[{"data":1,"prerenderedAt":-1},["ShallowReactive",2],{"detail-sidebar-cat-1-en-105":3,"doc-seo-572414-105":53,"doc-detail-572414-en":126},{"code":4,"msg":5,"data":6},0,"success",[7,14,19,24,29,34,39,44,49],{"id":8,"doc_module":9,"doc_module_name":10,"category_name":11,"show_sort_weight":12,"slug":13},11,1,"Template","Presentations",90,"presentations",{"id":15,"doc_module":9,"doc_module_name":10,"category_name":16,"show_sort_weight":17,"slug":18},12,"Resumes",80,"resumes",{"id":20,"doc_module":9,"doc_module_name":10,"category_name":21,"show_sort_weight":22,"slug":23},14,"Invoices",70,"invoices",{"id":25,"doc_module":9,"doc_module_name":10,"category_name":26,"show_sort_weight":27,"slug":28},15,"Posters",60,"posters",{"id":30,"doc_module":9,"doc_module_name":10,"category_name":31,"show_sort_weight":32,"slug":33},16,"Social Media",50,"social-media",{"id":35,"doc_module":9,"doc_module_name":10,"category_name":36,"show_sort_weight":37,"slug":38},17,"Forms",40,"forms",{"id":40,"doc_module":9,"doc_module_name":10,"category_name":41,"show_sort_weight":42,"slug":43},18,"Letters",30,"letters",{"id":45,"doc_module":9,"doc_module_name":10,"category_name":46,"show_sort_weight":47,"slug":48},21,"Paper Templates",5,"papers-templates",{"id":50,"doc_module":9,"doc_module_name":10,"category_name":51,"show_sort_weight":4,"slug":52},158,"General","general-158",{"code":4,"msg":54,"data":55},"ok",{"site_id":56,"language":57,"slug":58,"title":59,"keywords":60,"description":61,"schema_data":62,"social_meta":119,"head_meta":121,"extra_data":123,"updated_unix":125},105,"en","reactions-of-alkenes-summary-addition-stereochemistry-and-intermediates-key-rules","Reactions of Alkenes - Summary - Addition stereochemistry and intermediates - key rules","","Concise summary of alkene reactions focusing on addition mechanisms, intermediates, and stereochemical outcomes. Covers how Markovnikov versus anti-Markovnikov behavior relates to the most stable carbocation or radical intermediate, and how rearrangements are evaluated. Provides stereochemistry rules for optically inactive versus active reactants, guidance for predicting maximum stereoisomers from syn/anti additions, and a decision framework for determining intermediate type: carbocation, radical, 3-membered ring, or none/cyclic concerted. Includes example reagent-to-product mappings for diols, epoxides, and other products.",{"@graph":63,"@context":118},[64,80,101],{"@type":65,"itemListElement":66},"BreadcrumbList",[67,71,74,77],{"item":68,"name":69,"@type":70,"position":9},"https://docshare.wps.com","Home","ListItem",{"item":72,"name":10,"@type":70,"position":73},"https://docshare.wps.com/template/",2,{"item":75,"name":51,"@type":70,"position":76},"https://docshare.wps.com/template/general/",3,{"item":78,"name":59,"@type":70,"position":79},"https://docshare.wps.com/template/reactions-of-alkenes-summary-addition-stereochemistry-and-intermediates-key-rules/572414/",4,{"url":78,"name":59,"@type":81,"image":82,"author":87,"headline":59,"publisher":90,"fileFormat":93,"inLanguage":57,"description":61,"dateModified":94,"datePublished":95,"encodingFormat":93,"isAccessibleForFree":96,"interactionStatistic":97},"DigitalDocument",{"url":83,"@type":84,"width":85,"height":86},"https://docshare.wps.com/thumbnails/reactions-of-alkenes-summary-addition-stereochemistry-and-intermediates-key-rules/572414.png","ImageObject",442,249,{"name":88,"@type":89},"pixelkiddo","Person",{"url":68,"name":91,"@type":92},"DocShare","Organization","application/pdf","2026-10-23","2026-10-13",true,{"@type":98,"interactionType":99,"userInteractionCount":79},"InteractionCounter",{"@type":100},"ViewAction",{"@type":102,"mainEntity":103},"FAQPage",[104,110,114],{"name":105,"@type":106,"acceptedAnswer":107},"How