{"id":219168,"date":"2025-05-25T19:01:49","date_gmt":"2025-05-25T19:01:49","guid":{"rendered":"https:\/\/learnexams.com\/blog\/?p=219168"},"modified":"2025-05-25T19:01:52","modified_gmt":"2025-05-25T19:01:52","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-21","status":"publish","type":"post","link":"https:\/\/www.learnexams.com\/blog\/2025\/05\/25\/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-21\/","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

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

Correct Answer:<\/strong><\/p>\n\n\n\n

The compound formed after ozonolysis is two molecules of butanal (CH\u2083CH\u2082CH\u2082CHO)<\/strong>. The only eight-carbon alkene that yields exclusively this product is 3-octene<\/strong>.<\/p>\n\n\n\n

Structure of 3-octene:<\/strong><\/p>\n\n\n\n

CH\u2083\u2013CH\u2082\u2013CH=CH\u2013CH\u2082\u2013CH\u2082\u2013CH\u2082\u2013CH\u2083\n         \u2191     \u2191\n       C3    C4\n<\/code><\/pre>\n\n\n\n
\n\n\n\n
Explanation<\/strong><\/p>\n\n\n\n
Ozonolysis is a powerful oxidative cleavage reaction that breaks double bonds in alkenes and forms carbonyl-containing products\u2014either aldehydes or ketones. The outcome depends on the substituents attached to the alkene carbons. When the reaction is followed by a reducing agent such as dimethyl sulfide (DMS, (CH\u2083)\u2082S)<\/strong>, aldehydes and ketones are formed instead of carboxylic acids.<\/p>\n\n\n\n
The problem states that ozonolysis of an eight-carbon alkene produces a single product<\/strong>, and that product is butanal<\/strong>. Butanal is a 4-carbon aldehyde: CH\u2083CH\u2082CH\u2082CHO. Since ozonolysis cleaves the carbon-carbon double bond and converts each alkene carbon into a carbonyl group, the presence of two identical aldehydes<\/strong> implies that the double bond was symmetrically located in the alkene.<\/p>\n\n\n\n
Let\u2019s analyze 3-octene:<\/p>\n\n\n\n
    \n
  • Molecular formula: C\u2088H\u2081\u2086<\/li>\n\n\n\n
  • Double bond is between C3 and C4: CH\u2083\u2013CH\u2082\u2013CH=CH\u2013CH\u2082\u2013CH\u2082\u2013CH\u2082\u2013CH\u2083<\/li>\n\n\n\n
  • Upon ozonolysis, this double bond is cleaved, and each carbon becomes the carbon of an aldehyde group.<\/li>\n\n\n\n
  • The cleavage occurs between C3 and C4, forming:\n
      \n
    • From C1\u2013C3: CH\u2083\u2013CH\u2082\u2013CH (\u2192 CHO) \u2192 CH\u2083CH\u2082CH\u2082CHO (butanal)<\/strong><\/li>\n\n\n\n
    • From C4\u2013C8: CH (\u2192 CHO)\u2013CH\u2082\u2013CH\u2082\u2013CH\u2083 \u2192 CH\u2083CH\u2082CH\u2082CHO (butanal)<\/strong><\/li>\n<\/ul>\n<\/li>\n<\/ul>\n\n\n\n
      Since both halves are the same, the only product is butanal<\/strong>.<\/p>\n\n\n\n
      Any other isomeric alkene (e.g., 2-octene, 4-octene) would result in either mixed aldehydes or ketones, violating the \u201cno other products\u201d condition. Therefore, 3-octene<\/strong> is the only correct structure that yields only butanal<\/strong> upon ozonolysis with DMS.<\/p>\n\n\n\n
      \"\"<\/figure>\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: Correct Answer: The compound formed after ozonolysis is two molecules of butanal (CH\u2083CH\u2082CH\u2082CHO). The only eight-carbon alkene that yields exclusively this product is 3-octene. Structure […]<\/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-219168","post","type-post","status-publish","format-standard","hentry","category-exams-certification"],"_links":{"self":[{"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/posts\/219168","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=219168"}],"version-history":[{"count":0,"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/posts\/219168\/revisions"}],"wp:attachment":[{"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/media?parent=219168"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/categories?post=219168"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/tags?post=219168"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}