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
The Correct Answer and Explanation is:<\/mark><\/strong><\/p>\n\n\n\n To answer this question, we need to understand ozonolysis<\/strong> of alkenes and how to work backward from the ozonolysis products to identify the original alkene.<\/p>\n\n\n\n Ozonolysis is an organic reaction where an alkene is cleaved by ozone (O\u2083), resulting in two carbonyl compounds<\/strong>, typically aldehydes or ketones. When the reaction is followed by a reductive workup (e.g., with dimethyl sulfide<\/strong>, DMS), each double bond is split and replaced with a C=O group.<\/p>\n\n\n\n You’re told that ozonolysis followed by dimethyl sulfide yields a single product<\/strong> \u2014 that is, only one kind of carbonyl compound<\/strong>. This suggests symmetry<\/strong> in the molecule, because cleaving a double bond yields identical fragments<\/strong>.<\/p>\n\n\n\n So, we are to draw an eight-carbon alkene<\/strong> that, upon ozonolysis and reduction with DMS, produces a single carbonyl compound<\/strong>.<\/p>\n\n\n\n Let\u2019s assume the ozonolysis yields only 2 molecules of butanal (CH\u2083CH\u2082CH\u2082CHO)<\/strong>. That means the original alkene must be symmetric and must split into two butanal molecules<\/strong>.<\/p>\n\n\n\n Butanal has 4 carbons. If two butanal molecules are formed from a single alkene, the original compound must be oct-4-ene<\/strong> (CH\u2083CH\u2082CH=CHCH\u2082CH\u2082CH\u2083), a symmetric alkene with the double bond at the center.<\/p>\n\n\n\n The original alkene is oct-4-ene<\/strong>, which has the structure:<\/p>\n\n\n\n This satisfies the requirement that only one compound is formed<\/strong> after ozonolysis and dimethyl sulfide treatment.<\/p>\n","protected":false},"excerpt":{"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. The Correct Answer and Explanation is: To answer this question, we need to understand ozonolysis of alkenes and how to work backward from the ozonolysis products to identify the original alkene. […]<\/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-215999","post","type-post","status-publish","format-standard","hentry","category-exams-certification"],"_links":{"self":[{"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/posts\/215999","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=215999"}],"version-history":[{"count":0,"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/posts\/215999\/revisions"}],"wp:attachment":[{"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/media?parent=215999"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/categories?post=215999"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/tags?post=215999"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}Step-by-step reasoning:<\/h3>\n\n\n\n
1. Understanding Ozonolysis<\/strong><\/h4>\n\n\n\n
2. What Information Is Given?<\/strong><\/h4>\n\n\n\n
3. Work Backward from the Product<\/strong><\/h4>\n\n\n\n
4. Combine the Two Butanal Units<\/strong><\/h4>\n\n\n\n
\u2705 Correct Answer:<\/h3>\n\n\n\n
CH\u2083\u2013CH\u2082\u2013CH\u2082\u2013CH=CH\u2013CH\u2082\u2013CH\u2082\u2013CH\u2083<\/code><\/pre>\n\n\n\nWhy This Works:<\/h3>\n\n\n\n