{"id":8907,"date":"2015-05-06T16:34:54","date_gmt":"2015-05-06T21:34:54","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=8907"},"modified":"2026-04-11T05:50:06","modified_gmt":"2026-04-11T10:50:06","slug":"alcohol-oxidation-strong-and-weak-oxidants","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2015\/05\/06\/alcohol-oxidation-strong-and-weak-oxidants\/","title":{"rendered":"Alcohol Oxidation: &#8220;Strong&#8221; and &#8220;Weak&#8221; Oxidants"},"content":{"rendered":"<p><strong>Simplifying Alcohol Oxidation: &#8220;Strong&#8221; Oxidants and &#8220;Weak&#8221;\u00a0 \u00a0Oxidants<\/strong><\/p>\n<p>Here&#8217;s what we&#8217;ll talk about today: reagents for the oxidation of alcohols.<\/p>\n<p>For the purposes of introductory organic chemistry,\u00a0 it&#8217;s helpful to break oxidants for alcohols into two categories: &#8220;<strong>weak<\/strong>&#8221; and &#8220;<strong>strong<\/strong>&#8220;.<\/p>\n<ul>\n<li>&#8220;<strong>Weak<\/strong>&#8221; oxidants such as pyridinium chlorochromate (PCC), Dess-Martin Periodinane (DMP), and the Swern will only oxidize <strong>primary alcohols<\/strong> to <strong>aldehydes<\/strong>.<\/li>\n<li>&#8220;<strong>Strong<\/strong>&#8221; oxidants such as chromic acid (H<sub>2<\/sub>CrO<sub>4<\/sub>) and KMnO<sub>4<\/sub> will oxidize\u00a0 <strong>primary alcohols<\/strong> to <strong>carboxylic acids<\/strong>.<\/li>\n<\/ul>\n<p><span style=\"color: #800080;\"><em>Note &#8211; the distinction between &#8220;strong&#8221; and &#8220;weak&#8221; oxidants is not really a thing, as far as organic chemistry is concerned. It&#8217;s more like a helpful mental category for introductory organic chemistry students to help you to remember that some oxidants will convert primary alcohols to aldehydes and others to carboxylic acids.\u00a0<\/em><\/span><\/p>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-15232\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/0-oxidation-of-alcohols-break-summary-strong-and-weak-oxidants-chromic-acid-h2cro4.gif\" alt=\"oxidation of alcohols break summary strong and weak oxidants chromic acid h2cro4\" width=\"600\" height=\"435\" \/><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">An Oxidation Reaction Forms C-O and Breaks C-H On The Same\u00a0 Carbon<\/a><\/li>\n<li><a href=\"#two\">Another Oxidation: Secondary\u00a0 Alcohols To Ketones<\/a><\/li>\n<li><a href=\"#three\">Oxidation\u00a0 of Primary\u00a0 Alcohols To Carboxylic Acids<\/a><\/li>\n<li><a href=\"#four\">Tertiary\u00a0 Alcohols Do Not Undergo Oxidation<\/a><\/li>\n<li><a href=\"#five\">Climbing The Oxidation Ladder, One or Two Rungs At A Time<\/a><\/li>\n<li><a href=\"#six\">&#8220;Weak&#8221; Oxidants Oxidize Primary Alcohols To Aldehydes &#8211; And Stop There<\/a><\/li>\n<li><a href=\"#seven\">&#8220;Strong&#8221; Oxidants Oxidize Primary Alcohols\u00a0 To Carboxylic Acids<\/a><\/li>\n<li><a href=\"#eight\">Summary: &#8220;Strong&#8221; and &#8220;Weak&#8221; Oxidants for Alcohol Oxidation<\/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<hr \/>\n<h2><a id=\"one\"><\/a>1. An Oxidation Reaction Forms C\u2013O and Breaks C\u2013H On the Same Carbon<\/h2>\n<p>Here we are, at least \u00a0fifteen articles into this series on alcohols, and all we\u2019ve really talked about is substitution and elimination reactions, with a little bit of acid-base chemistry mixed in.<\/p>\n<p>We haven\u2019t even scratched the surface of one of the most important classes of reaction for alcohols &#8211; one that becomes crucial as you move into Org 2.<\/p>\n<p>I\u2019m talking about <strong>oxidation reactions<\/strong>.<\/p>\n<p>What do I mean by an &#8220;oxidation reaction&#8221;, anyway?<\/p>\n<p>Let&#8217;s start by examining the bonds that form and the bonds that break in this process, where we convert a primary alcohol to an aldehyde:<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-15225\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-transformation-of-primary-alcohol-to-aldehyde-using-a-weak-oxidant-no-over-oxidation.gif\" alt=\"transformation of primary alcohol to aldehyde using a weak oxidant no over oxidation\" width=\"630\" height=\"170\" \/><\/p>\n<p>No, &#8220;Eye of newt&#8221; doesn&#8217;t actually do oxidation reactions; a specific example of an oxidant here could be PCC, DMP, or Swern oxidation. The point here is not to focus on the specific reagent but to pay attention to the bonds that form and break in this reaction.