{"id":9699,"date":"2024-04-03T00:45:30","date_gmt":"2024-04-03T00:45:30","guid":{"rendered":"https:\/\/chemistryscore.com\/?page_id=9699---cd1278fc-8ddb-4cfa-9052-2987c3219644"},"modified":"2024-04-03T00:45:30","modified_gmt":"2024-04-03T00:45:30","slug":"oxymercuration","status":"publish","type":"post","link":"https:\/\/chemistryscore.com\/oxymercuration\/","title":{"rendered":"Oxymercuration"},"content":{"rendered":"\t\t<div data-elementor-type=\"wp-page\" data-elementor-id=\"9699\" class=\"elementor elementor-9699\">\n\t\t\t\t\t\t<section class=\"elementor-section elementor-top-section elementor-element elementor-element-b2f591f elementor-section-boxed elementor-section-height-default elementor-section-height-default\" data-id=\"b2f591f\" data-element_type=\"section\">\n\t\t\t\t\t\t<div class=\"elementor-container elementor-column-gap-default\">\n\t\t\t\t\t<div class=\"elementor-column elementor-col-100 elementor-top-column elementor-element elementor-element-32117cd\" data-id=\"32117cd\" data-element_type=\"column\">\n\t\t\t<div class=\"elementor-widget-wrap elementor-element-populated\">\n\t\t\t\t\t\t<div class=\"elementor-element elementor-element-335f776 elementor-widget elementor-widget-text-editor\" data-id=\"335f776\" data-element_type=\"widget\" data-widget_type=\"text-editor.default\">\n\t\t\t\t<div class=\"elementor-widget-container\">\n\t\t\t\t\t\t\t<h1>Oxymercuration<\/h1><h2>Oxymercuration Definition:<\/h2><p><strong>Alkynes<\/strong>\u00a0treated with\u00a0<strong>mercury<\/strong>\u00a0(usually HgSO<sub>4<\/sub>) and\u00a0<strong>water<\/strong>\u00a0will be hydrated to give\u00a0<strong>ketones<\/strong>, via an\u00a0<strong>enol<\/strong>\u00a0intermediate.<\/p><p><img fetchpriority=\"high\" decoding=\"async\" class=\"aligncenter size-full wp-image-9701\" src=\"https:\/\/chemistryscore.com\/wp-content\/uploads\/2019\/11\/Oxymercuration1-1024x305.png\" alt=\"\" width=\"1024\" height=\"305\" srcset=\"https:\/\/chemistryscore.com\/wp-content\/uploads\/2019\/11\/Oxymercuration1-1024x305.png 1024w, https:\/\/chemistryscore.com\/wp-content\/uploads\/2019\/11\/Oxymercuration1-1024x305-300x89.png 300w, https:\/\/chemistryscore.com\/wp-content\/uploads\/2019\/11\/Oxymercuration1-1024x305-768x229.png 768w\" sizes=\"(max-width: 1024px) 100vw, 1024px\" \/><\/p><h2>Oxymercuration Explained:<\/h2><p><strong>Hydration<\/strong>\u00a0of alkynes is similar to the acid-catalyst addition of the water to alkenes, but the reaction is slower than the corresponding reaction with alkenes. As we have said, a major reason for this difference in reactivity is the substantially higher energy of the vinylic carbocation intermediate that is formed when an alkyne is protonated. The rate of alkyne hydration is markedly enhanced in the presence of\u00a0<strong>strong acid<\/strong>\u00a0or\u00a0<strong>Hg<sup>2+<\/sup>catalyst<\/strong>\u00a0(usually mercuric sulfate, HgSO<sub>4<\/sub>). Under these conditions, the elements of water (H<sub>2<\/sub>O) are added to a triple bond and\u00a0<strong>enol<\/strong>\u00a0is obtained. Enol contains both a carbon-carbon double bond of alkenes and a hydroxyl group of the alcohol.