{"id":7238,"date":"2013-04-23T09:40:13","date_gmt":"2013-04-23T13:40:13","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=7238"},"modified":"2026-04-18T06:31:04","modified_gmt":"2026-04-18T11:31:04","slug":"alkene-reactions-ozonolysis","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2013\/04\/23\/alkene-reactions-ozonolysis\/","title":{"rendered":"Alkene Reactions: Ozonolysis"},"content":{"rendered":"<p><strong>Ozonolysis of Alkenes and Alkynes\u00a0<\/strong><\/p>\n<ul>\n<li>Alkenes can undergo <strong>oxidative cleavage\u00a0<\/strong>with ozone (O<sub>3<\/sub>) to give carbonyl compounds, cleaving the C=C bond<\/li>\n<li>The reaction generates an\u00a0<strong>ozonide<\/strong> intermediate, which is then treated with a reducing agent (e.g. dimethyl sulfide or zinc) gives aldehydes or ketones depending on the structure of the starting alkene.<\/li>\n<li>Less commonly, the ozonide can be treated with an oxidizing agent such as hydrogen peroxide H<sub>2<\/sub>O<sub>2<\/sub> (&#8220;oxidative workup&#8221;) which will convert any aldehydes to carboxylic acids<\/li>\n<li>Cyclic alkenes are converted into linear products; molecules with multiple alkenes are converted into a mixture of fragments<\/li>\n<li>More electron-rich (i.e. more substituted) alkenes tend to react faster<\/li>\n<li>Alkynes can also undergo oxidative cleavage with O<sub>3<\/sub>, giving carboxylic acids. Alkynes are less reactive than alkenes towards O<sub>3<\/sub>.<\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-35281\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/08\/0-summary-of-ozonolysis-of-alkenes-with-reductive-or-oxidative-workup-ozonolysis-of-alkynes.gif\" alt=\"summary of ozonolysis of alkenes with reductive or oxidative workup ozonolysis of alkynes\" width=\"640\" height=\"535\" \/><\/a><\/p>\n<p><strong>Table Of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">Ozone (O<sub>3<\/sub>) Is A Powerful Oxidant For Cleaving Alkenes To Carbonyl Compounds<\/a><\/li>\n<li><a href=\"#two\">Ozonolysis With &#8220;Reductive Workup&#8221; :\u00a0 All C\u2013H Bonds Are Preserved<\/a><\/li>\n<li><a href=\"#three\">Oxidative Workup of Ozonolysis<\/a><\/li>\n<li><a href=\"#four\">Ozonolysis Of A Cyclic Alkenes Results In A Chain With Two Carbonyls<\/a><\/li>\n<li><a href=\"#five\">Ozonolysis Of A Compound With Multiple Alkenes Results In Fragments<\/a><\/li>\n<li><a href=\"#six\">Mechanism of Ozonolysis<\/a><\/li>\n<li><a href=\"#seven\">Oxidative Workup Mechanism<\/a><\/li>\n<li><a href=\"#eight\">Summary: Ozonolysis of Alkenes<\/a><\/li>\n<li><a href=\"#notes\">Notes<\/a><\/li>\n<li><a href=\"#quiz\">Quiz Yourself!<\/a><\/li>\n<li><a href=\"#furtherreading\">(Advanced) References and Further Reading<\/a><\/li>\n<\/ol>\n<hr \/>\n<h2><strong><a id=\"one\"><\/a>1. Ozone (O<sub>3<\/sub>) Is A Powerful Oxidant For Cleaving Alkenes To Carbonyl Compounds<\/strong><\/h2>\n<p>Ozone (O<sub>3<\/sub>) is a form of molecular oxygen containing\u00a0<em>three\u00a0<\/em>oxygen atoms, in contrast to the the more familiar dioxygen (O<sub>2<\/sub>) which we all know and breathe.\u00a0 [<span style=\"color: #993366;\"><em>O<sub>3<\/sub> and O<sub>2<\/sub> are <strong>allotropes<\/strong> of oxygen, just as diamond and graphite are allotropes of carbon<\/em><\/span>]. It has a distinctive sharp, almost metallic odor, detectible by the human nose in trace quantities, that will invoke memories of lightning storms and being near high-voltage power equipment.<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-35266\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/08\/1-structure-of-ozone-bond-lengths-and-angles-blue-color-reagent-in-organic-chemistry.gif\" alt=\"structure of ozone bond lengths and angles blue color reagent in organic chemistry\" width=\"640\" height=\"489\" \/><\/a><\/p>\n<p>Ozone is a much more aggressive oxidant than molecular oxygen. In organic chemistry, it is useful for oxidative cleavage of alkenes, a reaction that converts alkenes (and alkynes) to carbonyl compounds. It also has many commercial uses, such as disinfecting surfaces, rooms, and drinking water. Ozone can be conveniently generated on demand by passing a stream of O<sub>2<\/sub> through high voltage\u00a0 (<span style=\"color: #993366;\"><em>8000-15000 V, see this <a style=\"color: #993366;\" href=\"https:\/\/www.orgsyn.org\/demo.aspx?prep=CV3P0673\">freely accessible article from Org. Syn<\/a> for the original design<\/em><\/span>) ; household ozone generators are available for purchase on Amazon.<\/p>\n<p>Ozone forms naturally in the upper atmosphere through the interaction of O<sub>2<\/sub> with ultraviolet light, and serves to screen out damaging high-energy ultraviolet rays from hitting the earth&#8217;s surface (<span style=\"color: #993366;\"><em>UV light promotes the pi-pi* transition of an electron from the highest-occupied molecular orbital (HOMO) of ozone to the lowest unoccupied molecular orbital (LUMO) &#8211; s<\/em><em>ee<a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2016\/09\/16\/introduction-to-uv-vis-spectroscopy\/\"> UV spectroscopy<\/a> for more background on how this works<\/em><\/span>).