<\/p>\n<p>The key process here is that we&#8217;re <strong>forming a C-O bond and breaking a C-H bond\u00a0<\/strong>on the same carbon.\u00a0<strong>That&#8217;s a sure sign of an oxidation reaction<\/strong>. For more background on oxidation reactions in organic chemistry, check out this<a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/08\/01\/oxidation-and-reduction-in-organic-chemistry\/\"> previous post<\/a><span style=\"color: #993366;\"> [\u00a0<em>\u00a0Quick summary: compare oxidation states in carbon to those in transition metals. Essentially we&#8217;re trading a bond between carbon and an atom less electronegative than carbon (H) for one more electronegative than carbon (O). If you think back to Gen Chem and transition metal oxidation states, this would correspond to an increase in oxidation state<\/em>].<\/span><\/p>\n<h2><a id=\"two\"><\/a>2. Another Oxidation: Secondary Alcohols To Ketones<\/h2>\n<p>Here&#8217;s another example for you. Starting with a secondary alcohol, we throw in some &#8220;wing of bat&#8221;, and voila! \u00a0We end up with a ketone!<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-15226\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-oxidation-of-secondary-alcohol-to-ketone-using-strong-or-weak-oxidant-oxidation-break-ch-form-co-on-same-carbon.gif\" alt=\"oxidation of secondary alcohol to ketone using strong or weak oxidant oxidation break ch form co on same carbon\" width=\"630\" height=\"225\" \/><\/p>\n<p>&nbsp;<\/p>\n<p>Again, we&#8217;re breaking C-H and forming C-O here. By the way, that [O] is shorthand you&#8217;ll see occasionally: it just means, &#8220;oxidation&#8221;.<\/p>\n<h2><a id=\"three\"><\/a>3.\u00a0 Oxidation of Primary Alcohols To Carboxylic Acids<\/h2>\n<p>Now let&#8217;s look at this third reaction, where we break out some very precious &#8220;powdered unicorn horn&#8221;.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15227\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-oxidation-of-primary-alcohols-to-carboxylic-acids-using-strong-oxidant.gif\" alt=\"oxidation of primary alcohols to carboxylic acids using strong oxidant\" width=\"630\" height=\"204\" \/><\/p>\n<p>That powdered \u00a0unicorn horn is powerful stuff! When we count the bonds formed and broken, notice that we formed\u00a0<strong>two\u00a0<\/strong>new C-O bonds and broke\u00a0<strong>two\u00a0<\/strong>C-H bonds. In other words, using this one reagent resulted in<strong> two oxidations\u00a0at the same carbon!<\/strong><\/p>\n<p>Note, however, that our magic unicorn horn only performs one oxidation on secondary alcohols, giving us a ketone (just like, the previously described &#8220;wing of bat&#8221;)<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15228\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/4-oxidation-of-secondary-alcohol-to-ketone-with-strong-oxidant-ends-up-at-ketone-stage.gif\" alt=\"oxidation of secondary alcohol to ketone with strong oxidant ends up at ketone stage\" width=\"630\" height=\"181\" \/><\/p>\n<h2><a id=\"four\"><\/a>4. Tertiary Alcohols Do Not Undergo Oxidation<\/h2>\n<p>Finally, just so tertiary alcohols aren&#8217;t left out, let&#8217;s see what happens when they&#8217;re treated with any one of our magical reagents.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15229\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/5-no-matter-what-the-oxidant-tertiary-alcohols-are-not-oxidized-with-either-strong-or-weak-oxidants.gif\" alt=\"no matter what the oxidant tertiary alcohols are not oxidized with either strong or weak oxidants\" width=\"600\" height=\"244\" \/><\/p>\n<p>Nothing! Eye of newt, wing of bat, powdered unicorn horn &#8211; no matter how powerful, none of them are able to oxidize our tertiary alcohol.