<\/p><p><img decoding=\"async\" class=\"aligncenter size-full wp-image-9703\" src=\"https:\/\/chemistryscore.com\/wp-content\/uploads\/2019\/11\/Oxymercuration2-300x263.png\" alt=\"\" width=\"300\" height=\"263\" \/><\/p><p>This intermediate cannot be isolated because it is very unstable and rapidly converted into a\u00a0<strong>ketone<\/strong>. This conversion is called\u00a0<strong>keto-enol tautomerization<\/strong>\u00a0and can be catalyzed both by acid and base. Now, we will see the acid-catalyzed conversion of an enol to a ketone occur via two steps:<\/p><p><strong>STEP 1.<\/strong>\u00a0Protonation of the double bond of the enol with acid adds H+ to form a resonance-stabilized carbocation.<\/p><p><img decoding=\"async\" class=\"aligncenter size-full wp-image-9705\" src=\"https:\/\/chemistryscore.com\/wp-content\/uploads\/2019\/11\/Oxymercuration3-1024x373.png\" alt=\"\" width=\"1024\" height=\"373\" srcset=\"https:\/\/chemistryscore.com\/wp-content\/uploads\/2019\/11\/Oxymercuration3-1024x373.png 1024w, https:\/\/chemistryscore.com\/wp-content\/uploads\/2019\/11\/Oxymercuration3-1024x373-300x109.png 300w, https:\/\/chemistryscore.com\/wp-content\/uploads\/2019\/11\/Oxymercuration3-1024x373-768x280.png 768w\" sizes=\"(max-width: 1024px) 100vw, 1024px\" \/><\/p><p><br \/><b>STEP 2<\/b>. Loss of the proton forms the carbonyl group.<\/p><p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-full wp-image-9707\" src=\"https:\/\/chemistryscore.com\/wp-content\/uploads\/2019\/11\/Oxymercuration4-768x247.png\" alt=\"\" width=\"768\" height=\"247\" srcset=\"https:\/\/chemistryscore.com\/wp-content\/uploads\/2019\/11\/Oxymercuration4-768x247.png 768w, https:\/\/chemistryscore.com\/wp-content\/uploads\/2019\/11\/Oxymercuration4-768x247-300x96.png 300w\" sizes=\"(max-width: 768px) 100vw, 768px\" \/><br \/>The enol is said to <b>tautomerize <\/b>to the carbonyl compound, and the two new species are called <b>tautomers <\/b>which means that they are constitutional isomers that rapidly that rapidly interconvert via the migration of a proton.<\/p>\t\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t\t<\/div>\n\t\t<\/div>\n\t\t\t\t\t<\/div>\n\t\t<\/section>\n\t\t\t\t<\/div>\n\t\t","protected":false},"excerpt":{"rendered":"<p>Oxymercuration Oxymercuration Definition: Alkynes&nbsp;treated with&nbsp;mercury&nbsp;(usually HgSO4) and&nbsp;water&nbsp;will be hydrated to give&nbsp;ketones, via an&nbsp;enol&nbsp;intermediate. Oxymercuration Explained: Hydration&nbsp;of alkynes is similar to the acid-catalyst addition of the water to alkenes, but the reaction is slower than the corresponding reaction with alkenes. As we have said, a major reason for this difference in reactivity is the substantially higher [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"elementor_header_footer","format":"standard","meta":{"ocean_post_layout":"","ocean_both_sidebars_style":"","ocean_both_sidebars_content_width":0,"ocean_both_sidebars_sidebars_width":0,"ocean_sidebar":"0","ocean_second_sidebar":"0","ocean_disable_margins":"enable","ocean_add_body_class":"","ocean_shortcode_before_top_bar":"","ocean_shortcode_after_top_bar":"","ocean_shortcode_before_header":"","ocean_shortcode_after_header":"","ocean_has_shortcode":"","ocean_shortcode_after_title":"","ocean_shortcode_before_footer_widgets":"","ocean_shortcode_after_footer_widgets":"","ocean_shortcode_before_footer_bottom":"","ocean_shortcode_after_footer_bottom":"","ocean_display_top_bar":"default