{"id":221370,"date":"2025-05-29T12:47:03","date_gmt":"2025-05-29T12:47:03","guid":{"rendered":"https:\/\/learnexams.com\/blog\/?p=221370"},"modified":"2025-05-29T12:47:05","modified_gmt":"2025-05-29T12:47:05","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-23","status":"publish","type":"post","link":"https:\/\/www.learnexams.com\/blog\/2025\/05\/29\/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-23\/","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 class=\"wp-block-paragraph\">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 class=\"wp-block-paragraph\"><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 class=\"wp-block-paragraph\"><strong>Correct Answer:<\/strong><\/p>\n\n\n\n<p class=\"wp-block-paragraph\">The product after ozonolysis is:<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>2 molecules of butanal<\/strong> (CH\u2083CH\u2082CH\u2082CHO)<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">To yield only <strong>butanal<\/strong> (an aldehyde with four carbon atoms), the original alkene must cleave symmetrically into <strong>two identical four-carbon fragments<\/strong>.<\/p>\n\n\n\n<h3 class=\"wp-block-heading\"><strong>Structure of the Alkene:<\/strong><\/h3>\n\n\n\n<p class=\"wp-block-paragraph\">The only eight-carbon alkene that will give two molecules of <strong>butanal<\/strong> upon ozonolysis is:<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>3-octene (cis or trans)<\/strong><\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>Structure of 3-octene:<\/strong><\/p>\n\n\n\n<pre class=\"wp-block-code\"><code>CH\u2083CH\u2082CH=CHCH\u2082CH\u2082CH\u2083\n<\/code><\/pre>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<h3 class=\"wp-block-heading\"><strong>Explanation<\/strong><\/h3>\n\n\n\n<p class=\"wp-block-paragraph\">Ozonolysis is a powerful oxidative cleavage reaction used to break double bonds in alkenes. It involves the reaction of ozone (O\u2083) with the carbon-carbon double bond (C=C), resulting in the cleavage of the double bond and formation of two carbonyl-containing fragments \u2014 aldehydes or ketones depending on the substitution of the double bond.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">After ozonolysis, if dimethyl sulfide (DMS, (CH\u2083)\u2082S) is used as the reducing agent, any ozonide intermediate is reduced to <strong>aldehydes<\/strong> or <strong>ketones<\/strong>, without further oxidation (i.e., no carboxylic acids form).<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">In this question, the <strong>only ozonolysis product<\/strong> is <strong>butanal (CH\u2083CH\u2082CH\u2082CHO)<\/strong> \u2014 an aldehyde with four carbon atoms. Since ozonolysis cleaves a double bond into two carbonyl fragments, the original alkene must have been split at the double bond to form <strong>two identical butanal molecules<\/strong>.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">To get two <strong>butanal<\/strong> molecules, the original alkene must be symmetrical, with the double bond located such that each resulting fragment has four carbons.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">Therefore, the original alkene is:<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>3-octene<\/strong>, with the structure:<\/p>\n\n\n\n<pre class=\"wp-block-code\"><code>CH\u2083CH\u2082CH=CHCH\u2082CH\u2082CH\u2083\n<\/code><\/pre>\n\n\n\n<p class=\"wp-block-paragraph\">Upon ozonolysis:<\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li>The double bond between carbon 3 and carbon 4 is cleaved.<\/li>\n\n\n\n<li>Each side becomes a <strong>butanal<\/strong> molecule (CH\u2083CH\u2082CH\u2082CHO).<\/li>\n<\/ul>\n\n\n\n<p class=\"wp-block-paragraph\">No other carbonyl compounds are formed, making 3-octene the <strong>only<\/strong> correct structure for this scenario. Both cis- and trans-3-octene would yield the same products under these conditions.<\/p>\n\n\n\n<figure class=\"wp-block-image size-full\"><img decoding=\"async\" src=\"https:\/\/learnexams.com\/blog\/wp-content\/uploads\/2025\/05\/learnexams-banner7-101.jpeg\" alt=\"\" class=\"wp-image-221371\"\/><\/figure>\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: Correct Answer: The product after ozonolysis is: 2 molecules of butanal (CH\u2083CH\u2082CH\u2082CHO) To yield only butanal (an aldehyde with four carbon atoms), the original alkene [&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-221370","post","type-post","status-publish","format-standard","hentry","category-exams-certification"],"_links":{"self":[{"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/posts\/221370","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=221370"}],"version-history":[{"count":0,"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/posts\/221370\/revisions"}],"wp:attachment":[{"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/media?parent=221370"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/categories?post=221370"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/tags?post=221370"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}