<\/p>\n<p>Why is that? \u00a0If you look closely, there&#8217;s no C-H on the carbon of the tertiary alcohol and no oxidation occurs. We would have to break a C-C bond in order for an oxidation to occur, and none of these reagents are competent to do this [for a clue as to why, see the next post]<\/p>\n<p><span style=\"color: #993366;\">[<em>BTW: that carbon of an alcohol attached directly to C-OH is sometimes called the &#8220;carbinol&#8221; carbon<\/em>]<\/span><\/p>\n<h2><a id=\"five\"><\/a>5. Climbing The Oxidation Ladder, One Or Two Rungs At A Time<\/h2>\n<p>Let&#8217;s organize all of these reactions into a table. In one of the most powerful\u00a0analogies in organic chemistry, imagine we have a &#8220;ladder&#8221; of oxidation states for carbon. Alcohol is at the bottom of our miniature ladder here, and each oxidation goes a step up [we say &#8220;oxidize\u00a0up&#8221; because we&#8217;re increasing the oxidation state, i.e. making it more positive].<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15230\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/6-simple-oxidation-ladder-showing-increase-in-oxidation-state-going-from-primary-alcohol-to-aldehyde-to-carboxylic-acid-and-secondary-alcohol-to-ketone-but-no-transition-to-ester.gif\" alt=\"simple oxidation ladder showing increase in oxidation state going from primary alcohol to aldehyde to carboxylic acid and secondary alcohol to ketone but no transition to ester\" width=\"630\" height=\"489\" \/><\/p>\n<p><strong>One<\/strong> step &#8220;up&#8221; from a <strong>primary alcohol<\/strong> is an <strong>aldehyde<\/strong>, which we showed in example 1.<\/p>\n<p><strong>Two<\/strong> steps &#8220;up&#8221; from a<strong> primary alcohol<\/strong> [and one step up from an aldehyde] is a<strong> carboxylic acid<\/strong>, which we showed in example 3.<\/p>\n<p><strong>One<\/strong> step &#8220;up&#8221; from a <strong>secondary alcohol<\/strong> is a <strong>ketone<\/strong>, which we showed in example 2 and also with a &#8220;stronger&#8221; oxidant in example 3.<\/p>\n<p>And in example 4 we showed that oxidation &#8220;up&#8221; from a tertiary alcohol isn&#8217;t possible even with the help of these &#8220;magical&#8221; reagents we&#8217;ve been using.<\/p>\n<p>By the way, shouldn&#8217;t there also be a step &#8220;up&#8221; from a ketone? Yes &#8211; it would be an ester [shown in grey]. But none of the reagents we&#8217;ll talk about here are capable of climbing this rung of the ladder [again, it would involve breaking a C-C bond]. \u00a0Later on, you might learn about a special way to do it [<em>See post: <a href=\"https:\/\/www.masterorganicchemistry.com\/2018\/10\/08\/nitration-baeyer-villiger\/\">Baeyer-Villiger Reaction<\/a><\/em>] which we&#8217;ll discuss when we go through reactions of ketones.<\/p>\n<h2><a id=\"six\"><\/a>6. &#8220;Weak&#8221; Oxidants Oxidize Primary Alcohols To Aldehydes, and Stop There<\/h2>\n<p>Now we&#8217;re going to stop being so silly and get to specific reagents instead of talking about &#8220;eye of newt&#8221;, &#8220;wing of bat&#8221;, and &#8220;powdered unicorn horn&#8221;.<\/p>\n<p>But first, here&#8217;s a useful distinction to\u00a0make in keeping track of oxidizing agents.<\/p>\n<p><strong>&#8220;Weak&#8221; Oxidants<\/strong><\/p>\n<p>Some oxidants will react with primary alcohols to give aldehydes, and stop there.\u00a0<strong>Let&#8217;s call these &#8220;weak&#8221; oxidants.\u00a0<\/strong><\/p>\n<p>They don&#8217;t go on to the next &#8220;rung&#8221; up i.e. carboxylic acids.<\/p>\n<p>It&#8217;s a bit of an oversimplification [<a href=\"#noteone\">Note 1<\/a>] but it will do for our purposes.<\/p>\n<p>Examples of this are <a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/09\/09\/reagent-friday-pcc-pyridinium-chlorochromate\/\">pyridinium chlorochromate <\/a>(PCC), <a href=\"http:\/\/en.wikipedia.org\/wiki\/Dess\u2013Martin_periodinane\" target=\"_blank\" rel=\"noopener noreferrer\">Dess-Martin Periodinane<\/a> (DMP), the <a href=\"http:\/\/en.wikipedia.org\/wiki\/Swern_oxidation\" target=\"_blank\" rel=\"noopener noreferrer\">Swern oxidation<\/a> [(COCl)<sub>2<\/sub>, DMSO, NEt<sub>3<\/sub>)] and CrO<sub>3<\/sub>\/pyridine (the &#8220;<a href=\"http:\/\/en.wikipedia.org\/wiki\/Collins_reagent\" target=\"_blank\" rel=\"noopener noreferrer\">Collins reagent<\/a>&#8220;) all shown below. There are many, many more oxidants that will do this transformation than those I just mentioned; these are merely the reagents encountered most often in undergraduate courses.