{"id":208682,"date":"2025-04-28T04:32:58","date_gmt":"2025-04-28T04:32:58","guid":{"rendered":"https:\/\/learnexams.com\/blog\/?p=208682"},"modified":"2025-04-28T04:33:00","modified_gmt":"2025-04-28T04:33:00","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-11","status":"publish","type":"post","link":"https:\/\/www.learnexams.com\/blog\/2025\/04\/28\/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-11\/","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><mark style=\"background-color:rgba(0, 0, 0, 0)\" class=\"has-inline-color has-ast-global-color-6-color\"><strong>The correct answer and explanation is :<\/strong><\/mark><\/p>\n\n\n\n<p><strong>First<\/strong>, the question says:<\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li>We have an <strong>8-carbon alkene<\/strong>.<\/li>\n\n\n\n<li>After <strong>ozonolysis<\/strong> (ozone followed by <strong>dimethyl sulfide<\/strong>, which is a <em>reductive<\/em> workup), it yields <strong>a single compound<\/strong> (and no others).<\/li>\n<\/ul>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<p>When an alkene undergoes <strong>ozonolysis + reductive workup<\/strong>, <strong>each carbon-carbon double bond<\/strong> is <strong>cleaved<\/strong>, and <strong>each carbon of the double bond<\/strong> becomes a <strong>carbonyl group<\/strong> (C=O).<br>Depending on the position of the double bond, ozonolysis produces:<\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li>Aldehydes (if the double-bonded carbon is bonded to at least one H)<\/li>\n\n\n\n<li>Ketones (if the double-bonded carbon is bonded to two carbons)<\/li>\n<\/ul>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<p><strong>Now<\/strong>, since <strong>only one product<\/strong> forms after ozonolysis, <strong>both halves after cleavage must be identical<\/strong> \u2014 <strong>symmetrical<\/strong>.<\/p>\n\n\n\n<p>Thus, the alkene must be <strong>symmetrical<\/strong> around the double bond.<\/p>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<p><strong>Let&#8217;s work through it:<\/strong><\/p>\n\n\n\n<p>We need an 8-carbon alkene, symmetrical, so after ozonolysis, the two pieces are the same.<\/p>\n\n\n\n<p>Suppose we choose <strong>4 carbons on each side<\/strong> of the double bond.<br>Thus, the structure is:<\/p>\n\n\n\n<blockquote class=\"wp-block-quote is-layout-flow wp-block-quote-is-layout-flow\">\n<p><strong>CH\u2083\u2013CH\u2082\u2013CH\u2082\u2013CH=CH\u2013CH\u2082\u2013CH\u2082\u2013CH\u2083<\/strong><\/p>\n<\/blockquote>\n\n\n\n<p>This is <strong>4-octene<\/strong>, specifically the <strong>trans-4-octene<\/strong> or <strong>cis-4-octene<\/strong> form.<\/p>\n\n\n\n<p>After ozonolysis:<\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li>The C=C bond between C4 and C5 is cleaved.<\/li>\n\n\n\n<li>Each side becomes a carbonyl group.<\/li>\n\n\n\n<li>Thus, we get two identical fragments: <strong>butanal (CH\u2083\u2013CH\u2082\u2013CH\u2082\u2013CHO)<\/strong><\/li>\n<\/ul>\n\n\n\n<p><strong>Butanal<\/strong> is an aldehyde (4 carbons).<\/p>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<h3 class=\"wp-block-heading\"><strong>Final Answer:<\/strong><\/h3>\n\n\n\n<p>The structure of the starting alkene is <strong>4-octene<\/strong>:<\/p>\n\n\n\n<p><strong>Structure:<\/strong><\/p>\n\n\n\n<pre class=\"wp-block-code\"><code>CH\u2083\u2013CH\u2082\u2013CH\u2082\u2013CH=CH\u2013CH\u2082\u2013CH\u2082\u2013CH\u2083<\/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>Full Explanation (300 words)<\/strong><\/h3>\n\n\n\n<p>When an alkene undergoes ozonolysis followed by reductive workup (dimethyl sulfide), the carbon-carbon double bond is cleaved and each carbon formerly involved in the double bond becomes a carbonyl group. If an alkene yields only a single product after this process, it indicates that the molecule must be symmetrical, meaning the two sides of the double bond are identical. Since the alkene must have eight carbons and produce only one product, it must be symmetrically arranged around the double bond.<\/p>\n\n\n\n<p>4-octene fits these criteria perfectly. Its structure, CH\u2083\u2013CH\u2082\u2013CH\u2082\u2013CH=CH\u2013CH\u2082\u2013CH\u2082\u2013CH\u2083, places the double bond between the fourth and fifth carbons, ensuring symmetry. Upon ozonolysis, the double bond is cleaved, and each carbon atom at the cleavage point is converted into an aldehyde group. The resulting product is butanal (CH\u2083\u2013CH\u2082\u2013CH\u2082\u2013CHO), a four-carbon aldehyde. Since the molecule was symmetric, the same product is generated from both sides of the original double bond, leading to only one distinct compound after ozonolysis.<\/p>\n\n\n\n<p>If the starting material had been asymmetric (e.g., with different groups on either side of the double bond), two different products would have resulted, which contradicts the problem\u2019s statement. Therefore, <strong>4-octene<\/strong> is the correct and only answer that matches all conditions provided.<\/p>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\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 : First, the question says: When an alkene undergoes ozonolysis + reductive workup, each carbon-carbon double bond is cleaved, and each carbon of the double [&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-208682","post","type-post","status-publish","format-standard","hentry","category-exams-certification"],"_links":{"self":[{"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/posts\/208682","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=208682"}],"version-history":[{"count":0,"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/posts\/208682\/revisions"}],"wp:attachment":[{"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/media?parent=208682"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/categories?post=208682"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/tags?post=208682"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}