{"id":4934,"date":"2012-04-11T09:16:01","date_gmt":"2012-04-11T09:16:01","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=4934"},"modified":"2025-10-28T11:45:34","modified_gmt":"2025-10-28T16:45:34","slug":"walkthrough-of-acid-base-reactions-1","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2012\/04\/11\/walkthrough-of-acid-base-reactions-1\/","title":{"rendered":"Acid Base Reactions In Organic Chemistry"},"content":{"rendered":"<p><strong>An Introduction to Acid Base Reactions In Organic Chemistry<\/strong><\/p>\n<p>Now that we&#8217;ve described how to figure out <a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/01\/17\/how-to-apply-electronegativity-and-resonance-to-understand-reactivity\/\">where the electrons are in a molecule<\/a>, \u00a0the factors that stabilize <a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/02\/27\/7-factors-that-stabilize-negative-charge-in-organic-chemistry\/\">negative charge <\/a>and <a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/03\/07\/7-factors-that-stabilize-positive-charge-in-organic-chemistry\/\">positive charge<\/a>, and gone into the <a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/02\/15\/curved-arrows-for-reactions\/\">curved arrow formalism<\/a> for reactions, we&#8217;re ready to start going into more detail on some of the key reactions in organic chemistry.<\/p>\n<p>After reading this article, you should be able to:<\/p>\n<ul>\n<li>Identify the\u00a0<strong>acid, base, conjugate acid <\/strong>and<strong> conjugate base\u00a0<\/strong>in each acid-base reaction.<\/li>\n<li>Understand the relationship between acidity and the stability of the conjugate base<\/li>\n<li>Understand some of the key factors which stabilize a conjugate base<\/li>\n<li>Given a knowledge of pK<sub>a<\/sub> values, identify the direction in which an acid-base equilibrium is favored.<\/li>\n<\/ul>\n<p>You can test your understanding using the <a href=\"#quizzes\"><strong>quizzes<\/strong><\/a> at the bottom of this article.<\/p>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-37419\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2024\/10\/0-summary-acid-base-reactions-conjugate-acid-conjugate-base-stronger-acid-weaker-conjugate-base.gif\" alt=\"summary acid base reactions conjugate acid conjugate base stronger acid weaker conjugate base\" width=\"640\" height=\"571\" \/><\/a><\/p>\n<p><strong>Table Of Contents<\/strong><\/p>\n<ol>\n<li class=\"p1\"><a href=\"#one\"><span class=\"s1\">The Four Components Of Every Acid Base Reaction<\/span><\/a><\/li>\n<li class=\"p1\"><a href=\"#two\"><span class=\"s1\"><span class=\"s1\">What Makes An Acid-Base Reaction Favorable? (Hint: It Has To Do With The Stability Of The Conjugate Base)<\/span><\/span><\/a><\/li>\n<li class=\"p1\"><a href=\"#three\">The Acidity Of A Molecule Is Directly Related To The Ability Of The Conjugate Base To Stabilize Negative Charge<\/a><\/li>\n<li class=\"p1\"><a href=\"#four\">Any Factor Which Stabilizes The Conjugate Base Will Lead To An Increase In Acidity<\/a><\/li>\n<li class=\"p1\"><a href=\"#five\">Acid-Base Reactions That Go From A Less Stable (i.e. More Basic) Anion To A More Stable (i.e. Less Basic) Anion Are Energetically Favorable<\/a><\/li>\n<li><a href=\"#notes\">Notes<\/a><\/li>\n<li><a href=\"#quizzes\">Quiz Yourself!<\/a><\/li>\n<\/ol>\n<hr \/>\n<h2><strong><a id=\"one\"><\/a>1. The Four Components Of Every Acid Base Reaction In Organic Chemistry<\/strong><\/h2>\n<p>In the first post I made <a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/09\/19\/introduction-to-acid-base-reactions\/\">introducing acid base reactions<\/a>, I just said that the first order of business is just to figure out the bonds that form and the bonds that break, and recognize the four components. \u00a0Like this.<\/p>\n<p><img decoding=\"async\" class=\"aligncenter wp-image-14124\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/1-an-acid-base-reaction-that-works-hf-plus-nanh2-giving-nh3-and-naf-form-and-break-h.gif\" alt=\"an-acid-base-reaction-that-works-hf-plus-nanh2-giving-nh3-and-naf-form-and-break-h\" width=\"630\" height=\"246\" \/><a href=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2012\/04\/acidbase11.png\"><br \/>\n<\/a>This is the pattern of an acid-base reaction in organic chemistry: we&#8217;re swapping a <strong>hydrogen<\/strong> between two atoms. Actually, since the hydrogen doesn&#8217;t take any electrons with it when this occurs, we&#8217;re technically swapping H+ (a <strong>proton<\/strong>). We have names for each of the species involved:<\/p>\n<ul>\n<li>The molecule which loses H+ \u00a0is called the <strong>acid\u00a0<\/strong><\/li>\n<li>The molecule which gains H+ is called the <strong>base<\/strong><\/li>\n<li>After gaining H+, the base becomes the <strong>conjugate acid<\/strong><\/li>\n<li>After losing H+, the acid becomes the <strong>conjugate base.