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15233\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/7-various-reagents-for-oxidation-of-primary-alcohols-to-aldehydes-that-will-also-oxidize-secondary-alcohols-to-ketones-include-pcc-.gif\" alt=\"various reagents for oxidation of primary alcohols to aldehydes that will also oxidize secondary alcohols to ketones include pcc\" width=\"600\" height=\"419\" \/><\/p>\n<p>As mentioned,<strong> these oxidizing agents will also convert secondary alcohols to ketones.<\/strong><\/p>\n<h2><strong><a id=\"seven\"><\/a>7. &#8220;Strong&#8221; Oxidants Oxidize Primary\u00a0 Alcohols\u00a0 To Carboxylic Acids<\/strong><\/h2>\n<p>A second class of oxidants are more vigorous. They will convert primary alcohols to carboxylic acids [two steps &#8220;up&#8221;] in one flask.<\/p>\n<p>Let&#8217;s call these\u00a0<strong>strong oxidants.<\/strong> They fall into two general categories: potassium permanganate \u00a0(KMnO<sub>4<\/sub>) and Cr(VI) species, which are essentially different precursors of\u00a0chromic acid (H<sub>2<\/sub>CrO<sub>4<\/sub>).<\/p>\n<p>[I&#8217;ve written before that H<sub>2<\/sub>CrO<sub>4<\/sub> \u00a0is one of the most annoying reagents in organic chemistry, because it has so many potential precursors spread throughout different textbooks. K<sub>2<\/sub>Cr<sub>2<\/sub>O<sub>7<\/sub>, Na<sub>2<\/sub>Cr<sub>2<\/sub>O<sub>7<\/sub>, Na<sub>2<\/sub>CrO<sub>4<\/sub>, K<sub>2<\/sub>CrO<sub>4<\/sub>, CrO<sub>3<\/sub>\/H<sub>3<\/sub>O+, Jones reagent &#8211; <strong><a href=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2015\/05\/h2cro4.png\">they&#8217;re all essentially the same thing<\/a><\/strong>, at least for our purposes. ]<\/p>\n<p>They will also oxidize secondary alcohols to ketones (and stop there).<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15231\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/8-strong-oxidants-convert-primary-alcohols-to-carboxylic-acids-include-kmno4-h2cro4-chromic-acid-potassium-permanganate.gif\" alt=\"strong oxidants convert primary alcohols to carboxylic acids include kmno4 h2cro4 chromic acid potassium permanganate\" width=\"600\" height=\"451\" \/><\/p>\n<p>And like I said earlier, neither strong nor weak oxidants will oxidize tertiary alcohols.<\/p>\n<h2><a id=\"eight\"><\/a>8. Summary: Strong and\u00a0 Weak Oxidants for Alcohol Oxidation<\/h2>\n<p>Let&#8217;s make a table, shall we? This is the &#8220;bottom line&#8221; for this post.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15234\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/9-summary-to-get-aldehyde-from-primary-alcohol-use-weak-oxidant-pcc-dmp-swern-.gif\" alt=\"summary to get aldehyde from primary alcohol use weak oxidant pcc dmp swern\" width=\"600\" height=\"427\" \/><\/p>\n<ul>\n<li><strong>&#8220;Weak&#8221; oxidants convert primary alcohols to aldehydes and stop there.<\/strong> They also oxidize secondary alcohols to ketones.<\/li>\n<li><strong>&#8220;Strong&#8221; oxidants convert primary alcohols to carboxylic acids.<\/strong> They also oxidize secondary alcohols to ketones.<\/li>\n<li><strong>None of the reagents we&#8217;ve encountered will oxidize tertiary alcohols.<\/strong><\/li>\n<\/ul>\n<h2>Next time &#8211; How Oxidation Reactions Work<\/h2>\n<p>So how do these mysterious reagents work, anyway?<\/p>\n<p>Reagents for oxidation of alcohols was one of those things that <strong>made me feel really dumb<\/strong> when I learned organic chemistry.<\/p>\n<p><strong>\u00a0The reagents that were given to us might have well been &#8220;eye of newt&#8221; and &#8220;powdered unicorn horn&#8221; since they were introduced without any background\u00a0or context and disappeared just as quickly after the section on oxidation was over.<\/strong><\/p>\n<p>It was only later that I understood that oxidation is not nearly as complicated as these weird reagents make it \u00a0seem. In fact, the underlying process is in most cases extremely familiar &#8211; it&#8217;s just not taught that way!<\/p>\n<p>In the next post, we&#8217;ll discuss the common &#8211; and very familiar! &#8211; mechanistic step that (almost) all oxidation reactions you&#8217;ll learn have in common. Not only will oxidation reactions then become less mysterious.