<\/p>\n<p>Less usefully, O<sub>3<\/sub> forms in the lower atmosphere through interaction of oxygen with light, heat, and nitrogen oxides (<span style=\"color: #993366;\"><em>byproducts of gasoline combustion<\/em><\/span>) and is a component of smog. High levels of O<sub>3<\/sub> lead to rapid degradation of rubber and plastics and also cause respiratory problems.<\/p>\n<p>Ozone has two equivalent resonance forms. The resonance hybrid has an O-O bond length of 1.27 \u00c5, intermediate between O=O (1.21 \u00c5) and O-O (1.47 \u00c5) , and an interior bond angle of about 117\u00b0,\u00a0 pretty close to the 120\u00b0 bond angle of an ideal sp<sup>2\u00a0<\/sup>hybridization. [<a href=\"#noteone\"><span style=\"color: #ff0000;\">Note 1<\/span><\/a>]<\/p>\n<p>The hybridization of the terminal oxygen of ozone makes for a good quiz question:<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35259\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35259\"] {\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=\"35259\"] {\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=\"35259\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35259\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35259 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35259\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-n0ee9\" data-id=\"n0ee9\">\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\/2536-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\/2536-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<h2><strong><a id=\"two\"><\/a>2. Oxidative Cleavage of Alkenes With &#8220;Reductive Workup&#8221;<\/strong><\/h2>\n<p>When alkenes are treated with ozone, they undergo a reaction known as\u00a0<strong>ozonolysis <\/strong>(ozone,\u00a0 + <em>lysis<\/em> = breaking), a type of reaction known as <strong>oxidative cleavage<\/strong>.<\/p>\n<p>(<span style=\"color: #993366;\"><em>In organic chemistry, any reaction where a C-H or C-C bond is converted to a C-O bond is classified as an oxidation reaction &#8211; see <a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/08\/01\/oxidation-and-reduction-in-organic-chemistry\/\">Oxidations and Reductions in Organic Chemistry<\/a><\/em><\/span>).<\/p>\n<p>The C=C bond is broken and two new C=O bonds are formed. The resulting C=O groups are known as <strong>carbonyl\u00a0<\/strong>functional groups.<\/p>\n<p>Depending on the structure of the starting alkene, either aldehydes or ketones will be formed. If the alkenyl carbon has two hydrogens attached, formaldehyde (H<sub>2<\/sub>C=O) will be formed.<\/p>\n<p>In carrying out an ozonolysis reaction, O<sub>3<\/sub> is added to the alkene at low temperature until the alkene is completely consumed. The beautiful blue color of ozone serves as a convenient indicator &#8211; when the blue color persists, you know the reaction is done! [<a href=\"#notetwo\"><span style=\"color: #ff0000;\">Note 2<\/span><\/a>]<\/p>\n<p>Ozonolysis of an alkene results in an intermediate known as an <strong>ozonide<\/strong> (<span style=\"color: #993366;\"><em>more detail in the &#8220;Mechanism&#8221; section, below<\/em><\/span>).<\/p>\n<p>Like peroxides, ozonides are potentially explosive (the O-O bond is weak! ) and reasons of chemical safety, they should be broken down to carbonyl compounds through adding additional reagents, a procedure known as the <strong>workup<\/strong>. [<em><span style=\"color: #800080;\">The explosive nature of ozonides was first encountered in 1873 &#8211;\u00a0<\/span> <a href=\"#notethree\"><span style=\"color: #ff0000;\">Note 3<\/span> <\/a><\/em>]<\/p>\n<p>There are two different families of <strong>workups<\/strong> for ozonolysis reactions.<\/p>\n<p>The most common type of workup (&#8220;<strong>reductive workup<\/strong>&#8220;) involves adding a reducing agent to the ozonide, which accepts an oxygen atom and results in the formation of two new C=O groups.\u00a0 Typical reducing agents include dimethyl sulfide [<span style=\"color: #800080;\"><em>also known as (CH<sub>3<\/sub>)<sub>2<\/sub>S or DMS<\/em><\/span>), zinc with acid, or triphenylphosphine (PPh<sub>3<\/sub>). These safely break the O-O bond of the ozonide and leave all C-H bonds intact.<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-35267\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/08\/3-ozonolysis-of-alkenes-with-ozone-o3-results-in-aldehydes-and-ketones-reductive-workup.gif\" alt=\"ozonolysis of alkenes with ozone o3 results in aldehydes and ketones reductive workup\" width=\"640\" height=\"253\" \/><\/a><\/p>\n<p>Note the pattern of bonds formed and bonds broken in ozonolysis of alkenes with reductive workup: the C=C bond breaks and two new C=O bonds form.