{"id":8509,"date":"2014-10-06T13:19:29","date_gmt":"2014-10-06T17:19:29","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=8509"},"modified":"2022-11-04T05:12:21","modified_gmt":"2022-11-04T10:12:21","slug":"how-to-make-alcohols-more-reactive","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2014\/10\/06\/how-to-make-alcohols-more-reactive\/","title":{"rendered":"Alcohols Can Act As Acids Or Bases (And Why It Matters)"},"content":{"rendered":"<p><strong>Alcohols: The Conjugate Acid Is A Better Leaving Group, and The Conjugate Base Is A Better Nucleophile<\/strong><\/p>\n<p>In the last post we\u00a0explored\u00a0some of the\u00a0<a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/09\/17\/alcohols-1-nomenclature-and-properties\/\">properties and nomenclature of alcohols<\/a>. We said that alcohols tend to have high boiling points due to hydrogen bonding, and that\u00a0 we commonly divide alcohols into the categories\u00a0 \u201cprimary\u201d, \u201csecondary\u201d,\u00a0 and \u201ctertiary\u201d (with a nod to the unique, \u201cmethanol\u201d) according to how many carbons are attached to the C bearing the hydroxyl group.<\/p>\n<p>Now that we\u2019ve dipped our toe in the a little bit, we\u2019re going to start looking at the <strong>key reactions<\/strong> of alcohols. We\u2019re going to begin in this post by discussing <b>acid base reactions <\/b>of alcohols. As we\u2019ll see, these reactions really \u201cset up\u201d a lot of the reactions we\u2019ll later see in this section.<\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">Reviewing Two Earlier Reactions of Alcohols<\/a><\/li>\n<li><a href=\"#two\">Neutral Alcohols Only Tend To Undergo Reactions With Very Reactive Electrophiles<\/a><\/li>\n<li><a href=\"#three\">The Conjugate Acid of An Alcohol Is A Better Electrophile<\/a><\/li>\n<li><a href=\"#four\">The Conjugate Base of An Alcohol Is A Better Nucleophile<\/a><\/li>\n<li><a href=\"#five\">Summary: Making Alcohols More Reactive<\/a><\/li>\n<li><a href=\"#notes\">Notes<\/a><\/li>\n<\/ol>\n<hr \/>\n<h2><a id=\"one\"><\/a>1. Reviewing Two Earlier Reactions Of Alcohols: Addition To Carbocations And To Halonium Ions<\/h2>\n<p>Before going there, however, let\u2019s just review the reactions of alcohols we\u2019ve already seen that aren\u2019t explicitly acid base reactions. There are really <strong>only two.\u00a0<\/strong><\/p>\n<ul>\n<li>First, we\u2019ve seen that <strong>alcohols will react with carbocations to give ethers<\/strong>. The carbocation can either come from protonation of an alkene (path 1) or from \u201cionization\u201d (that is, loss of a good leaving group) of an alkyl halide or similar starting material. This latter reaction falls into the category of S<sub>N<\/sub>1 reactions.<\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-15117\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-ether-synthesis-alcohols-react-with-carbocations-to-give-ethers.gif\" alt=\"ether synthesis alcohols react with carbocations to give ethers\" width=\"600\" height=\"385\" \/><\/p>\n<ul>\n<li>Secondly, we\u2019ve also seen that reactive, positively charged, 3-membered ring intermediates such as halonium ions and mercurinium ions <strong>can also be attacked by alcohols at the most substituted carbon\u00a0<\/strong> (<span style=\"color: #993366;\"><em>\u201cMarkovnikov\u201d addition<\/em><\/span>) to give \u201chalo ethers\u201d (for halonium ions) and ethers ( if we use Hg(OAc)<sub>2<\/sub> and then\u00a0add\u00a0\u00a0NaBH<sub>4<\/sub>). Note that alcohol is the solvent here.<\/li>\n<\/ul>\n<p><img decoding=\"async\" class=\"alignnone wp-image-15114\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-alcohols-react-with-halonium-ions-bromonium-ion-chloronium-ion-to-give-haloethers-markovnikov-addition.gif\" alt=\"alcohols react with halonium ions bromonium ion chloronium ion to give haloethers markovnikov addition\" width=\"600\" height=\"281\" \/><\/p>\n<h2><a id=\"two\"><\/a>2. Neutral Alcohols Only Tend To Undergo Reactions With Extremely Reactive Electrophiles<\/h2>\n<p>Do you notice something that both of these reactants [carbocations and \u201c3 membered ring\u201d intermediates] have in common?