<\/p>\n<p><strong>Next Post &#8211; <a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/05\/21\/demystifying-alcohol-oxidations\/\">Demystifying The Mechanisms of Alcohol Oxidations<\/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\/05\/21\/demystifying-alcohol-oxidations\/\" class=\"\"><span>Demystifying The Mechanisms of Alcohol Oxidations<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/06\/03\/reagent-friday-chromic-acid-h2cro4\/\" class=\"\"><span>Reagent Friday: Chromic Acid, H2CrO4<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/08\/01\/oxidation-and-reduction-in-organic-chemistry\/\" class=\"\"><span>Oxidation and Reduction in Organic Chemistry<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/08\/08\/oxidation-ladders\/\" class=\"\"><span>Oxidation Ladders<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/reaction-guide\/oxidation-of-primary-alcohols-to-aldehydes\/\" class=\"\"><span>Oxidation of Primary Alcohols to Aldehydes using PCC (MOC Membership))<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/reaction-guide\/oxidation-of-primary-alcohols-to-carboxylic-acids\/\" class=\"\"><span>Oxidation of primary alcohols to carboxylic acids (MOC Membership)<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/09\/09\/reagent-friday-pcc-pyridinium-chlorochromate\/\" class=\"\"><span>Reagent Friday: PCC (Pyridinium Chlorochromate)<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/reaction-guide\/swern-oxidation-of-alcohols-to-aldehydes-and-ketones\/\" class=\"\"><span>Swern Oxidation of Alcohols To Aldehydes and Ketones<\/span><\/a><\/li><\/ul><\/div>\n<p><strong><a id=\"noteone\"><\/a>Note 1. <\/strong>It&#8217;s an oversimplification because the first step in oxidation of an aldehyde is generally addition of water to form a hydrate, which is then oxidized to the carboxylic acid. Some oxidants we call &#8220;weak&#8221; (e.g. CrO<sub>3<\/sub>, pyridine) can thus be &#8220;strong&#8221; if water is present. It&#8217;s a teaching kludge, but good enough for our purposes, for now.<\/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\/3637-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\/3638-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\/3634-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\/3635-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\/3636-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\/1600-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\/1599-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\/1531-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\/1526-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become 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id=\"references\"><\/a>(Advanced) References and Further Reading<\/h2>\n<p>Oxidation of secondary alcohols (\u2018weak\u2019 oxidation):<\/p>\n<ol>\n<li><strong>Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones<br \/>\n<\/strong>D. B. Dess and J. C. Martin<strong><br \/>\n<\/strong><em>The Journal of Organic Chemistry<\/em><strong> 1983, <\/strong><em>48<\/em> (22), 4155-4156<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/jo00170a070\">10.1021\/jo00170a070<\/a><\/li>\n<li><strong>A useful 12-I-5 triacetoxyperiodinane (the Dess-Martin periodinane) for the selective oxidation of primary or secondary alcohols and a variety of related 12-I-5 species<br \/>\n<\/strong>Daniel B. Dess and J. C. Martin<strong><br \/>\n<\/strong><em>Journal of the American Chemical Society<\/em><strong> 1991, <\/strong><em>113<\/em> (19), 7277-7287<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/ja00019a027\">1021\/ja00019a027<\/a><br \/>\nThese two articles are on the development and use of the compound now known as \u201cDess-Martin periodinane\u201d, a hypervalent I(V) compound that has found widespread use as a mild oxidant in organic synthesis. Prof. J. C. Martin spent most of his career at University of Illinois Urbana-Champaign and ended his career at Vanderbilt University. During his career he contributed a lot towards our understanding of hypervalent main-group chemistry, preparing many S(IV), S(VI), Br(III), I(III), I(V), and I(VII) compounds, among others.<\/li>\n<li><strong>Oxidation of alcohols by &#8220;activated&#8221; dimethyl sulfoxide. A preparative, steric and mechanistic study<br \/>\n<\/strong>Omura, K.; Swern, D.