<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35260\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35260\"] {\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=\"35260\"] {\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=\"35260\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35260\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35260 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35260\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-9kle8\" data-id=\"9kle8\">\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\/2537-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\/2537-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>Depending on the structure of the starting alkene, either aldehydes or ketones will be formed. Reductive workup does not alter any additional bonds on the substrate.<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35261\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35261\"] {\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=\"35261\"] {\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=\"35261\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35261\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35261 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35261\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-jsp8u\" data-id=\"jsp8u\">\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\/2538-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\/2538-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>When\u00a0<strong>terminal\u00a0<\/strong>alkenes (i.e. alkenes that end in =CH<sub>2 <\/sub>) are treated with O<sub>3<\/sub> and subjected to reductive workup, formaldehyde will be formed.<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35262\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35262\"] {\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=\"35262\"] {\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=\"35262\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35262\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35262 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35262\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-4vvok\" data-id=\"4vvok\">\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\/2539-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\/2539-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<h2><a id=\"three\"><\/a>3. Oxidative Workup<\/h2>\n<p>A less common workup is known as &#8220;oxidative workup&#8221;. In this case, an oxidant such as hydrogen peroxide (H<sub>2<\/sub>O<sub>2<\/sub>) \u00a0is added to the ozonide. What happens is that any\u00a0<strong>aldehydes<\/strong> that form will be oxidized to give <strong>carboxylic acids<\/strong>.<\/p>\n<p>That is, in addition to the C=C bond breaking and two new C=O bonds forming, any <strong>C-H<\/strong> bonds on the alkenyl carbons will be converted into <strong>C-OH<\/strong> bonds.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-35268\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/08\/7-ozonolysis-of-alkenes-followed-by-treatment-with-oxidizing-agents-results-in-conversion-of-aldehydes-to-carboxylic-acids.gif\" alt=\"ozonolysis of alkenes followed by treatment with oxidizing agents results in conversion of aldehydes to carboxylic acids\" width=\"640\" height=\"341\" \/><\/a><\/p>\n<p>Here is a specific example:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-35269\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/08\/8-oxidative-cleavage-of-alkenes-with-oxidative-workup-H2O2-specific-example.gif\" alt=\"oxidative cleavage of alkenes with oxidative workup H2O2 specific example\" width=\"640\" height=\"326\" \/><\/a><\/p>\n<p>Note that the same transformation can be achieved by treating the alkene with hot, acidic KMnO<sub>4<\/sub>.<\/p>\n<h2><a id=\"four\"><\/a>4. Cyclic Alkenes<\/h2>\n<p>Ozonolysis of cyclic alkenes results in linear chains. For example, this ozonolysis of 1-methylcyclohexene gives the aldehyde-ketone below:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-35270\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/08\/9-ozonolysis-of-cyclic-alkenes-with-O3-results-in-chains-containing-aldehydes-or-ketones.gif\" alt=\"ozonolysis of cyclic alkenes with O3 results in chains containing aldehydes or ketones\" width=\"640\" height=\"263\" \/><\/a><\/p>\n<p>When dealing with these types of examples it can be <strong>very helpful<\/strong> to number your carbons and also to take your time with redrawing. My advice is to <strong>draw the ugly version first<\/strong>, [<span style=\"color: #993366;\"><em>See article:<\/em><\/span> <span style=\"color: #993366;\"><em><a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2011\/05\/31\/draw-the-ugly-version-first\/\">Draw the ugly version first<\/a><\/em><\/span>] to make sure you get the connectivity right, before trying to re-draw it neatly.