{"id":8519,"date":"2014-10-17T15:40:26","date_gmt":"2014-10-17T19:40:26","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=8519"},"modified":"2026-05-03T07:49:21","modified_gmt":"2026-05-03T12:49:21","slug":"alcohols-acidity-and-basicity","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2014\/10\/17\/alcohols-acidity-and-basicity\/","title":{"rendered":"Alcohols &#8211; Acidity and Basicity"},"content":{"rendered":"<p><strong>Acid-Base Reactions Of Alcohols<\/strong><\/p>\n<p>Alcohols are mild <strong>acids. <\/strong>\u00a0Typical aliphatic (i.e. &#8220;alkyl&#8221;) alcohols such as ethanol, isopropanol, and\u00a0<em>t<\/em>-butanol have a pK<sub>a<\/sub> of about 16-18, making them slightly more acidic than water.<\/p>\n<ul>\n<li>Alcohols that are in <strong>conjugation<\/strong> with a pi bond or aromatic ring will be <strong>more acidic<\/strong> since the conjugate base is resonance-stabilized. One key example is phenol (C<sub>6<\/sub>H<sub>5<\/sub>OH). (pK<sub>a<\/sub> = 10).<\/li>\n<li>Nearby electron-withdrawing groups will stabilize the negative charge of the conjugate base through inductive effects. For example, 2,2,2-trifluoroethanol (pK<sub>a<\/sub> = 12) is considerably more acidic than ethanol (pK<sub>a<\/sub> = 16).<\/li>\n<\/ul>\n<p>Alcohols are also weak <strong>bases<\/strong>. They can react with strong acids to give <strong>oxonium ions<\/strong> which have a pK<sub>a<\/sub> of about -2.<\/p>\n<p>One of the keys to the reactions of alcohols as we go forward is that the <strong>conjugate acid is a better leaving group<\/strong> and the <strong>conjugate base is a better nucleophile.<\/strong><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">Four Key Points To Review About Acid-Base Reactions<\/a><\/li>\n<li><a href=\"#two\">Favorable and Unfavorable Acid-Base Reactions of Alcohols (2 Examples)<\/a><\/li>\n<li><a href=\"#three\">Reviewing The Key Factors Which Determine Acidity<\/a><\/li>\n<li><a href=\"#four\">Applying These Factors To The Acidity of Alcohols<\/a><\/li>\n<li><a href=\"#five\">A Practice Question<\/a><\/li>\n<li><a href=\"#six\">Summary: Acidity and Basicity of Alcohols<\/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<hr \/>\n<h2><strong><a id=\"one\"><\/a>1. Four Key Points To Review About Acid\u00a0Base Reactions<\/strong><\/h2>\n<ol>\n<li><strong>Every acid-base reaction has 4 components<\/strong>: an <strong>acid<\/strong>, a <strong>base<\/strong>, a <strong>conjugate acid<\/strong>, and a <strong>conjugate base<\/strong>.When an acid loses a proton, it becomes its conjugate base. When a base gains a proton, it becomes its conjugate acid. As mentioned in the previous post, the conjugate bas of an alcohol is called an<strong> alkoxide<\/strong>. The conjugate acid of an alcohol is called an<strong> oxonium ion<\/strong>. (<em>See post: <a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/04\/11\/walkthrough-of-acid-base-reactions-1\/\">Acid-Base Reactions in Organic Chemistry<\/a><\/em>)<\/li>\n<li>We usually describe acid-base reactions as an equilibrium. In acid-base reactions, the<strong> equilibrium will favor the direction where a stronger acid and stronger base produces\u00a0a weaker acid and a weaker base<\/strong>.When you add HCl to NaOH, a violent acid-base reaction occurs, which leads to the formation of H<sub>2<\/sub>O (a weaker acid than HCl) and NaCl (a weaker base than NaOH). As you&#8217;ve no doubt discovered when adding table salt (NaCl) to water, this reaction doesn&#8217;t proceed to any significant extent in the reverse direction.<\/li>\n<li>We measure acidity using a term called pK<sub>a<\/sub>. This is a measure of the <strong><strong>equilibrium constant for a species giving up a proton to form its conjugate base. <\/strong><\/strong>\u00a0pK<sub>a<\/sub> is on a scale of about -10 to 50. <strong>Sixty orders of magnitude!