{"id":8738,"date":"2024-01-12T04:28:17","date_gmt":"2024-01-12T04:28:17","guid":{"rendered":"https:\/\/chemistryscore.com\/?page_id=8738---f4154d38-3df8-4888-83f2-3c1cda7929c2"},"modified":"2024-01-12T04:28:17","modified_gmt":"2024-01-12T04:28:17","slug":"alkyl-chloride-formation-hcl","status":"publish","type":"post","link":"https:\/\/chemistryscore.com\/alkyl-chloride-formation-hcl\/","title":{"rendered":"Alkyl chloride formation [HCl]"},"content":{"rendered":"\t\t<div data-elementor-type=\"wp-page\" data-elementor-id=\"8738\" class=\"elementor elementor-8738\">\n\t\t\t\t\t\t<section class=\"elementor-section elementor-top-section elementor-element elementor-element-fd075b3 elementor-section-boxed elementor-section-height-default elementor-section-height-default\" data-id=\"fd075b3\" 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-5923ea3\" data-id=\"5923ea3\" 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-0e3d095 elementor-widget elementor-widget-text-editor\" data-id=\"0e3d095\" 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>Alkyl chloride formation [HCl]<\/h1><h2>Alkyl chloride formation (HCl) Definition:<\/h2><p>Treatment of <b>tertiary alcohols<\/b> with <b>HCl <\/b>leads to the formation of <b>tertiary alkyl chlorides<\/b>.<\/p><p><img fetchpriority=\"high\" decoding=\"async\" class=\"aligncenter size-full wp-image-8741\" src=\"https:\/\/chemistryscore.com\/wp-content\/uploads\/2019\/11\/Alkyl-chloride-formation-HCl1-768x284.png\" alt=\"\" width=\"768\" height=\"284\" srcset=\"https:\/\/chemistryscore.com\/wp-content\/uploads\/2019\/11\/Alkyl-chloride-formation-HCl1-768x284.png 768w, https:\/\/chemistryscore.com\/wp-content\/uploads\/2019\/11\/Alkyl-chloride-formation-HCl1-768x284-300x111.png 300w\" sizes=\"(max-width: 768px) 100vw, 768px\" \/><\/p><h2>Alkyl chloride formation (HCl) Explained:<\/h2><p>The order of reactivity of alcohol is tertiary &gt; secondary &gt; primary &gt; methyl which is opposite of reactivity in S<sub>N<\/sub>2 substitution. Methanol and primary alcohols will proceed via an S<sub>N<\/sub>2 mechanism since these have highly unfavorable carbocations. Secondary alcohols can also be subject to both an S<sub>N<\/sub>1 or S<sub>N<\/sub>2 depending on the reaction conditions. Reaction with tertiary alcohol usually proceeds via an S<sub>N<\/sub>1 mechanism where the carbocation is obtained as an intermediate which can undergo rearrangement.<\/p><p><b>STEP 1<\/b>. The alcohol is protonated to gives its conjugate acid which is a good leaving group. This is very fast and reversible step.<\/p><p><img decoding=\"async\" class=\"aligncenter size-full wp-image-8742\" src=\"https:\/\/chemistryscore.com\/wp-content\/uploads\/2019\/11\/Alkyl-chloride-formation-HCl2-1-768x397.png\" alt=\"\" width=\"768\" height=\"397\" srcset=\"https:\/\/chemistryscore.com\/wp-content\/uploads\/2019\/11\/Alkyl-chloride-formation-HCl2-1-768x397.png 768w, https:\/\/chemistryscore.com\/wp-content\/uploads\/2019\/11\/Alkyl-chloride-formation-HCl2-1-768x397-300x155.png 300w\" sizes=\"(max-width: 768px) 100vw, 768px\" \/><\/p><p><b>STEP 2<\/b>. Cleavage of the C-O bond allows the loss of the good leaving group, a neutral water molecule, to give a carbocation. Bond breaking is endothermic reaction so this step is the rate-determining step.<\/p><p><img decoding=\"async\" class=\"aligncenter size-full wp-image-8743\" src=\"https:\/\/chemistryscore.com\/wp-content\/uploads\/2019\/11\/Alkyl-chloride-formation-HCl3-1-768x344.png\" alt=\"\" width=\"768\" height=\"344\" srcset=\"https:\/\/chemistryscore.com\/wp-content\/uploads\/2019\/11\/Alkyl-chloride-formation-HCl3-1-768x344.png 768w, https:\/\/chemistryscore.com\/wp-content\/uploads\/2019\/11\/Alkyl-chloride-formation-HCl3-1-768x344-300x134.png 300w\" sizes=\"(max-width: 768px) 100vw, 768px\" \/><\/p><p><b>STEP 3<\/b>. Nucleophilic attack of bromide ion to the electrophilic carbocation and alkyl chloride formation.<\/p><p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-full wp-image-8744\" src=\"https:\/\/chemistryscore.com\/wp-content\/uploads\/2019\/11\/Alkyl-chloride-formation-HCl4-768x327.png\" alt=\"\" width=\"768\" height=\"327\" srcset=\"https:\/\/chemistryscore.com\/wp-content\/uploads\/2019\/11\/Alkyl-chloride-formation-HCl4-768x327.png 768w, https:\/\/chemistryscore.com\/wp-content\/uploads\/2019\/11\/Alkyl-chloride-formation-HCl4-768x327-300x128.png 300w\" sizes=\"(max-width: 768px) 100vw, 768px\" \/><\/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>Alkyl chloride formation [HCl] Alkyl chloride formation (HCl) Definition: Treatment of tertiary alcohols with HCl leads to the formation of tertiary alkyl chlorides. Alkyl chloride formation (HCl) Explained: The order of reactivity of alcohol is tertiary &gt; secondary &gt; primary &gt; methyl which is opposite of reactivity in SN2 substitution. Methanol and primary alcohols will [&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":[5624],"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>Alkyl chloride formation [HCl] - 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\/alkyl-chloride-formation-hcl\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Alkyl chloride formation [HCl] - ChemistryScore\" \/>\n<meta property=\"og:description\" content=\"Alkyl chloride formation [HCl] Alkyl chloride formation (HCl) Definition: Treatment of tertiary alcohols with HCl leads to the formation of tertiary alkyl chlorides. 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