<\/p>\n<p>See if you can predict the product of the following ozonolysis.<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35263\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35263\"] {\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=\"35263\"] {\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=\"35263\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35263\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35263 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35263\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-rc34p\" data-id=\"rc34p\">\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\/2540-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\/2540-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>It&#8217;s also helpful to be able to think\u00a0<em>in reverse<\/em>. Can you work backwards from the following product to the starting alkene?<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35264\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35264\"] {\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=\"35264\"] {\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=\"35264\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35264\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35264 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35264\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-zejae\" data-id=\"zejae\">\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\/2541-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\/2541-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<h2><a id=\"five\"><\/a>5. Ozonolysis of Molecules Containing Multiple Alkenes<\/h2>\n<p>When molecules with <strong>multiple<\/strong> alkenes are treated with O<sub>3<\/sub>, fragments will result.\u00a0 For example treatment of the triene below results in the following collection of carbonyl compounds:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-35271\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/08\/12-ozonolysis-of-a-molecule-with-multiple-alkenes-results-in-multiple-fragments.gif\" alt=\"ozonolysis of a molecule with multiple alkenes results in multiple fragments\" width=\"640\" height=\"271\" \/><\/a><\/p>\n<p>In olden days of yore,\u00a0 before our current powerful spectroscopic methods like nuclear magnetic resonance (NMR), a useful strategy for to determining the structure of unknown compounds was to subject them to cleavage with ozone, isolate and characterize the fragments, and then to do some detective work to put the pieces back together in the proper order. This type of structural analysis is known as degradation. (<span style=\"color: #800080;\"><em>For a typical example, see <a href=\"https:\/\/www.masterorganicchemistry.com\/2016\/08\/23\/structure-determination-case-study-deer-tarsal-gland-pheremone\/\">Case Study: Structure Determination of Deer Tarsal Gland Pheromone<\/a><\/em><\/span>)<\/p>\n<p>An example of a molecule with multiple alkenes that results in fragments after ozonolysis is shown below:<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35265\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35265\"] {\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=\"35265\"] {\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=\"35265\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35265\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35265 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35265\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-mfary\" data-id=\"mfary\">\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\/2542-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\/2542-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<h2><a id=\"six\"><\/a>6. Mechanism<\/h2>\n<p>The mechanism of ozonolysis took several decades to work out and involves a series of reactions that are <strong>not<\/strong> commonly encountered in introductory organic chemistry. So learning the mechanism of ozonolysis is going to feel a lot like memorization without understanding. Sorry in advance.<\/p>\n<p>In the first step, an alkene combines with ozone in a concerted reaction known as a cycloaddition. [<em><span style=\"color: #993366;\">The closest thing you will likely encounter to this reaction in introductory organic chemistry is the Diels-Alder reaction, which is a cousin of this process &#8211; <a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2017\/08\/30\/the-diels-alder-reaction\/\">See post &#8211; the Diels-Alder reaction<\/a><\/span> ]\u00a0<\/em>[<a href=\"#notefour\"><span style=\"color: #ff0000;\">Note 4<\/span><\/a>]<\/p>\n<p>The C-C pi bond breaks, and two new C-O bonds form.