<b> They\u2019re both extremely reactive\u00a0<\/b>electrophiles.<\/p>\n<p>Getting alcohols to act as nucleophiles is a little like trying to get pandas to mate in a zoo. It only happens if the female (electrophile) is incredibly horny. <a href=\"http:\/\/mentalfloss.com\/article\/12610\/why-it-so-hard-pandas-get-pregnant\">That\u2019s not too often, apparently<\/a>.\u00a0<strong><a href=\"#noteone\">Note 1<\/a>.\u00a0<\/strong><\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-15115\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-pandas-are-hard-to-induce-to-have-sex-jjust-like-ethers-are-reluctant-to-react-with-functional-groups.jpg\" alt=\"pandas are hard to induce to have sex jjust like ethers are reluctant to react with functional groups\" width=\"450\" height=\"311\" srcset=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-pandas-are-hard-to-induce-to-have-sex-jjust-like-ethers-are-reluctant-to-react-with-functional-groups.jpg 600w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-pandas-are-hard-to-induce-to-have-sex-jjust-like-ethers-are-reluctant-to-react-with-functional-groups-300x208.jpg 300w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-pandas-are-hard-to-induce-to-have-sex-jjust-like-ethers-are-reluctant-to-react-with-functional-groups-320x221.jpg 320w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-pandas-are-hard-to-induce-to-have-sex-jjust-like-ethers-are-reluctant-to-react-with-functional-groups-360x249.jpg 360w\" sizes=\"(max-width: 450px) 100vw, 450px\" \/><\/p>\n<p>As for hydroxyl groups as leaving groups, forget it. We\u2019ve seen that in order for a leaving group to leave in S<sub>N<\/sub>2 and E2 reactions, it has to be a fairly weak base. (<em>See post: <a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/04\/12\/what-makes-a-good-leaving-group\/\">What Makes A Good Leaving Group<\/a><\/em>). The hydroxy (HO-)\u00a0 and alkoxy (RO -) groups are both fairly <strong>strong<\/strong> bases, and therefore <strong>poor<\/strong> leaving groups.<\/p>\n<p>The bottom line here is that the hydroxyl groups of R\u2013OH are not particularly reactive nucleophiles or electrophiles, <b>as themselves<\/b>.<\/p>\n<p>But, like frustrated zookeepers must have wondered at some point: can\u2019t we find some kind of aphrodisiac that can speed up the process?<\/p>\n<p>While I am currently unaware of progress on the panda aphrodisiac front, I can tell you that it is actually quite straightforward to make alcohols more reactive.<\/p>\n<p>Think about\u00a0 two concepts we\u2019ve explored previously. <b>Leaving group ability<\/b> and <b>nucleophilicity.\u00a0<\/b><\/p>\n<h2><b><a id=\"three\"><\/a>3. The Conjugate Acid Of An Alcohol Has A Better Leaving Group (and is therefore a better electrophile)<\/b><\/h2>\n<p>Hydroxyl groups (HO-)\u00a0 are poor l<b>eaving groups<\/b> because they\u2019re <b>strong bases<\/b>.<\/p>\n<p>However, if we protonate them (add acid), then we get an oxonium ion (R-OH<sub>2<\/sub>+). The leaving group is now H<sub>2<\/sub>O &#8211; a <b>weak base<\/b> and a <b>great leaving group.<\/b> The oxonium ion is much better set up to participate in reactions such as the S<sub>N<\/sub>1 and E1, as well as (more rarely) the S<sub>N<\/sub>2 and E2.<\/p>\n<p>So a simple reaction with an acid converts a relatively boring alcohol R\u2013OH into a species with a much better leaving group, R\u2013OH<sub>2<\/sub>(+).<\/p>\n<p>Since a protonated alcohol has a better leaving group, this also makes it a much better electrophile as well.<\/p>\n<p>The conjugate acid is a better leaving group!