","ocean_display_header":"default","ocean_header_style":"","ocean_center_header_left_menu":"0","ocean_custom_header_template":"0","ocean_custom_logo":0,"ocean_custom_retina_logo":0,"ocean_custom_logo_max_width":0,"ocean_custom_logo_tablet_max_width":0,"ocean_custom_logo_mobile_max_width":0,"ocean_custom_logo_max_height":0,"ocean_custom_logo_tablet_max_height":0,"ocean_custom_logo_mobile_max_height":0,"ocean_header_custom_menu":"0","ocean_menu_typo_font_family":"0","ocean_menu_typo_font_subset":"","ocean_menu_typo_font_size":0,"ocean_menu_typo_font_size_tablet":0,"ocean_menu_typo_font_size_mobile":0,"ocean_menu_typo_font_size_unit":"px","ocean_menu_typo_font_weight":"","ocean_menu_typo_font_weight_tablet":"","ocean_menu_typo_font_weight_mobile":"","ocean_menu_typo_transform":"","ocean_menu_typo_transform_tablet":"","ocean_menu_typo_transform_mobile":"","ocean_menu_typo_line_height":0,"ocean_menu_typo_line_height_tablet":0,"ocean_menu_typo_line_height_mobile":0,"ocean_menu_typo_line_height_unit":"","ocean_menu_typo_spacing":0,"ocean_menu_typo_spacing_tablet":0,"ocean_menu_typo_spacing_mobile":0,"ocean_menu_typo_spacing_unit":"","ocean_menu_link_color":"","ocean_menu_link_color_hover":"","ocean_menu_link_color_active":"","ocean_menu_link_background":"","ocean_menu_link_hover_background":"","ocean_menu_link_active_background":"","ocean_menu_social_links_bg":"","ocean_menu_social_hover_links_bg":"","ocean_menu_social_links_color":"","ocean_menu_social_hover_links_color":"","ocean_disable_title":"default","ocean_disable_heading":"on","ocean_post_title":"","ocean_post_subheading":"","ocean_post_title_style":"","ocean_post_title_background_color":"","ocean_post_title_background":0,"ocean_post_title_bg_image_position":"","ocean_post_title_bg_image_attachment":"","ocean_post_title_bg_image_repeat":"","ocean_post_title_bg_image_size":"","ocean_post_title_height":0,"ocean_post_title_bg_overlay":0.5,"ocean_post_title_bg_overlay_color":"","ocean_disable_breadcrumbs":"default","ocean_breadcrumbs_color":"","ocean_breadcrumbs_separator_color":"","ocean_breadcrumbs_links_color":"","ocean_breadcrumbs_links_hover_color":"","ocean_display_footer_widgets":"default","ocean_display_footer_bottom":"default","ocean_custom_footer_template":"0","_jetpack_memberships_contains_paid_content":false,"ocean_post_oembed":"","ocean_post_self_hosted_media":"","ocean_post_video_embed":"","ocean_link_format":"","ocean_link_format_target":"self","ocean_quote_format":"","ocean_quote_format_link":"post","ocean_gallery_link_images":"off","ocean_gallery_id":[],"footnotes":""},"categories":[5636],"tags":[],"jetpack_sharing_enabled":true,"jetpack_featured_media_url":"","yoast_head":"<!-- This site is optimized with the Yoast SEO Premium plugin v14.9 - https:\/\/yoast.com\/wordpress\/plugins\/seo\/ -->\n<title>Oxymercuration - ChemistryScore<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/chemistryscore.com\/oxymercuration\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Oxymercuration - ChemistryScore\" \/>\n<meta property=\"og:description\" content=\"Oxymercuration Oxymercuration Definition: Alkynes&nbsp;treated with&nbsp;mercury&nbsp;(usually HgSO4) and&nbsp;water&nbsp;will be hydrated to give&nbsp;ketones, via an&nbsp;enol&nbsp;intermediate. 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