\u00a0 An unstable cyclic intermediate known as a &#8220;molozonide&#8221; forms, which has three consecutive oxygen atoms:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-35272\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/08\/14-Step-1-of-the-ozonolysis-of-alkenes-involves-a-concerted-cycloaddition-reaction-and-breakage-of-C-C-pi-bond-and-formation-of-new-C-O-bonds.gif\" alt=\"Step 1 of the ozonolysis of alkenes involves a concerted cycloaddition reaction and breakage of C-C pi bond and formation of new C-O bonds\" width=\"640\" height=\"331\" \/><\/a><\/p>\n<p>Molozonides have a very short lifetime. In the lab, they can be observed at temperatures around -100\u00b0C to -130\u00b0C [<a href=\"#refeleven\">ref<\/a>] but quickly break down in a reaction known as a <strong>reverse cycloaddition<\/strong>. The central C-C bond breaks, with simultaneous formation of two new C-O (pi) bonds.<\/p>\n<p>Two fragments result. The first one is a conventional carbonyl compound (either an aldehyde or ketone depending on structure). The second one is a <strong>zwitterionic\u00a0<\/strong>structure known as a carbonyl oxide (<span style=\"color: #800080;\"><em>although don&#8217;t worry if you can&#8217;t remember the name<\/em><\/span>).<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-38059\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2013\/04\/15-step-2-of-ozonolysis-of-alkenes-is-a-reverse-cycloaddition-to-give-carbonyl-and-carbonyl-oxide.gif\" alt=\"step 2 of ozonolysis of alkenes is a reverse cycloaddition to give carbonyl and carbonyl oxide\" width=\"600\" height=\"297\" \/><\/a><\/p>\n<p>What next? It turns out to be another cycloaddition [<a href=\"#notefive\">Note 5<\/a>] where the two fragments\u00a0<strong>recombine<\/strong> to give a new five-membered ring containing an ether linkage and a peroxide. This structure is commonly referred to as an <strong>ozonide<\/strong>.<span style=\"color: #800080;\"><em> although sometimes the term &#8220;1,2,4-trioxolane&#8221; is used<\/em><\/span>.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-35274\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/08\/16-step-3-of-the-ozonolysis-mechanism-is-a-formal-3-2-cycloaddition.gif\" alt=\"step 3 of the ozonolysis mechanism is a formal 3 +2 cycloaddition\" width=\"640\" height=\"324\" \/><\/a><\/p>\n<p>Ozonides can be,<\/p>\n<p>Upon warming, ozonides will break down to give aldehydes\/ketones, but because ozonides, just like organic peroxides, can be &#8221; &#8216;<a href=\"https:\/\/en.wiktionary.org\/wiki\/%27splodey#:~:text=Rhymes%3A%20%2D%C9%99%CA%8Adi-,Adjective,quotations%20%E2%96%BC\">splodey<\/a> &#8221; as some people would put it, they are best kept cold and in dilute solution, rather than isolated. <span style=\"color: #800080;\"><em>Apparently they can form nice crystals though!\u00a0<\/em><\/span><\/p>\n<p>For this reason ozonides are usually broken down at low temperature by adding a reducing agent, which breaks the weak O\u2013O bond and liberates the two carbonyl compounds, and also destroys any excess ozone.<\/p>\n<p>Two common reagents for reductive workup are dimethyl sulfide (DMS) and zinc.<\/p>\n<ul>\n<li>Reduction using dimethylsulfide has the advantage of generating benign dimethylsulfoxide (DMSO). To see a plausible mechanism, <a href=\"\" class=\"custom-tooltip\" data-image=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/08\/Supp-2-mechanism-for-the-reduction-of-ozonides-with-dimethyl-sulfide.gif\" data-link=\"\" data-title=\"\" data-text=\"\">Hover here for the mechanism<\/a> or click this <a href=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/08\/Supp-2-mechanism-for-the-reduction-of-ozonides-with-dimethyl-sulfide.gif\">link<\/a>.<\/li>\n<li>Reduction using acidic zinc results in zinc oxide (ZnO).\u00a0 To see a plausible mechanism, <a href=\"\" class=\"custom-tooltip\" data-image=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/08\/Supp-1-mechanism-for-the-reduction-of-ozonides-with-zinc.gif\" data-link=\"\" data-title=\"\" data-text=\"\">hover here<\/a> or click this <a href=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/08\/Supp-1-mechanism-for-the-reduction-of-ozonides-with-zinc.gif\">link<\/a>.<\/li>\n<\/ul>\n<p><span style=\"color: #800080;\"><em>In addition, triphenylphosphine (PPh<sub>3<\/sub>) can also be used, but from a practical perspective this tends to be a less popular choice owing to the difficulty of separating triphenylphosphine oxide (PPh<sub>3<\/sub>O) from the resulting product.\u00a0<\/em><\/span><\/p>\n<h2><a id=\"seven\"><\/a>7. Oxidative workup<\/h2>\n<p>Alternatively, allowing the ozonide to warm up in the presence of hydrogen peroxide (H<sub>2<\/sub>O<sub>2<\/sub>) will lead to the oxidation of any aldehydes to\u00a0<strong>carboxylic acids.\u00a0<\/strong><\/p>\n<p>For a possible mechanism (<span style=\"color: #800080;\"><em>generally not covered in introductory organic<\/em><\/span>) <a href=\"\" class=\"custom-tooltip\" data-image=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/08\/Supp-3-mechanism-for-the-oxidative-workup-of-ozonides-with-hydrogen-peroxide-to-give-carboxylic-acids.gif\" data-link=\"\" data-title=\"\" data-text=\"\">hover here<\/a> or click this <a href=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/08\/Supp-3-mechanism-for-the-oxidative-workup-of-ozonides-with-hydrogen-peroxide-to-give-carboxylic-acids.gif\">link<\/a>.