<\/strong>\u00a0 The higher the pK<sub>a<\/sub> the less acidic it is. \u00a0Lower pK<sub>a<\/sub> (more negative ) = more acidic.<br \/>\nWater (pK<sub>a<\/sub> of 14.0) is a weaker acid than HCl (pK<sub>a<\/sub> of -8).\u00a0<em>(See article: <a href=\"https:\/\/www.masterorganicchemistry.com\/2010\/09\/29\/how-to-use-a-pka-table\/\">How To Use a pK<sub>a<\/sub> Table<\/a>)<\/em><\/li>\n<li>\u00a0<strong>The stronger the acid, the weaker the conjugate base. The weaker the acid, the stronger the conjugate base.\u00a0<\/strong>The conjugate base of the strong acid HCl (pK<sub>a<\/sub> -8) is the innocuous chloride ion (Cl-), a very weak base. The conjugate base of the weak acid H<sub>2<\/sub>O (pK<sub>a<\/sub> 14) is the strongly basic hydroxide ion (HO-).<\/li>\n<\/ol>\n<h2><strong><a id=\"two\"><\/a>2. Examples of Acid-Base Reactions Of Alcohols<\/strong><\/h2>\n<p>Here\u2019s an example of a <strong>favorable<\/strong> acid-base reaction of alcohols. Note how we&#8217;re going from a stronger acid and stronger base to a weaker acid and weaker base [pK<sub>a<\/sub> values tell us for sure]<\/p>\n<p>Here, deprotonation is very favourable. Note that the conjugate base of an alcohol is called an alkoxide.<\/p>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-26296\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2022\/08\/1-acid-base-reaction-of-alcohols-favorable-with-nanh2-stronger-acid-stronger-base-gives-weaker-acid-weaker-base.gif\" alt=\"acid base reaction of alcohols favorable with nanh2 stronger acid stronger base gives weaker acid weaker base\" width=\"630\" height=\"274\" \/><\/a><\/p>\n<p>Here\u2019s an example of a (very) <strong>unfavorable<\/strong> acid-base reaction of alcohols: protonation of an alcohol by NH<sub>3<\/sub>. The most important reason why this is unfavourable is because we&#8217;re going from a weaker acid (pK<sub>a<\/sub> 38) and weaker base to a stronger acid (pK<sub>a<\/sub> -2) and stronger base. The equilibrium constant is about 40 orders of magnitude in the <strong>wrong<\/strong> direction!<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-26297\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2022\/08\/2-unfavorable-acid-base-reaction-of-alcohols-is-deprotonation-of-nh3-by-alcohol-to-give-oxonium-and-nanh2-weaker-acid-gives-stronger-acid-unfavorable.gif\" alt=\"unfavorable acid base reaction of alcohols is deprotonation of nh3 by alcohol to give oxonium and nanh2 weaker acid gives stronger acid unfavorable\" width=\"630\" height=\"266\" \/><\/a><\/p>\n<h2><strong><a id=\"three\"><\/a>3. Reviewing The Key Factors That Determine Acidity\u00a0<\/strong><\/h2>\n<p>What determines how acidic a molecule is, anyway?<\/p>\n<p>The key factor in determining acidity <strong>is the stability of the conjugate base<\/strong>. Any factor which makes the conjugate base more stable will increase the acidity of the acid. (<em>See post: <a href=\"https:\/\/www.masterorganicchemistry.com\/2010\/09\/22\/five-key-factors-that-influence-acidity\/\">5 Key Factors Which Influence Acidity<\/a><\/em>)<\/p>\n<p>What does that mean, exactly? Usually, it means\u00a0<strong>stabilizing negative charge\u00a0<\/strong>since the conjugate base will always be one unit of charge more &#8220;negative&#8221; than the acid. (<em>See post: <a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/02\/27\/7-factors-that-stabilize-negative-charge-in-organic-chemistry\/\">7 Factors That Stabilize Negative Charge<\/a><\/em>)<\/p>\n<p>How is negative charge stabilized?\u00a0<strong>Two ways<\/strong>.<\/p>\n<ul>\n<li>First, by bringing the charge closer to the positively charged nucleus [&#8220;opposite charges attract&#8221;, remember]. <strong>Across a row<\/strong> of the periodic table, for example, basicity decreases as we go from H<sub>3<\/sub>C<sup>&#8211;<\/sup> to H<sub>2<\/sub>N<sup>&#8211;<\/sup> to HO<sup>&#8211;<\/sup> to F<sup>&#8211;<\/sup> \u00a0because <strong>the electronegativity of the atom is increasing<\/strong>. That negative charge is being held closer to the nucleus, and therefore is more stable. A good rule of thumb is, &#8220;the more stable a lone pair, the less basic it is. This is also why<strong> certain species are made acidic by adjacent electron-withdrawing groups.