{"id":222547,"date":"2025-05-31T12:52:40","date_gmt":"2025-05-31T12:52:40","guid":{"rendered":"https:\/\/learnexams.com\/blog\/?p=222547"},"modified":"2025-05-31T12:52:42","modified_gmt":"2025-05-31T12:52:42","slug":"lion-indicate-whether-the-use-of-wedge-and-dash-bonds-are-required-when-drawing-the-product-of-using","status":"publish","type":"post","link":"https:\/\/www.learnexams.com\/blog\/2025\/05\/31\/lion-indicate-whether-the-use-of-wedge-and-dash-bonds-are-required-when-drawing-the-product-of-using\/","title":{"rendered":"Lion Indicate whether the use of wedge and dash bonds are required when drawing the product of using"},"content":{"rendered":"\n

Lion Indicate whether the use of wedge and dash bonds are required when drawing the product of using: 1-methylcyclohexene as your starting material with: A) hydroboration-oxidation yes no B) hydrogenation with a metal catalyst using protium yes no C) hydrogenation with a metal catalyst using deuterium yes no D) free radical addition of HBr yes no E) vicinal dihalide formation yes no F) electrophilic addition of HX yes no G) vicinal halohydrin formation yes no H) hydration via electrophilic addition under aqueous acid conditions yes no
Lion Indicate whether the use of wedge and dash bonds are required when drawing the product of using: 1-methylcyclohexene as your starting material with: A) hydroboration-oxidation yes no B) hydrogenation with a metal catalyst using protium yes no C) hydrogenation with a metal catalyst using deuterium yes no D) free radical addition of HBr yes no E) vicinal dihalide formation yes no F) electrophilic addition of HX yes no G) vicinal halohydrin formation yes no H) hydration via electrophilic addition under aqueous acid conditions yes no<\/p>\n\n\n\n

The Correct Answer and Explanation is:<\/mark><\/strong><\/p>\n\n\n\n

Here are the correct answers to whether wedge and dash bonds are required<\/strong> when drawing the product formed from 1-methylcyclohexene<\/strong> under the following reactions:<\/p>\n\n\n\n

Reaction<\/th>Wedge\/Dash Required?<\/th><\/tr><\/thead>
A) Hydroboration-oxidation<\/td>Yes<\/strong><\/td><\/tr>
B) Hydrogenation with H\u2082 and metal catalyst<\/td>Yes<\/strong><\/td><\/tr>
C) Hydrogenation with D\u2082 and metal catalyst<\/td>Yes<\/strong><\/td><\/tr>
D) Free radical addition of HBr<\/td>No<\/strong><\/td><\/tr>
E) Vicinal dihalide formation<\/td>Yes<\/strong><\/td><\/tr>
F) Electrophilic addition of HX<\/td>No<\/strong><\/td><\/tr>
G) Vicinal halohydrin formation<\/td>Yes<\/strong><\/td><\/tr>
H) Hydration via aqueous acid (electrophilic addition)<\/td>No<\/strong><\/td><\/tr><\/tbody><\/table><\/figure>\n\n\n\n
\n\n\n\n

Explanation<\/h3>\n\n\n\n

The use of wedge and dash bonds<\/strong> in organic chemistry is crucial when a reaction produces stereocenters<\/strong>\u2014carbon atoms with four different groups attached\u2014because the three-dimensional (3D) spatial arrangement<\/strong> of atoms becomes relevant.<\/p>\n\n\n\n

A) Hydroboration-oxidation<\/strong> occurs via syn addition<\/strong> of H and OH across the double bond, forming a new stereocenter. Since the OH and H add to the same face of the molecule, wedge\/dash bonds are required to show this stereochemistry.<\/p>\n\n\n\n

B) Hydrogenation with H\u2082 and a metal catalyst<\/strong> also proceeds via syn addition<\/strong> of hydrogens, potentially generating stereocenters. Therefore, wedge\/dash notation is necessary to indicate which face of the ring the hydrogens added to.<\/p>\n\n\n\n

C) Hydrogenation with D\u2082<\/strong> behaves identically to B, except deuterium (D) is used. Because D and H are distinguishable, stereochemistry is even more important<\/strong>, and wedge\/dash bonds are required.<\/p>\n\n\n\n

D) Free radical addition of HBr<\/strong> leads to non-stereoselective<\/strong> radical intermediates and planar carbocation-like species. The product is often a mixture of racemic or non-stereospecific products. Thus, wedge\/dash bonds are not required.<\/p>\n\n\n\n

E) Vicinal dihalide formation<\/strong> (e.g., Br\u2082 addition) is anti-addition<\/strong>, where halogens add to opposite faces of the double bond, creating stereocenters. Wedge\/dash bonds are required to represent the anti configuration.<\/p>\n\n\n\n

F) Electrophilic addition of HX<\/strong> leads to a planar carbocation intermediate, so the resulting product does not have a fixed stereochemistry at the new center; wedge\/dash is not required.<\/p>\n\n\n\n

G) Vicinal halohydrin formation<\/strong> is anti-addition of OH and X (e.g., Br), resulting in stereocenters. Wedge\/dash bonds are needed to show this stereochemistry.<\/p>\n\n\n\n

H) Acid-catalyzed hydration<\/strong> involves a planar carbocation intermediate and does not control stereochemistry at the new center, so wedge\/dash notation is not required.<\/p>\n\n\n\n

\"\"<\/figure>\n","protected":false},"excerpt":{"rendered":"

Lion Indicate whether the use of wedge and dash bonds are required when drawing the product of using: 1-methylcyclohexene as your starting material with: A) hydroboration-oxidation yes no B) hydrogenation with a metal catalyst using protium yes no C) hydrogenation with a metal catalyst using deuterium yes no D) free radical addition of HBr yes […]<\/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-222547","post","type-post","status-publish","format-standard","hentry","category-exams-certification"],"_links":{"self":[{"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/posts\/222547","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=222547"}],"version-history":[{"count":0,"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/posts\/222547\/revisions"}],"wp:attachment":[{"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/media?parent=222547"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/categories?post=222547"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/tags?post=222547"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}