<\/p>\n<h2><a id=\"eight\"><\/a>8. Alkynes<\/h2>\n<p>Alkynes can also undergo oxidative cleavage with O<sub>3<\/sub><span style=\"font-size: 16px;\"> to give carboxylic acids.\u00a0<\/span><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-35276\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/08\/17-treatment-of-alkynes-with-ozone-o3-results-in-carboxylic-acids.gif\" alt=\"treatment of alkynes with ozone o3 results in carboxylic acids\" width=\"640\" height=\"273\" \/><\/a><\/p>\n<p>Alkynes tend to be\u00a0<strong>less reactive\u00a0<\/strong>toward ozone than alkenes. There are plenty of examples of selective ozonolysis of an alkene in the presence of an alkyne. [<a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/jo9822941\">like here<\/a>]<\/p>\n<p>Ozonolysis of\u00a0<strong>terminal alkynes\u00a0<\/strong>(i.e. those that have a C-H bond) results in carbon dioxide. =<\/p>\n<p>Alkynes are more reactive than aromatic rings, however (<span style=\"color: #800080;\"><em>if you&#8217;re in Org 1, the special stability of aromatic rings like benzene is usually covered in Org 2 &#8211; see <a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/01\/20\/introduction-aromaticity\/\">Aromaticity<\/a><\/em><\/span>).<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-35275\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/08\/18-example-of-the-ozonolysis-of-alkynes-where-an-aromatic-ring-is-left-alone.gif\" alt=\"example of the ozonolysis of alkynes where an aromatic ring is left alone\" width=\"640\" height=\"309\" \/><\/a><\/p>\n<h2><a id=\"nine\"><\/a>9. Summary<\/h2>\n<p>The ozonolysis of alkenes and alkynes belongs to a class of reactions known as\u00a0<strong>oxidative cleavage.\u00a0<\/strong>Some other reactions in this family include the cleavage of vicinal diols by NaIO<sub>4<\/sub> or Pb(OAc)<sub>4<\/sub>, as well as the cleavage of alkenes with hot, acidic potassium permanganate (KMnO<sub>4<\/sub>).<\/p>\n<ul>\n<li>Make sure you understand the difference between reductive workup (leaves C-H bonds alone) and oxidative workup (oxidizes C-H bonds to C-OH bonds)<\/li>\n<li>Practice examples of the ozonolysis of cyclic alkenes. Don&#8217;t forget to count your carbons.<\/li>\n<li>Practice working backwards from ozonolysis products to the starting alkenes.<\/li>\n<li>In synthesis problems, be alert to the possibility of using alkenes as precursors to carbonyl compounds.<\/li>\n<\/ul>\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\/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\/2013\/06\/04\/oxidation-of-alkynes\/\" class=\"\"><span>Oxidation of Alkynes With O3 and KMnO4<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/reaction-guide\/oxidative-cleavage-of-alkenes-using-ozone-o3-to-ketones-and-aldehydes-reductive-workup\/\" class=\"\"><span>Ozonolysis of alkenes to ketones and aldehydes (reductive workup) (MOC Membership)<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/reaction-guide\/oxidative-cleavage-of-alkenes-to-give-ketonescarboxylic-acids-using-ozone-o3-oxidative-workup\/\" class=\"\"><span>Oxidative cleavage of alkenes to give ketones\/carboxylic acids using ozone (O3) \u2013 (\u201coxidative workup\u201d) (MOC Membership)<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/10\/21\/reagent-friday-sodium-periodate\/\" class=\"\"><span>Reagent Friday: Sodium Periodate<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2018\/02\/06\/wittig-reaction\/\" class=\"\"><span>Wittig Reaction<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/04\/25\/summary-alkene-reaction-pathways\/\" class=\"\"><span>Summary: Three Key Families Of Alkene Reaction Mechanisms<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/organic-chemistry-practice-problems\/alkene-reactions-practice-problems\/\" class=\"\"><span>Alkene Reactions Practice Problems<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/11\/25\/palladium-on-carbon-pdc\/\" class=\"\"><span>Palladium on Carbon (Pd\/C) for Catalytic Hydrogenation<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/01\/22\/alkene-addition-regioselectivity-syn-anti\/\" class=\"\"><span>Alkene Addition Reactions: \u201cRegioselectivity\u201d and \u201cStereoselectivity\u201d (Syn\/Anti)<\/span><\/a><\/li><\/ul><\/div>\n<p><strong><a id=\"noteone\"><\/a>Note 1.\u00a0<\/strong>These values are obtained from microwave spectroscopy. See Hughes, R. <em>J. Chem. Phys. <\/em>24, 131\u2013138 (<strong>1956<\/strong>).