<\/strong><\/li>\n<li>Second, <strong>by spreading charge out over a larger volume<\/strong>. Diffuse charge is more stable than concentrated charge. Down a row of the periodic table, for example, basicity decreases\u00a0as we go from F<sup>&#8211;<\/sup>\u00a0to Cl<sup>&#8211;<\/sup>\u00a0to Br<sup>&#8211;<\/sup>\u00a0to I<sup>&#8211;\u00a0<\/sup>because that negative charge is being spread out over a larger volume (larger atoms). The larger atoms are said to be more &#8220;polarizable&#8221;. [Note that this effect dominates rather than electronegativity in this case.] This is also why\u00a0<strong>resonance<\/strong> serves to stabilize charges; the charge is being spread across multiple atoms, therefore reducing individual charge density. (<em>See post: <a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/12\/22\/in-summary-resonance\/\">In Summary &#8211; Resonance<\/a><\/em>)<\/li>\n<\/ul>\n<h2><strong><a id=\"four\"><\/a>4. Applying These Principles To The Acidity Of Alcohols<\/strong><\/h2>\n<p>How do these principles relate to alcohols? It&#8217;s quite simple, actually. Since we&#8217;ll always be comparing the same atom (oxygen) we don&#8217;t need to worry about periodic trends, and we just need to focus on <b>resonance<\/b> and\u00a0<strong>adjacent electron-withdrawing groups<\/strong>.<\/p>\n<p>Alcohols where the conjugate base is\u00a0<strong>resonance stabilized\u00a0<\/strong>will be <strong>more<\/strong> <strong>acidic<\/strong>. The classic example is\u00a0cyclohexanol and phenol.<\/p>\n<p>Cyclohexanol has the pK<sub>a<\/sub> of a typical alcohol (about 16). The pK<sub>a<\/sub> of phenol, however, is about <strong>10<\/strong>. Let&#8217;s look:<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-26298\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2022\/08\/3-what-is-more-acidic-phenol-or-cyclohexanol-phenol-more-acidic-because-conjugate-base-more-stable-due-to-resonance.gif\" alt=\"what is more acidic phenol or cyclohexanol phenol more acidic because conjugate base more stable due to resonance\" width=\"630\" height=\"276\" \/><\/a><\/p>\n<p>See how that negative charge on the oxygen of phenol can be &#8220;delocalized&#8221; back into the ring? That means the charge can be spread out throughout the molecule, which is stabilizing.\u00a0<strong>Any factor which stabilizes the conjugate base will increase acidity.\u00a0<\/strong><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15121\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/4-resonance-forms-of-conjugate-base-of-phenol-shows-4-resonance-forms-delocallized-charge-more-stable.gif\" alt=\"resonance forms of conjugate base of phenol shows 4 resonance forms delocallized charge more stable\" width=\"600\" height=\"139\" \/><\/p>\n<p>Here&#8217;s another example. Compare ethanol (pK<sub>a<\/sub> 16) to 2,2,2-trifluoroethanol (pK<sub>a<\/sub> about 12). Why do you think trifluoroethanol is more acidic?<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26299\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2022\/08\/5-what-is-more-acidic-ethanol-or-trifluoroethanol-electronegative-atoms-give-inductive-effect-stabilizes-negative-charge-in-conjugate-base-of-trifluoroethanol.gif\" alt=\"what is more acidic ethanol or trifluoroethanol electronegative atoms give inductive effect stabilizes negative charge in conjugate base of trifluoroethanol\" width=\"630\" height=\"301\" \/><\/a><\/p>\n<p>Compare their conjugate bases.\u00a0What is fluorine doing here to make the conjugate base more stable?