is regiochemistry (Markovnikov vs anti-Markovnikov) determined for alkene additions?","Question",{"text":108,"@type":109},"The reaction proceeds through the pathway of the most stable intermediate. Greater electron-deficient carbon substitution on a carbocation or radical increases intermediate stability, which dictates Markovnikov-like versus anti-Markovnikov-like outcomes.","Answer",{"name":111,"@type":106,"acceptedAnswer":112},"What stereochemical outcomes occur when reactants are optically inactive versus optically active?",{"text":113,"@type":109},"Optically inactive (achiral) reactants give optically inactive products (racemic or meso). Optically active (chiral) reactants yield optically active products, including unequal enantiomer mixtures, unequal diastereomer mixtures, or a single enantiomer depending on the pathway.",{"name":115,"@type":106,"acceptedAnswer":116},"How do you predict the type of intermediate involved in an alkene reaction?",{"text":117,"@type":109},"Use the electrophile characteristics: carbocation when the electrophile is H with no lone pair to share; radical when an initiator with a weak bond plus heat or light is present; 3-membered ring when the electrophile has a lone pair to share; none/cyclic concerted when the electrophile can both accept and donate electrons at the same time.","https://schema.org",{"og:url":78,"og:type":120,"og:title":59,"og:site_name":91,"og:description":61},"article",{"robots":122,"canonical":78},"index,follow",{"doc_id":124,"site_id":56},572414,1792087024,{"code":4,"msg":5,"data":127},{"doc_id":124,"user_id":128,"nickname":88,"user_avatar":129,"doc_module":9,"category_id":50,"category_name":51,"doc_title":59,"doc_description":61,"doc_content":130,"file_id":131,"file_url":132,"file_type":133,"file_size":134,"view_count":79,"is_deleted":4,"is_public":9,"is_downloadable":9,"audit_status":9,"page_count":79,"language":135,"language_code":57,"site_id":56,"html_lang":57,"table_of_contents":136,"faqs":137,"seo_title":138,"seo_description":61,"update_tm":139,"read_time":73},962090883892,"https://ap-avatar.wpscdn.com/avatar/e00115db34f3e0f11b?x-image-process=image/resize,m_fixed,w_180,h_180&k=1790152879550218658","Reactions of Alkenes: Summary  \nIntermediate:  Carbocation Radical 3-Membered Ring None or Cyclic (concerted)  \nRegiochemisty: Markovnikov* Anti-Markovnikov* Markovnikov-like N/A  \nAddition: Syn & Anti Syn & Anti Anti Syn  \nRearrangements? yes no no no  \n*the reaction goes through the pathway of the most stable intermediate;  \nthe more substituents on an electron deficient carbon (carbocation or radical), the greater its stability  \nStereochemistry:  \n• If the reactants are optically inactive (achiral), the products will be optically inactive (achiral , racemic or meso)  \n• If the reactants are optically active (chiral), the products will be optically active (unequal mixture of enantiomers , unequal mixture of diastereomers , or 1 enantiomer)  \n• Use 2 n of the product to predict the maximum number of stereoisomers  \n(if just anti or just syn addition, divide the maximum number of stereoisomers by 2)  \nPredicting the type of intermediate:  \n• Carbocation-H is the electrophile (no lone pair to share with the empty p orbital)  \n• Radical-an initiator with a weak bond (ex. ROOR) and an energy source (heat or light) is present  \n• 3-Membered Ring-the electrophile has a lone pair of electrons available to share with the empty p