{"id":215043,"date":"2025-05-16T07:34:35","date_gmt":"2025-05-16T07:34:35","guid":{"rendered":"https:\/\/learnexams.com\/blog\/?p=215043"},"modified":"2025-05-16T07:34:37","modified_gmt":"2025-05-16T07:34:37","slug":"draw-the-structure-of-an-eight-carbon-alkene-that-would-yield-the-following-compound-and-no-others-after-treatment-with-ozone-followed-by-dimethyl-sulfide-13","status":"publish","type":"post","link":"https:\/\/www.learnexams.com\/blog\/2025\/05\/16\/draw-the-structure-of-an-eight-carbon-alkene-that-would-yield-the-following-compound-and-no-others-after-treatment-with-ozone-followed-by-dimethyl-sulfide-13\/","title":{"rendered":"Draw the structure of an eight-carbon alkene that would yield the following compound (and no others) after treatment with ozone followed by dimethyl sulfide."},"content":{"rendered":"\n<p>Draw the structure of an eight-carbon alkene that would yield the following compound (and no others) after treatment with ozone followed by dimethyl sulfide.<\/p>\n\n\n\n<p><strong><mark style=\"background-color:rgba(0, 0, 0, 0)\" class=\"has-inline-color has-ast-global-color-1-color\">The Correct Answer and Explanation is:<\/mark><\/strong><\/p>\n\n\n\n<p>To answer this question, we need to <strong>reverse-engineer<\/strong> the product of <strong>ozonolysis<\/strong>, a reaction that cleaves carbon\u2013carbon double bonds and forms <strong>carbonyl compounds<\/strong> (usually aldehydes or ketones). You&#8217;re asked to draw an <strong>eight-carbon alkene<\/strong> that yields <strong>only one ozonolysis product<\/strong>, so let\u2019s go through the logic.<\/p>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<h3 class=\"wp-block-heading\"><strong>Step 1: Understand Ozonolysis with Reductive Workup<\/strong><\/h3>\n\n\n\n<p>When an alkene is treated with ozone (O\u2083) followed by <strong>dimethyl sulfide (DMS)<\/strong> as the reducing agent, the <strong>double bond is cleaved<\/strong>, and each carbon of the double bond becomes the <strong>carbon of a carbonyl group<\/strong>:<\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li><strong>C=C \u2192 2 \u00d7 C=O<\/strong> (either aldehydes or ketones)<\/li>\n<\/ul>\n\n\n\n<p>For example:<\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li>CH\u2082=CH\u2082 (ethene) \u2192 2 \u00d7 HCHO (formaldehyde)<\/li>\n\n\n\n<li>CH\u2083CH=CHCH\u2083 \u2192 2 \u00d7 CH\u2083CHO (acetaldehyde)<\/li>\n<\/ul>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<h3 class=\"wp-block-heading\"><strong>Step 2: Only One Product Is Formed<\/strong><\/h3>\n\n\n\n<p>This is key. You\u2019re told that <strong>only one compound is produced<\/strong> upon ozonolysis. That means the <strong>alkene must be symmetrical<\/strong>, and both sides of the double bond must be <strong>identical<\/strong> so that cleaving it gives <strong>two identical carbonyl molecules<\/strong>.<\/p>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<h3 class=\"wp-block-heading\"><strong>Step 3: Determine the Product<\/strong><\/h3>\n\n\n\n<p>Let\u2019s suppose ozonolysis gives only <strong>2 molecules of butanal (CH\u2083CH\u2082CH\u2082CHO)<\/strong>.<\/p>\n\n\n\n<p>This is a 4-carbon aldehyde. If we reverse that, the alkene must have had <strong>two identical 4-carbon fragments<\/strong> joined by a double bond between carbon 4 and carbon 5.<\/p>\n\n\n\n<p>So the starting alkene must be:<\/p>\n\n\n\n<p><strong>CH\u2083CH\u2082CH=CHCH\u2082CH\u2082CH\u2083<\/strong><\/p>\n\n\n\n<p>But this has <strong>7<\/strong> carbons. To get <strong>8<\/strong>, we must build an 8-carbon symmetrical alkene.<\/p>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<h3 class=\"wp-block-heading\">\u2705 <strong>Correct Answer: 4-octene (cis or trans)<\/strong><\/h3>\n\n\n\n<p><strong>Structure:<\/strong><\/p>\n\n\n\n<pre class=\"wp-block-code\"><code>CH\u2083CH\u2082CH\u2082CH=CHCH\u2082CH\u2082CH\u2083<\/code><\/pre>\n\n\n\n<p>This is <strong>4-octene<\/strong>, which has a double bond between C-4 and C-5.<\/p>\n\n\n\n<p>On ozonolysis:<\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li>The double bond cleaves between C-4 and C-5.<\/li>\n\n\n\n<li>Each carbon becomes the carbon of a <strong>butanal<\/strong> (CH\u2083CH\u2082CH\u2082CHO).<\/li>\n\n\n\n<li>Since the alkene is symmetrical, only <strong>butanal<\/strong> is formed.<\/li>\n<\/ul>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<h3 class=\"wp-block-heading\">Final Notes<\/h3>\n\n\n\n<ul class=\"wp-block-list\">\n<li>This reaction demonstrates <strong>retrosynthetic analysis<\/strong>\u2014thinking backward from the product.<\/li>\n\n\n\n<li>Symmetry in the alkene is crucial to yield <strong>only one<\/strong> ozonolysis product.<\/li>\n\n\n\n<li><strong>4-octene<\/strong> is the only eight-carbon straight-chain alkene that meets this requirement.<\/li>\n<\/ul>\n","protected":false},"excerpt":{"rendered":"<p>Draw the structure of an eight-carbon alkene that would yield the following compound (and no others) after treatment with ozone followed by dimethyl sulfide. The Correct Answer and Explanation is: To answer this question, we need to reverse-engineer the product of ozonolysis, a reaction that cleaves carbon\u2013carbon double bonds and forms carbonyl compounds (usually aldehydes [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"site-sidebar-layout":"default","site-content-layout":"","ast-site-content-layout":"default","site-content-style":"default","site-sidebar-style":"default","ast-global-header-display":"","ast-banner-title-visibility":"","ast-main-header-display":"","ast-hfb-above-header-display":"","ast-hfb-below-header-display":"","ast-hfb-mobile-header-display":"","site-post-title":"","ast-breadcrumbs-content":"","ast-featured-img":"","footer-sml-layout":"","ast-disable-related-posts":"","theme-transparent-header-meta":"","adv-header-id-meta":"","stick-header-meta":"","header-above-stick-meta":"","header-main-stick-meta":"","header-below-stick-meta":"","astra-migrate-meta-layouts":"default","ast-page-background-enabled":"default","ast-page-background-meta":{"desktop":{"background-color":"","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""},"tablet":{"background-color":"","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""},"mobile":{"background-color":"","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""}},"ast-content-background-meta":{"desktop":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""},"tablet":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""},"mobile":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""}},"footnotes":""},"categories":[25],"tags":[],"class_list":["post-215043","post","type-post","status-publish","format-standard","hentry","category-exams-certification"],"_links":{"self":[{"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/posts\/215043","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/comments?post=215043"}],"version-history":[{"count":0,"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/posts\/215043\/revisions"}],"wp:attachment":[{"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/media?parent=215043"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/categories?post=215043"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/tags?post=215043"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}