<\/p>\n<p>This is an example of an <strong>inductive effect.\u00a0<\/strong>Fluorine, being highly electronegative, pulls electron density away from the neighbouring carbon. That carbon, now being electron poor, pulls electron density away from the carbon next door. And that carbon, being slightly electron poor, can pull some electron density away from the oxygen.<\/p>\n<p>The net result is that the oxygen has lower electron density, which is stabilizing. Again,\u00a0<strong>stabilize the conjugate base &#8211;&gt; \u00a0increase acidity.\u00a0<\/strong><\/p>\n<p>(S<em>ee post:<\/em> <a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/04\/16\/walkthrough-of-acid-base-reactions-2-basicity\/\"><em>The Stronger The Acid, The Weaker The Conjugate Base<\/em><\/a>)<\/p>\n<p>This also works if we compare alcohol variations where we change the distance between the OH and the fluorine atom.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15123\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/6-inductive-effect-of-alcohols-decreases-as-distance-from-acid-is-increased-acidity-differences-fluoride-alcohols.gif\" alt=\"inductive effect of alcohols decreases as distance from acid is increased acidity differences fluoride alcohols\" width=\"600\" height=\"153\" \/><\/p>\n<p>That&#8217;s because the inductive effect decreases in magnitude the farther away we go from the electronegative atom.<\/p>\n<p>We can also use electronegativity trends to determine the order of acidity in these molecules. Since fluorine is more electronegative than chlorine which is more electronegative than bromine which is more electronegative than iodine, the inductive effect will be highest for CF<sub>3<\/sub> and lowest for CI<sub>3<\/sub>.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15124\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/7-inductive-effect-increases-increasing-electrnegativity-trifluoro-most-acidic-triiodo-least-acidic-less-electronegativity.gif\" alt=\"inductive effect increases increasing electrnegativity trifluoro most acidic triiodo least acidic less electronegativity\" width=\"600\" height=\"169\" \/><\/p>\n<h2><a id=\"five\"><\/a>5. A Practice Question<\/h2>\n<p>Finally, one last example. We can even think of examples where these two effects are combined:<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"39002\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"39002\"] {\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=\"39002\"] {\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=\"39002\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-39002\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-39002 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"39002\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-25i4g\" data-id=\"25i4g\">\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\/2305-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\/2305-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>Which do you think might be most acidic here?<\/p>\n<h2><b><a id=\"six\"><\/a>6. Summary: Acidity Of Alcohols<\/b><\/h2>\n<p>Now that we&#8217;ve covered the key factors governing the acidity of alcohols, we&#8217;re more prepared to get into the nitty gritty of their different reactions. In the next post we&#8217;ll start discussing how acidity and basicity affects the reaction conditions we can use.<\/p>\n<p>For alcohols, since we\u2019re always dealing with oxygen, the only relevant factors here are <strong>resonance<\/strong> and <strong>electron withdrawing groups<\/strong>.