<\/strong><\/li>\n<\/ul>\n<h2><a id=\"two\"><\/a>2. What Makes An Acid-Base Reaction Favorable? (Hint: It Has To Do With The Stability Of The Conjugate Base)<\/h2>\n<p>Although this helps us recognize the pattern, it doesn&#8217;t really help us answer &#8220;why?&#8221;. For instance, why does the above reaction proceed well, but the reaction below does not? After all, it&#8217;s also technically an acid-base reaction.<\/p>\n<p><img decoding=\"async\" class=\"aligncenter wp-image-14125\" title=\" \" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/2-acid-base-reaction-that-does-not-proceed-is-nh3-plus-naf-giving-hf-and-nanh2.gif\" alt=\"acid-base-reaction-that-does-not-proceed-is-nh3-plus-naf-giving-hf-and-nanh2\" width=\"630\" height=\"107\" \/><\/p>\n<p>Now we can circle back and start addressing this important question.<\/p>\n<p>Let&#8217;s start with some simple examples. Here are four sample acid-base reactions. If you read about the stability of negative charge earlier, you should be able to gauge which of these will be <strong>more favorable<\/strong> and which are <strong>less favorable<\/strong>. (Feel free to ignore the backwards arrow for now)<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14126\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/3-four-sample-acid-base-reactions-hf-h2o-h2o-to-h3o-nh3-to-nh2-and-ch4-to-ch3.gif\" alt=\"four-sample-acid-base-reactions-hf-h2o-h2o-to-h3o-nh3-to-nh2-and-ch4-to-ch3\" width=\"580\" height=\"322\" \/><\/p>\n<h2><a id=\"three\"><\/a>3. The Acidity Of A Molecule Is Directly Related To The Ability Of The Conjugate Base To Stabilize Negative Charge<\/h2>\n<p>Let&#8217;s look at this and think about it:<\/p>\n<ul>\n<li>In each reaction, the molecule on the far left is the acid, which is donating a proton to water (the base), forming H<sub>3<\/sub>O(+) [the <strong>conjugate acid<\/strong>] and an anion (the <strong>conjugate base<\/strong>).<\/li>\n<li>Notice how the charges change: in each case, the conjugate base is more negative than the acid, and the conjugate acid is more positive than the base.<strong>This is always true for acid-base reactions.\u00a0<\/strong><\/li>\n<li>Since every reaction here involves H<sub>2<\/sub>O and H<sub>3<\/sub>O(+), the <strong>only difference<\/strong> between each reaction is the identity of the <strong>acid<\/strong> and the <strong>conjugate base.<\/strong><\/li>\n<li>All else being equal, a <strong>neutral<\/strong> molecule is <strong>more stable<\/strong> than its conjugate base (nature seeks to minimize charges). The differences in stability between the neutral molecules (on the left) is trivial compared to the difference in stability between the charged molecules (on the right).<\/li>\n<li>\u00a0Therefore,<strong> understanding the factors that stabilize negative charge<\/strong> is going to be <strong>key<\/strong>\u00a0to understanding which of these are most favorable and which are least favorable.<\/li>\n<\/ul>\n<p>If you think back to the <strong>factors that stabilized negative charge<\/strong>, as we went from left to right across the periodic table we got this trend:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14127\" title=\" \" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/4-stability-of-negative-charge-increases-going-from-left-to-right-along-periodic-table-ch3-is-least-stable-f-is-most-stable.gif\" alt=\"stability-of-negative-charge-increases-going-from-left-to-right-along-periodic-table-ch3-is-least-stable-f-is-most-stable\" width=\"600\" height=\"185\" \/>Of these four species, fluoride ion (F-) is the <strong>most<\/strong> stable.<\/p>\n<p>Therefore, of all the four species listed in the reactions above, we should expect<strong> H-F<\/strong> to be the <strong>most<\/strong> likely to give up its proton to form its conjugate base, F(-). In other words, <strong>H-F is the most acidic <\/strong>because its conjugate base is<strong> best able<\/strong> to <strong>stabilize negative charge<\/strong>.<\/p>\n<p>Of these four species, CH<sub>3<\/sub>(-) is the <strong>least<\/strong> stable.<\/p>\n<p>Therefore of all the four species listed we should expect <strong>H-CH<sub>3<\/sub><\/strong> to be the <strong>least<\/strong> likely to give up its proton to form its conjugate base, CH<sub>3<\/sub>(-). In other words, <strong>H-CH<sub>3<\/sub> is the least acidic.\u00a0<\/strong><\/p>\n<h2><a id=\"four\"><\/a>4. Any Factor Which Stabilizes The Conjugate Base Will Lead To An Increase In Acidity<\/h2>\n<p>Let&#8217;s repeat this, in different form.