<\/p>\n<h2><a id=\"four\"><\/a>4. The Conjugate Base Of An Alcohol Is A Better Nucleophile<\/h2>\n<p>Hydroxyl groups in R\u2013OH are <b>poor nucleophiles<\/b> because they\u2019re neutral and the electron pair is held tightly to the oxygen.<\/p>\n<p>However, if we remove a proton (by adding a base) we then get an<b> alkoxide ion<\/b> (RO-)\u00a0 which has much higher electron density, and <b>is a much better nucleophile<\/b> (as well as being a strong base). Alkoxide ions are far more reactive in substitution reactions (S<sub>N<\/sub>2) than neutral alcohols, and because they are far more basic than neutral alcohols, more reactive in the E2 reaction as well.<\/p>\n<p>So simple treatment with base converts a relatively boring alcohol into the excellent nucleophile (and strong base) RO(\u2013).<\/p>\n<p>The conjugate base is a better nucleophile!<\/p>\n<h2><a id=\"five\"><\/a>5. Summary: Making Alcohols More Reactive<\/h2>\n<p>Adding or removing a proton can have a drastic effect on the reactivity of an alcohol.<\/p>\n<p>Here&#8217;s a summary image:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15116\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/4-alcohol-reaction-with-aci-gives-better-leaving-group-conjugate-acid-better-electrophile-conjugate-base-of-alcohol-better-nucleophile-reaction-with-base-does-sn2.gif\" alt=\"alcohol reaction with aci gives better leaving group conjugate acid better electrophile conjugate base of alcohol better nucleophile reaction with base does sn2\" width=\"600\" height=\"454\" \/><\/p>\n<p>So the bottom line for this post is that converting an alcohol into its conjugate acid makes it a better leaving group (setting up S<sub>N<\/sub>1 and E1 reactions, mostly) while converting an alcohol into its conjugate base makes it a better nucleophile (setting up the S<sub>N<\/sub>2) and a better base (setting up the E2).<\/p>\n<p>This is old news &#8211; \u201c<a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/08\/07\/the-conjugate-acid-is-a-better-leaving-group\/\">the conjugate acid is always a better leaving group<\/a>\u201d, and \u201c<a href=\"https:\/\/www.masterorganicchemistry.com\/2010\/04\/19\/the-conjugate-base-is-always-a-stronger-nucleophile\/\">the conjugate base is always a better nucleophile<\/a>\u201d &#8211; but worth drawing attention to again, because <b>we\u2019ll see these patterns again and again in reactions of alcohols<\/b>.<\/p>\n<p>In the next post, we\u2019re going to go into these acid-base reactions of alcohols in slightly more detail, and use what we learn to figure out the limits of how we can apply these concepts to substitution and elimination reactions.<\/p>\n<p><strong>Next Post: <a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/10\/17\/alcohols-3-acidity-and-basicity\/\">Alcohols (3) &#8211; Acidity And Basicity<\/a><\/strong><\/p>\n<hr \/>\n<h2><a id=\"notes\"><\/a>Notes<\/h2>\n\n<p><strong><a id=\"noteone\"><\/a>Note 1. <\/strong>\u00a0Rare but it apparently does happen. <a href=\"https:\/\/www.youtube.com\/watch?v=9xQEwytm6RU&amp;index=2&amp;list=PL12A1C24328D8CC59\" target=\"_blank\" rel=\"noopener noreferrer\">NSFW (especially if you are a panda) link to a happy couple\u00a0at the Washington Zoo<\/a><\/p>\n","protected":false},"excerpt":{"rendered":"<p>Alcohols: The Conjugate Acid Is A Better Leaving Group, and The Conjugate Base Is A Better Nucleophile In the last post we\u00a0explored\u00a0some of the\u00a0properties and <\/p>\n","protected":false},"author":1,"featured_media":15117,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1420],"tags":[688,586,841,825],"post_folder":[],"class_list":["post-8509","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-alcohols-epoxides-ethers","tag-conjugate-acid","tag-conjugate-base","tag-leaving-group","tag-nucleophile"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Alcohols Can Act As Acids Or Bases (And Why It Matters)<\/title>\n<meta name=\"description\" content=\"Are alcohols acids or bases? 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