<strong><br \/>\n<\/strong><em>Tetrahedron<\/em><strong> 1978, <\/strong><em>34<\/em> (11): 1651\u20131660<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/www.sciencedirect.com\/science\/article\/abs\/pii\/0040402078801975\">1016\/0040-4020(78)80197-5<\/a><\/li>\n<li><strong>Structure of the dimethyl sulfoxide-oxalyl chloride reaction product. Oxidation of heteroaromatic and diverse alcohols to carbonyl compounds<br \/>\n<\/strong>Mancuso, A. J.; Brownfain, D. S.; Swern, D.<strong><br \/>\n<\/strong><em> Org. Chem.<\/em><strong> 1979, <\/strong><em>44<\/em> (23): 4148\u20134150<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/jo01337a028\">10.1021\/jo01337a028<\/a><\/li>\n<li><strong>Oxidation of long-chain and related alcohols to carbonyls by dimethyl sulfoxide &#8220;activated&#8221; by oxalyl chloride<br \/>\n<\/strong>Mancuso, A. J.; Huang, S.-L.; Swern, D.<strong><br \/>\n<\/strong><em>J. Org. Chem.<\/em><strong> 1978, <\/strong><em>43<\/em> (12): 2480\u20132482<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/jo00406a041\">10.1021\/jo00406a041<\/a><\/li>\n<li><strong>Mechanisms of dimethylsulfoxide oxidations<br \/>\n<\/strong>Kurt Torssell<br \/>\n<em>Tetrahedron Letters <\/em><strong>1966<\/strong> <em>7 <\/em>(37), 4445-4451<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/www.sciencedirect.com\/science\/article\/pii\/S0040403900700578\">1016\/S0040-4039(00)70057-8<\/a><br \/>\nThese papers are on what is now commonly called the \u201cSwern oxidation\u201d after its developer, Daniel Swern. This method is rather mild and uses DMSO, a common solvent, as the oxidant. However, this also results in the formation of dimethyl sulfide (which is notoriously stinky) as the product of the reaction, one of its noteworthy characteristics.<\/li>\n<li><strong>SYNTHESIS OF 1,1-DIMETHYLETHYL (S)-4-FORMYL-2,2-DIMETHYL-3-OXAZOLIDINECARBOXYLATE BY OXIDATION OF THE ALCOHOL<\/strong><br \/>\nAlessandro Dondoni and Daniela Perrone<br \/>\n<em>Org. Synth.<\/em> <strong>2000<\/strong>, <em>77<\/em>, 64<br \/>\n<strong>DOI<\/strong>:<a href=\"http:\/\/orgsyn.org\/demo.aspx?prep=V77P0064\"> 10.15227\/orgsyn.077.0064<\/a><br \/>\nThe final step (<strong>4<\/strong> -&gt; <strong>5<\/strong>) in this multistep procedure is a Swern oxidation. This is from <em>Organic Syntheses<\/em>, a source of reliable, independently tested synthetic organic procedures.<\/li>\n<li><strong>New and highly effective method for the oxidation of primary and secondary alcohols to carbonyl compounds<\/strong><br \/>\nE. J. Corey; C. U. Kim<br \/>\n<em>Journal of the American Chemical Society<\/em> <strong>1972<\/strong>, <em>94<\/em> (21): 7586\u20137587<br \/>\n<strong>DOI<\/strong>:<a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00776a056\">10.1021\/ja00776a056.<\/a><\/li>\n<li><strong>A method for the oxidation of sec,tert-1,2-diols to \u03b1-hydroxy ketones without carbon-carbon cleavage<\/strong><br \/>\nE. J. Corey; C. U. Kim<br \/>\n<em>Tetrahedron Letters<\/em> <strong>1974<\/strong>, <em>15<\/em> (3): 287\u2013290<br \/>\n<strong>DOI<\/strong>:<a href=\"https:\/\/www.sciencedirect.com\/science\/article\/pii\/S004040390182195X\">10.1016\/S0040-4039(01)82195-X<\/a><br \/>\nThese papers by Nobel Laureate Prof. E. J. Corey (Harvard) are on the development of what is now known as the \u201cCorey-Kim\u201d oxidation. This is very similar to the Swern oxidation in that DMSO is used as the oxidant, except that here NCS (N-chlorosuccinimide) is used instead of oxalyl chloride. The advantage with this procedure is that temperatures above \u201325 \u00b0C can be used, and the disadvantage is that substrates susceptible to chlorination by NCS cannot be used.<\/li>\n<li><strong> A New and Selective Oxidation of Alcohols<br \/>\n<\/strong>Pfitzner, K. E.; Moffatt, J. G.<strong><br \/>\n<\/strong><em>J. Am. Chem. Soc.<\/em><strong> 1963, <\/strong><em>85<\/em>: 3027<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00902a036\">10.1021\/ja00902a036<\/a><br \/>\nThis paper describes yet another DMSO-based oxidation, the Pfitzner-Moffatt oxidation, which is not used that much anymore due to the difficulties in separating out the dicyclohexylurea byproduct from the desired product.