<\/p>\n<ul>\n<li>The acidity of a species is directly related to the\u00a0<strong>stability\u00a0<\/strong>of its conjugate base.<\/li>\n<\/ul>\n<p>Therefore any factor which\u00a0<strong>stabilizes\u00a0<\/strong>the conjugate base (<em>specifically, the <strong>electron pair<\/strong> of the conjugate base)<\/em> will result in an <strong>increase\u00a0<\/strong>in acidity.<\/p>\n<p>What are some of the factors which stabilize negative charge and would therefore lead to an increase in acidity? There are seven: charge, electronegativity, polarizability, resonance, inductive effects, orbitals, and aromaticity. (<span style=\"color: #993366;\"><em>See article &#8211; <a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2012\/02\/27\/7-factors-that-stabilize-negative-charge-in-organic-chemistry\/\">Seven Factors Which Stabilize Negative Charge in Organic Chemistry<\/a><\/em><\/span>)<\/p>\n<p><strong>Every trend that leads to a stabilization of negative charge is going to have a direct impact on acidity. <\/strong>More specifically, stabilizing negative charge will make the conjugate acid more acidic.<\/p>\n<h2><a id=\"five\"><\/a>5. Acid-Base Reactions That Go From A Less Stable (i.e. More Basic) Anion To A More Stable (i.e. Less Basic) Anion Are Energetically Favorable<\/h2>\n<p>So for the reaction at the very top, we&#8217;re going from a <strong>less stable <\/strong>anion (H<sub>2<\/sub>N<sup>\u2013<\/sup>) to a <strong>more stable anion <\/strong>(F<sup>&#8211;<\/sup>). This is <strong>energetically favorable, <\/strong>like water flowing downhill.\u00a0So this reaction proceeds.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14128\" title=\" \" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/5-predicting-acid-base-reactions-is-about-knowing-which-anions-are-more-stable-and-less-stable.gif\" alt=\"predicting-acid-base-reactions-is-about-knowing-which-anions-are-more-stable-and-less-stable\" width=\"600\" height=\"232\" \/><\/p>\n<p>The reverse reaction would involve going from a <strong>more stable anion <\/strong>(F<sup>&#8211;<\/sup>) to a <strong>less stable anion <\/strong>(H<sub>2<\/sub>N<sup>&#8211;<\/sup>). This is <strong>energetically unfavorable<\/strong>, and does not proceed satisfactorily.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14129\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/6-rule-for-acid-base-reactions-is-stronger-acid-plus-stronger-base-gives-weaker-acid-and-weaker-base.gif\" alt=\"rule-for-acid-base-reactions-is-stronger-acid-plus-stronger-base-gives-weaker-acid-and-weaker-base\" width=\"600\" height=\"188\" \/><\/p>\n<p>Of course this is still pretty vague at the moment &#8211; we can actually be a lot more exact about this, as we&#8217;ll see. In the next post, though, we&#8217;ll look at these exact same reactions from a slightly different angle.<\/p>\n<p><strong>Next Post:\u00a0<a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/04\/16\/walkthrough-of-acid-base-reactions-2-basicity\/\"> The Stronger The Acid, The Weaker The Conjugate Base<\/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\/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\/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\/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\/2010\/09\/29\/how-to-use-a-pka-table\/\" class=\"\"><span>How to Use a pKa Table<\/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\/3444-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 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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\/3452-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\/3453-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\/3454-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","protected":false},"excerpt":{"rendered":"<p>An Introduction to Acid Base Reactions In Organic Chemistry Now that we&#8217;ve described how to figure out where the electrons are in a molecule, \u00a0the <\/p>\n","protected":false},"author":1,"featured_media":37419,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1407],"tags":[163,164,811,176,177,812,591,586,389,388,514],"post_folder":[],"class_list":["post-4934","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-acid-base-reactions","tag-acidity","tag-acids","tag-anion","tag-bases","tag-basicity","tag-cation","tag-charge","tag-conjugate-base","tag-negative-charge","tag-positive-charge","tag-stability"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Acid Base Reactions In Organic Chemistry &#8211; Master Organic Chemistry<\/title>\n<meta name=\"description\" content=\"The four components of acid base reactions in organic chemistry, and the relationship between acidity &amp; ability of the 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