-sn2-mechanism\/\" class=\"\"><span>The SN2 Mechanism<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/02\/27\/making-alkyl-halides-from-alcohols\/\" class=\"\"><span>Making Alkyl Halides From Alcohols<\/span><\/a><\/li><\/ul><\/div>\n<hr \/>\n<h2><a id=\"quizzes\"><\/a>Quiz Yourself!<\/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\/1347-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\/1349-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\/1351-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\/1352-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\/1354-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\/1375-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 Further Reading<\/strong><\/h2>\n<ol>\n<li><strong>ON ESTERS OF p-TOLUENESULFONIC ACID<br \/>\n<\/strong> STUART TIPSON<br \/>\n<em>The Journal of Organic Chemistry,\u00a0<\/em><strong>1944,\u00a0<\/strong><em>09\u00a0<\/em>(3), 235-241<br \/>\n<strong>DOI:\u00a0<\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jo01185a005\">10.1021\/jo01185a005<\/a><br \/>\nEarly reference on tosylation by Stuart Tipson, who was at the Mellon Institute of Industrial Research (now Carnegie-Mellon University).<\/li>\n<li><strong>The tosylation of alcohols<br \/>\n<\/strong>George W. Kabalka, Manju Varma, Rajender S. Varma, Prem C. Srivastava, and Furn F. Knapp Jr.<br \/>\n<em>The Journal of Organic Chemistry,\u00a0<\/em><strong>1986,\u00a0<\/strong><em>51\u00a0<\/em>(12), 2386-2388<strong><br \/>\nDOI:\u00a0<\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/jo00362a044\">10.1021\/jo00362a044<\/a><br \/>\nThis paper describes an improved procedure for tosylation of alcohols.Besides the <em>p\u00ad-<\/em>toluenesulfonyl group, other sulfonate esters can be prepared as leaving groups from alcohols (e.g. mesylate, brosylate, triflate, trifluoroacetate, nonaflate, etc.). Two papers describing mesylate ester synthesis are described below:<\/li>\n<li><strong>Kinetic and spectroscopic characterisation of highly reactive methanesulfonates. Leaving group effects for solvolyses and comments on geminal electronic effects influencing SN1 reactivity<\/strong><br \/>\nWilliam Bentley, Manfred Christl, Ralf Kemmer, Gareth Llewellyn and John E. Oakley<br \/>\n<em>J. Chem. Soc., Perkin Trans. 2<\/em>, <strong>1994<\/strong>, 2531-2538<br \/>\n<strong>DOI:\u00a0<\/strong><a href=\"https:\/\/pubs.rsc.org\/en\/content\/articlelanding\/1994\/p2\/p29940002531#!divAbstract\">10.1039\/P29940002531<\/a><\/li>\n<li><strong>Palladium-catalyzed Buchwald-Hartwig Amination and Suzuki-Miyaura Cross-coupling Reaction of Aryl Mesylates<br \/>\n<\/strong>Shun Man Wong, Pui Ying Choy, On Ying Yuen, Chau Ming So, and Fuk Yee Kwong<br \/>\n<em> Synth.<\/em><strong>2015<\/strong>, <em>92<\/em>, 195-212<br \/>\n<strong>DOI:\u00a0<\/strong><a href=\"http:\/\/orgsyn.org\/demo.aspx?prep=v92p0195\">10.15227\/orgsyn.092.0195<\/a><br \/>\nThe first step in this procedure is the mesylation of <em>p<\/em>-t-butylphenol.<\/li>\n<li><strong>Synthesis of some novel trifluoromethanesulfonates and their reactions with alcohol<br \/>\n<\/strong>Charles D. Beard, Kurt Baum, and Vytautas Grakauskas<br \/>\n<em>The Journal of Organic Chemistry,\u00a0<\/em><strong>1973,\u00a0<\/strong><em>38\u00a0<\/em>(21), 3673-3677<br \/>\n<strong>DOI:\u00a0<\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/jo00961a003\">10.1021\/jo00961a003<\/a><br \/>\nTriflate (-SO<sub>2<\/sub>CF<sub>3<\/sub>) esters are much more reactive than tosylates or mesylates, since the triflate anion is a superb leaving group. This paper describes the synthesis of various triflate esters but gives no mention for safety considerations \u2013 these are potent alkylating agents and are highly carcinogenic.<\/li>\n<\/ol>\n","protected":false},"excerpt":{"rendered":"<p>All About Tosylates and Mesylates By themselves, alcohols are poor leaving groups since the hydroxide ion (HO-) is a strong base The OH group can <\/p>\n","protected":false},"author":1,"featured_media":15196,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1420],"tags":[473,226,1051,1053,254,271,279,1055,1052,1054],"post_folder":[],"class_list":["post-8806","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-alcohols-epoxides-ethers","tag-e2","tag-leaving-groups","tag-mesylate","tag-ms","tag-pka","tag-sn2","tag-substitution","tag-sultanate","tag-tosylate","tag-ts"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Tosylates And Mesylates &#8211; Master Organic Chemistry<\/title>\n<meta name=\"description\" content=\"One way to convert alcohols to good leaving groups is to convert to a sulfonate ester like OTs (&quot;tosyl&quot;) or OMs (&quot;mesyl&quot;). Tosylate (TsO-) is a great LG.\" \/>\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\/2015\/03\/10\/tosylates-and-mesylates\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Tosylates And Mesylates &#8211; Master Organic Chemistry\" \/>\n<meta property=\"og:description\" content=\"One way to convert alcohols to good leaving groups is to convert to a sulfonate ester like OTs (&quot;tosyl&quot;) or OMs (&quot;mesyl&quot;). 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