\u00a0<strong>DOI: <a href=\"https:\/\/doi.org\/10.1063\/1.1700813\">10.1063\/1.1700813<\/a><\/strong><\/p>\n<p><strong><a id=\"two\"><\/a>Note 2. <\/strong>Generally, more electron-rich alkenes (more substituted) undergo ozonolysis more quickly than electron-poor alkenes. When multiple reactive functional groups are present in a molecule, it is possible to obtain good selectivity through the use of appropriate <strong>dyes\u00a0<\/strong>such as Sudan Red (for an example, <a href=\"https:\/\/www.organic-chemistry.org\/totalsynthesis\/totsyn03\/azaspiracid-1-evans.shtm\">see here<\/a>)<\/p>\n<p><strong><a id=\"three\"><\/a>Note 3. <\/strong>Apparently the first isolation of an ozonide was made in 1873 by Houzeau, who obtained white, explosive crystals from the oxidative cleavage of benzene with ozone. [<a href=\"http:\/\/actachemscand.org\/pdf\/acta_vol_21_p1229-1233.pdf\">Ref<\/a>]<\/p>\n<p><strong><a id=\"four\"><\/a>Note 4.\u00a0<\/strong>Technically this is a &#8220;1,3-dipolar cycloaddition&#8221; reaction, a process similar to the Diels-Alder in which a 4 pi-electron component undergoes a cycloaddition with a 2 pi-electron component. One key difference in this case is that it operates with &#8220;inverse electron demand&#8221;; in contrast to the normal Diels-Alder, which is fastest with electron-rich dienes and electron-poor dienophiles, the reaction with ozone operates fastest with electron-rich alkenes.<\/p>\n<p><strong><a id=\"five\"><\/a>Note 5. <\/strong>Another 1,3-dipolar cycloaddition, this time between a carbonyl oxide and a carbonyl. For some fairly conclusive evidence that this step is a concerted cycloaddition and not a two-step series of 1,2-addition reactions snapping shut to give a five-membered ring, see [<a href=\"#refseven\">ref<\/a>]. This recombination step is stereoselective and dependent on starting alkene geometry.<\/p>\n<p><strong>Note 6.<\/strong> Ozonides are not generally a class of compound you would want to work with, but the naturally occurring ozonide <a href=\"https:\/\/en.wikipedia.org\/wiki\/Artemisinin\">arteminisin<\/a> is a known antimalarial drug. The ozonide functional group is key to its activity.\u00a0 Other derivatives of arteminisin have been developed as drug candidates.<\/p>\n<p>For a short, fun article on developments on this field, see: &#8220;<a href=\"https:\/\/www.science.org\/content\/blog-post\/ozonides-drugs-what-will-they-think-next\"><strong>Ozonides as Drugs: What Will They Think of Next?<\/strong><\/a>&#8221; by Derek Lowe.<\/p>\n<hr \/>\n<h2><a id=\"quiz\"><\/a>Quiz Yourself!<\/h2>\n<p>&nbsp;<br \/>\n<\/p>\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/3589-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\/2558-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <br \/>\n<\/p>\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0489-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <br \/>\n<\/p>\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0491-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<br \/>\n<\/p>\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0492-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <br \/>\n<\/p>\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0494-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <br \/>\n<\/p>\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0496-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n<hr \/>\n<h2><a id=\"furtherreading\"><\/a>(Advanced) References and Further Reading<\/h2>\n<p>A fun article on the history of the discovery of ozone written by Mordecai B. Rubin is found here, from the Bulletin of Chemical History. [<a href=\"http:\/\/www.scs.uiuc.edu\/~mainzv\/HIST\/awards\/OPA%20Papers\/2001-Rubin.pdf\">PDF<\/a>]<\/p>\n<ol>\n<li><strong>Ueber die Einwirkung des Ozons auf organische Verbindungen<br \/>\n<\/strong> Harries<br \/>\n<em>Just. Lieb. Ann. Chem.<\/em> <em>1905<\/em>, <em>343<\/em> (2-3), 311-344<br \/>\n<strong>DOI: <\/strong><a href=\"https:\/\/onlinelibrary.wiley.com\/doi\/abs\/10.1002\/jlac.19053430209\">10.1002\/jlac.19053430209<\/a><br \/>\nThe first paper describing the oxidative cleavage of unsaturated compounds with ozone in solution.<\/li>\n<li><strong>OZONE<br \/>\n<\/strong> I. Smith, F. L. Greenwood, and O. Hudrlik<strong><br \/>\n<\/strong><em>Org. Synth. <\/em><strong>1946<\/strong> <em>26<\/em>, 63<strong><br \/>\nDOI: <\/strong><a href=\"http:\/\/www.orgsyn.org\/demo.aspx?prep=CV3P0673\">10.15227\/orgsyn.026.0063<\/a><br \/>\nThis procedure from <em>Organic Syntheses, <\/em>a source of reliable, reproducible and independently tested organic chemistry laboratory experimental procedures, provides a detailed explanation of how to build a laboratory ozonizer.<\/li>\n<li><strong>The Preparation of Aldehydes, Ketones, and Acids by Ozone Oxidation<br \/>\n<\/strong>Albert L. Henne and Philip Hill<br \/>\n<em>Journal of the American Chemical Society<\/em> <strong>1943<\/strong> <em>65<\/em> (5), 752-754<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja01245a003\">1021\/ja01245a003<\/a><br \/>\nThis paper shows that carboxylic acids are formed in good yields from aldehydes when the ozonolysis reaction mixture is worked up in the presence of excess hydrogen peroxide.