<\/li>\n<li><strong>EINE METHODE DER DEHYDRIERUNG VON SEKUNDAREN ALKOHOLEN ZU KETONEN. I, ZUR HERSTELLUNG VON STERINKETONEN UND SEXUALHORMONEN<br \/>\n<\/strong>R. V. Oppenauer<br \/>\n<em>Recl. Trav. Chim. Pays-Bas<\/em> <em>56<\/em> (2): 137\u2013144<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/recl.19370560206\">10.1002\/recl.19370560206<\/a><br \/>\nThis paper lays the basis for what is now called the Oppenauer oxidation, the oxidation of secondary alcohols to ketones using Al(i-PrO)<sub>3<\/sub> in excess acetone.<\/li>\n<li><strong>Oxidations with Manganese Dioxide<br \/>\n<\/strong>E. P. Papadopoulos, A. Jarrar, and C. H. Issidorides<br \/>\n<em>The Journal of Organic Chemistry<\/em><strong> 1966<\/strong>, <em>31<\/em> (2), 615-616<br \/>\n<strong>DOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/jo01340a520\">10.1021\/jo01340a520<\/a><br \/>\nAs this paper shows, MnO<sub>2<\/sub> can also be used for oxidation of secondary alcohols.Oxidation with PCC (pydinium chlorochromate):<\/li>\n<li><strong>Pyridinium chlorochromate. An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds<br \/>\n<\/strong>E. J. Corey, J. William Suggs<strong><br \/>\n<\/strong><em>Tetrahedron Letters <\/em>Volume 16, Issue 31, 1975, Pages 2647-2650<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/www.sciencedirect.com\/science\/article\/pii\/S004040390075204X\">10.1016\/S0040-4039(00)75204-X<\/a><br \/>\nThe original paper by Nobel Laureate Prof. E. J. Corey on the use of pyridinium chlorochromate as a mild oxidation reagent in organic synthesis.<\/li>\n<li>The story of the discovery of PCC was rather serendipitous, as explained by Prof. Suggs in this blog post:<br \/>\n<a href=\"https:\/\/blogs.sciencemag.org\/pipeline\/archives\/2005\/10\/11\/the_old_stuff#comment-2123\">Suggs<\/a><\/li>\n<li><strong>Pyridinium Chlorochromate: A Versatile Oxidant in Organic Synthesis<br \/>\n<\/strong> Piancatelli, A. Scettri, M. D&#8217;Auria<strong><br \/>\n<\/strong><em>Synthesis<\/em> <strong>1982<\/strong>; <em>1982<\/em>(4): 245-258<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/www.thieme-connect.com\/products\/ejournals\/abstract\/10.1055\/s-1982-29766\">10.1055\/s-1982-29766<\/a><br \/>\nReview on the applications of PCC in organic synthesis. Includes a discussion on the mechanism.<\/li>\n<li><strong>Kinetics and Mechanism of the Oxidation of Alcohols by Pyridinium Chlorochromate<br \/>\n<\/strong>Banerji Kalyan K.<strong><br \/>\n<\/strong><em> Chem. Soc. Jpn.<\/em> <strong>1978<\/strong>, <em>51<\/em> (9), 2732<br \/>\n<strong>DOI: <\/strong><a href=\"https:\/\/www.journal.csj.jp\/doi\/abs\/10.1246\/bcsj.51.2732\">10.1246\/bcsj.51.2732<\/a><br \/>\nA nice mechanistic study of PCC oxidation, and includes a probable mechanism of the reaction.<\/li>\n<li><strong>Stoichiometry of the oxidation of primary alcohols with pyridinium chlorochromate. Evidence for a two-electron change<br \/>\n<\/strong>Herbert C. Brown, C. Gundu Rao, and Surendra U. Kulkarni<strong><br \/>\n<\/strong><em>The Journal of Organic Chemistry<\/em> <strong>1979<\/strong> <em>44<\/em> (15), 2809-2810<br \/>\n<strong>DOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jo01329a051\">1021\/jo01329a051<\/a><strong><br \/>\n<\/strong>In this paper, Nobel Laureate H. C. Brown proves that PCC oxidations involve a transfer of 2 electrons from the Cr to the substrate. Therefore, one does not need to use an excess of PCC \u2013 1 equivalent works fine.<\/li>\n<li><strong>SYNTHESIS OF 1,2:4,5-DI-O-ISOPROPYLIDENE-D-erythro-2,3-HEXODIULO-2,6-PYRANOSE. A HIGHLY ENANTIOSELECTIVE KETONE CATALYST FOR EPOXIDATION<br \/>\n<\/strong>Yong Tu, Michael Frohn, Zhi-Xian Wang, and Yian Shi<strong><br \/>\n<\/strong><em>Org. Synth. <\/em><strong>2003<\/strong> <em>80<\/em>, 1<strong><br \/>\nDOI: <\/strong><a href=\"http:\/\/www.orgsyn.org\/demo.aspx?prep=v80p0001\">10.15227\/orgsyn.080.0001<\/a><br \/>\nThis tested procedure from <em>Organic Syntheses<\/em> uses PCC to make the chiral ketone catalyst for asymmetric epoxidation, known as \u2018Shi epoxidation\u2019 after its creator, Prof. Yian Shi (Colorado State).Oxidation of primary alcohols to carboxylic acids (\u2018strong\u2019 oxidation):<\/li>\n<li><strong>Synthesis of a model depsipeptide segment of Luzopeptins (BBM 928), potent antitumor and antiretroviral antibiotics<br \/>\n<\/strong>Marco A. Ciufolini and Shankar Swaminathan<br \/>\n<em>Tetrahedron Letters <\/em>Volume 30, Issue 23, <strong>1989<\/strong>, Pages 3027-3028<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/www.sciencedirect.com\/science\/article\/pii\/S0040403900993936\">1016\/S0040-4039(00)99393-6<\/a><br \/>\nStep <strong>f<\/strong> in the synthesis (<strong>Scheme 1<\/strong>) is an oxidation of a primary alcohol to carboxylic acid using KMnO<sub>4<\/sub>.