<\/p>\n<p><strong>Next Post &#8211; <a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/10\/24\/the-williamson-ether-synthesis\/\">The Williamson Ether Synthesis<\/a>\u00a0<\/strong><\/p>\n<hr \/>\n<h2><strong>Notes<\/strong><\/h2>\n<div class=\"related-articles\"><p><strong>Related Articles<\/strong><\/p><ul><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\/2010\/09\/29\/how-to-use-a-pka-table\/\" class=\"\"><span>How to Use a pKa Table<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/05\/09\/acid-base-reactions-ka-and-pka\/\" class=\"\"><span>Acid-Base Reactions: Introducing Ka and pKa<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/04\/16\/walkthrough-of-acid-base-reactions-2-basicity\/\" class=\"\"><span>The Stronger The Acid, The Weaker The Conjugate Base<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2010\/09\/22\/five-key-factors-that-influence-acidity\/\" class=\"\"><span>Five Key Factors That Influence Acidity<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/02\/27\/7-factors-that-stabilize-negative-charge-in-organic-chemistry\/\" class=\"\"><span>7 Factors that stabilize negative charge in organic chemistry<\/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\/04\/16\/walkthrough-of-acid-base-reactions-2-basicity\/\" class=\"\"><span>The Stronger The Acid, The Weaker The Conjugate Base<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/10\/06\/how-to-make-alcohols-more-reactive\/\" class=\"\"><span>Alcohols Can Act As Acids Or Bases (And Why It Matters)<\/span><\/a><\/li><\/ul><\/div>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-45805\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2026\/05\/T7-Summary-pka-values-of-alcohols-and-thiols-primary-secondary-tertiary-alcohol-pka-substituted-phenol-pka.gif\" alt=\"Summary-pka values of alcohols and thiols primary secondary tertiary alcohol pka substituted phenol pka\" width=\"640\" height=\"708\" \/><\/a><\/p>\n<hr \/>\n<h2><a id=\"quiz\"><\/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\/0570-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\/0571-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\/0572-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\/0263-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\/0280-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\/2313-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<p>&nbsp;<\/p>\n<h2><a id=\"references\"><\/a>(Advanced) References and Further Reading<\/h2>\n<p><strong>1.\u00a0 Collected Acidity-Basicity Data<\/strong><br \/>\n<a href=\"https:\/\/analytical.chem.ut.ee\/HA_UT\/\">This website<\/a> from the University of Estonia has a large curated list of studies on the acidity and basicity of various organic compounds.<\/p>\n<p>Here is a leading reference. These pK<sub>a<\/sub> values refer to acetonitrile as solvent, so will be substantially different from those measured in aqueous solution, although the overall trends will be the same.<\/p>\n<p><strong>2. Strengths of Acids in Acetonitrile<br \/>\n<\/strong>A. K\u00fctt, S. Tshepelevitsh, J. Saame, M. L\u00f5kov, I. Kaljurand, S. Selberg, I. Leito<br \/>\n<i>Eur. J. Org. Chem.<\/i>\u00a0<b>2021<\/b>,\u00a0<i>2021<\/i>, 1407.<br \/>\n<strong>DOI: <\/strong><a href=\"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/epdf\/10.1002\/ejoc.202001649\">doi.org\/10.1002\/ejoc.202001649<\/a><\/p>\n<p>(Open access)<\/p>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Acid-Base Reactions Of Alcohols Alcohols are mild acids. \u00a0Typical aliphatic (i.e. &#8220;alkyl&#8221;) alcohols such as ethanol, isopropanol, and\u00a0t-butanol have a pKa of about 16-18, making <\/p>\n","protected":false},"author":1,"featured_media":15118,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1420],"tags":[1021,163,167,688,586,1022,254,336,267],"post_folder":[],"class_list":["post-8519","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-alcohols-epoxides-ethers","tag-acid-base-reactions","tag-acidity","tag-alcohols","tag-conjugate-acid","tag-conjugate-base","tag-inductive-effect","tag-pka","tag-polarizability","tag-resonance"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Acidity and Basicity of Alcohols &#8211; 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