<\/li>\n<li><strong>Notes- A Convenient Method for Reduction of Hydroperoxide Ozonation Products<br \/>\n<\/strong> Knowles and Q. Thompson<strong><br \/>\n<\/strong><em>The Journal of Organic Chemistry<\/em><strong> 1960 <\/strong><em>25<\/em> (6), 1031-1033<br \/>\n<strong>DOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/jo01076a044\">10.1021\/jo01076a044<\/a><br \/>\nAlthough the current practice is to use dimethyl sulfide in a reductive ozonolysis workup, trimethyl phosphite can also be used, as this paper from Nobel Laureate W. S. Knowles demonstrates.<\/li>\n<li><strong>OZONOLYTIC CLEAVAGE OF CYCLOHEXENE TO TERMINALLY DIFFERENTIATED PRODUCTS: METHYL 6-OXOHEXANOATE, 6,6-DIMETHOXYHEXANAL, METHYL 6,6-DIMETHOXYHEXANOATE<br \/>\n<\/strong>Ronald E. Claus and Stuart L. Schreiber<br \/>\n<em>Org. Synth.<\/em> <strong>1986<\/strong>, <em>64<\/em>, 150<br \/>\n<strong>DOI: <\/strong><a href=\"http:\/\/www.orgsyn.org\/demo.aspx?prep=CV7P0168\">10.15227\/orgsyn.064.0150<\/a><br \/>\nThis procedure in <em>Organic Syntheses<\/em> demonstrates how ozonolysis can be used to quickly generate differentiated bifunctional compounds.<\/li>\n<li><strong>Mechanism of Ozonolysis<br \/>\n<\/strong> Dr. Rudolf Criegee<strong><br \/>\n<\/strong><em>Angew. Chem. Int. Ed.<\/em> <strong>1975<\/strong>, <em>14<\/em> (11), 745-752<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/onlinelibrary.wiley.com\/doi\/abs\/10.1002\/anie.197507451\">10.1002\/anie.197507451<\/a><br \/>\nThis is an account by Prof. Rudolf Criegee on work done towards determining the mechanism of ozonolysis. Criegee himself carried out extensive work in this area \u2013 the \u2018Criegee intermediate\u2019 in ozonolysis is named after him.The following papers are further mechanistic studies on ozonolysis:<\/li>\n<li><strong><a id=\"refseven\"><\/a>Formation and Structure of Ozonides<\/strong>\n<div>Robert L. Kuczkowski<\/div>\n<div><cite>Accounts of Chemical Research<\/cite>\u00a0<strong>1983<\/strong>\u00a0<em>16<\/em>\u00a0(2), 42-47<br \/>\n<strong>DOI:<\/strong> 1<a href=\"https:\/\/pubs.acs.org\/doi\/epdf\/10.1021\/ar00086a002\">0.1021\/ar00086a002<\/a><br \/>\nA good overview on evidence for the the various steps of the ozonolysis reaction.<\/div>\n<\/li>\n<li><strong>New evidence in the mechanism of ozonolysis of olefins<br \/>\n<\/strong> Klopman and C. M. Joiner<strong><br \/>\n<\/strong><em>Journal of the American Chemical Society<\/em> <strong>1975<\/strong> <em>97<\/em> (18), 5287-5288<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00851a049\">10.1021\/ja00851a049<\/a><\/li>\n<li><strong>Mechanism of ozonolysis. (a) Microwave spectra, structures, and dipole moments of propylene and trans-2-butene ozonides. (b) Orbital symmetry analysis<\/strong><br \/>\nRobert P. Lattimer, Robert L. Kuczkowski, and Charles W. Gillies<br \/>\n<em>Journal of the American Chemical Society<\/em> <strong>1974<\/strong> <em>96<\/em> (2), 348-358<br \/>\n<strong>DOI:<\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00809a006\">1021\/ja00809a006<\/a><\/li>\n<li><strong>Stereospecificity in ozonide and cross-ozonide formation<\/strong>\n<div>Nathan L. Bauld, James A. Thompson, Charles E. Hudson, and Philip S. Bailey<\/div>\n<div><cite>Journal of the American Chemical Society<\/cite>\u00a0<strong>1968<\/strong>\u00a0<em>90<\/em>\u00a0(7), 1822-1830<\/div>\n<p><strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/ja01009a026\">10.1021\/ja01009a026<\/a><\/li>\n<li><strong><a id=\"refeleven\"><\/a>Ozonolysis. X. Molozonide as an intermediate in the ozonolysis of cis- and trans-alkenes<\/strong><br \/>\nLois J. Durham and Fred L. Greenwood<br \/>\n<em>The Journal of Organic Chemistry<\/em> <strong>1968<\/strong> 33 (4), 1629-1632<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/jo01268a068\">10.1021\/jo01268a068<\/a><br \/>\nEvidence for the formation of a molozonide, which decomposes at -130\u00b0C (<em>cis<\/em>) or -100\u00b0C (<em>trans<\/em>) depending on the stereochemistry of the alkene.<\/li>\n<\/ol>\n","protected":false},"excerpt":{"rendered":"<p>Ozonolysis of Alkenes and Alkynes\u00a0 Alkenes can undergo oxidative cleavage\u00a0with ozone (O3) to give carbonyl compounds, cleaving the C=C bond The reaction generates an\u00a0ozonide intermediate, <\/p>\n","protected":false},"author":1,"featured_media":35281,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1418],"tags":[918,919,535,448,251,295,447,451],"post_folder":[],"class_list":["post-7238","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-alkene-reactions","tag-carbonyl","tag-carboxylic-acid","tag-kmno4","tag-o3","tag-oxidation","tag-oxidative-cleavage","tag-ozone","tag-ozonolysis"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Alkene Reactions: Ozonolysis &#8211; Master Organic Chemistry<\/title>\n<meta name=\"description\" content=\"Ozonolysis with O3 converts alkenes into carbonyl compounds. 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