<\/li>\n<li><strong>Stereocontrolled addition to a penaldic acid equivalent: an asymmetric of -\u03b2-hydroxy-L-glutamic acid<\/strong><br \/>\nPhilip Garner<strong><br \/>\n<\/strong><em>Tetrahedron Letters<\/em> Volume 25, Issue 51, <strong>1984<\/strong><em>, <\/em>5855-5858<strong><br \/>\nDOI<\/strong>:<a href=\"https:\/\/www.sciencedirect.com\/science\/article\/pii\/S0040403901817032\"> 10.1016\/S0040-4039(01)81703-2<\/a><br \/>\nThe final step (<strong>g<\/strong>, 6 -&gt; 7) in the synthesis in this paper is an oxidation of a primary alcohol to a carboxylic acid using KMnO<sub>4<\/sub>.The Jones oxidation, which uses chromic acid (CrO<sub>3<\/sub> in H<sub>2<\/sub>SO<sub>4<\/sub>) is a common method for the oxidation of primary alcohols to carboxylic acids. The drawback is of course the production of stoichiometric amounts of chromium waste.<\/li>\n<li><strong> Researches on acetylenic compounds. Part XIV. A study of the reactions of the readily available ethynyl-ethylenic alchohol, pent-2-en-4-yn-1-ol<br \/>\n<\/strong>Sir Ian Heilbron, E. R. H. Jones and F. Sondheimer<strong><br \/>\n<\/strong><em>J. Chem. Soc.,<\/em><strong> 1947, <\/strong>1586-1590<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.rsc.org\/en\/content\/articlelanding\/1947\/jr\/jr9470001586#!divAbstract\">10.1039\/JR9470001586<\/a><\/li>\n<li><strong>An Improved Procedure for the Oxidation of Alkynols to Alkynoic Acids<\/strong><br \/>\nB. C. Holland and N. W. Gilman<br \/>\n<em>Synth. Commun.<\/em> <strong>1974<\/strong>, <em>4<\/em>, 203-210<br \/>\n<strong>DOI:<\/strong><a href=\"https:\/\/www.tandfonline.com\/doi\/abs\/10.1080\/00397917408062073?tab=permissions&amp;scroll=top\"> 10.1080\/00397917408062073<\/a><\/li>\n<li><strong>Useful procedures for the oxidation of alcohols involving pyridinium dichromate in aprotic media<br \/>\n<\/strong>E. J. Corey, Greg Schmidt<strong><br \/>\n<\/strong><em>Tetrahedron Letters <\/em>Volume 20, Issue 5, <strong>1979<\/strong>, 399-402<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/www.sciencedirect.com\/science\/article\/pii\/S0040403901935154\">10.1016\/S0040-4039(01)93515-4<\/a><br \/>\nNobel Laureate Prof. E. J. Corey (Harvard) shows that PDC (pyridinium dichromate) in DMF can be used for the oxidation of primary alcohols to carboxylic acids.<\/li>\n<li><strong>Applications of the peracid-mediated oxidation of alcohols<br \/>\n<\/strong>James A. Cella, James P. McGrath, James A. Kelley, Omaya El Soukkary, and Lawrence Hilpert<strong><br \/>\n<\/strong><em>The Journal of Organic Chemistry<\/em><strong> 1977, <\/strong><em>42<\/em> (12), 2077-2080<strong><br \/>\nDOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/jo00432a008\">10.1021\/jo00432a008<\/a><strong><br \/>\n<\/strong>This paper demonstrates that a peracid (<em>m<\/em>CPBA) can directly oxidize secondary alcohols to esters, a tandem oxidation-Baeyer-Villiger reaction.<\/li>\n<\/ol>\n","protected":false},"excerpt":{"rendered":"<p>Simplifying Alcohol Oxidation: &#8220;Strong&#8221; Oxidants and &#8220;Weak&#8221;\u00a0 \u00a0Oxidants Here&#8217;s what we&#8217;ll talk about today: reagents for the oxidation of alcohols. For the purposes of introductory <\/p>\n","protected":false},"author":1,"featured_media":15232,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1420],"tags":[167,1065,919,1063,251,1066,291,1064],"post_folder":[],"class_list":["post-8907","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-alcohols-epoxides-ethers","tag-alcohols","tag-aldehyde","tag-carboxylic-acid","tag-dess-martin","tag-oxidation","tag-oxidation-ladder","tag-pcc","tag-swern"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Alcohol Oxidation: &quot;Strong&quot; &amp; &quot;Weak&quot; Oxidants - Master Organic Chemistry<\/title>\n<meta name=\"description\" content=\"Overview of alcohol oxidation: what bonds form and break, and the key difference between PCC, Swern, and DMP versus H2CrO4, CrO3\/H3O+ &amp; 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