orbital  \n• None or Cyclic-the electrophile can both accept and donate electrons at the same time  \n| | 1. Hg(OAc)2, MeOH\u003Cbr>2. NaBH4 | \u003Cbr>\u003Cbr>H3C\u003Cbr>3\u003Cbr>\u003Cbr>OCH | Ether | 3-membered ring | anti | Markovnikov-like |\n| --- | --- | --- | --- | --- | --- | --- |\n|   CHX3, KOH \u003Cbr>\u003Cbr>CH3 |  | \u003Cbr>\u003Cbr>\u003Cbr>C\u003Cbr>\u003Cbr>X\u003Cbr>X\u003Cbr>3\u003Cbr>CH | Cyclopropane | None\u003Cbr>(concerted) | syn | N/A |\n| |  CH2I2 , Zn(Cu)  | \u003Cbr>\u003Cbr>\u003Cbr>C\u003Cbr>\u003Cbr>H\u003Cbr>H\u003Cbr>3\u003Cbr>CH | Cyclopropane | None\u003Cbr>(concerted) | syn | N/A |\n| | \u003Cbr>\u003Cbr>H2 /C\u003Cbr>( 2 2)\u003Cbr>3\u003Cbr>\u003Cbr>, Pd\u003Cbr>or H , PtO\u003Cbr>CH |  | Alkane | Heterogeneous | syn | N/A |\n| |  RCO3 H  | \u003Cbr>\u003Cbr>3\u003Cbr>O\u003Cbr>\u003Cbr>CH | Epoxide | None\u003Cbr>(concerted) | syn | N/A |\n| \u003Cbr>CH3 O\u003Cbr>|  | OH\u003Cbr>HO CH3 | trans-1,2-diol | 3-membered ring | anti | N/A |\n| \u003Cbr>\u003Cbr>\u003Cbr>O\u003Cbr>CH3 |  | \u003Cbr>~~ ~~  CH3 HO\u003Cbr>OH | trans-1,2-diol | None\u003Cbr>(concerted) | anti | N/A |\n\n\n| CH3\u003Cbr>\u003Cbr>| 1. OsO4\u003Cbr>\u003Cbr>2. NaHSO3 , H2O (or H2O2)\u003Cbr>CH3 HO OH\u003Cbr>|  | cis-1,2-diol | Cyclic\u003Cbr>(concerted) | syn |\n| --- | --- | --- | --- | --- | --- |\n| CH3\u003Cbr>\u003Cbr>| KMnO4 (cold, dilute)\u003Cbr>-OH, H2O | CH3\u003Cbr>HO OH\u003Cbr>\u003Cbr>\u003Cbr>\u003Cbr>| cis-1,2-diol | Cyclic\u003Cbr>(concerted) | syn |\n| CH3 HO OH\u003Cbr>\u003Cbr>| HIO4 , H2O\u003Cbr>| H CH3 O O\u003Cbr>| Aldehydesand Ketones | Cyclic\u003Cbr>(concerted) | syn |\n| \u003Cbr>CH3\u003Cbr>| 1. O3\u003Cbr>\u003Cbr>2. Zn(H3O+) or (CH3)2S | HCH3\u003Cbr>O O | Aldehydesand Ketones | Cyclic\u003Cbr>(concerted) | syn |\n| \u003Cbr>\u003Cbr>CH3\u003Cbr>| 1. O3\u003Cbr>\u003Cbr>2. H2O2 | HO CH3 O O | Carboxylic acids and Ketones | Cyclic\u003Cbr>(concerted) | syn |\n| \u003Cbr>\u003Cbr>CH3 | KMnO4 (hot, conc'd)\u003Cbr>\u003Cbr>H3O+, H2O | HO CH3 O O | Carboxylic acids and Ketones | Cyclic\u003Cbr>(concerted) | syn |","cbCais1zWfIsr4jY","https://ap.wps.com/l/cbCais1zWfIsr4jY","pdf",125672,"English","# Reactions of Alkenes - Summary\n## Mechanism and Regiochemistry\n## Addition Stereochemistry\n## Predicting the Type of Intermediate\n## Reagent-to-Product Examples","[{\"question\":\"How is regiochemistry (Markovnikov vs anti-Markovnikov) determined for alkene additions?\",\"answer\":\"The reaction proceeds through the pathway of the most stable intermediate. Greater electron-deficient carbon substitution on a carbocation or radical increases intermediate stability, which dictates Markovnikov-like versus anti-Markovnikov-like outcomes.\"},{\"question\":\"What stereochemical outcomes occur when reactants are optically inactive versus optically active?\",\"answer\":\"Optically inactive (achiral) reactants give optically inactive products (racemic or meso). Optically active (chiral) reactants yield optically active products, including unequal enantiomer mixtures, unequal diastereomer mixtures, or a single enantiomer depending on the pathway.\"},{\"question\":\"How do you predict the type of intermediate involved in an alkene reaction?\",\"answer\":\"Use the electrophile characteristics: carbocation when the electrophile is H with no lone pair to share; radical when an initiator with a weak bond plus heat or light is present; 3-membered ring when the electrophile has a lone pair to share; none/cyclic concerted when the electrophile can both accept and donate electrons at the same time.\"}]","Reactions of Alkenes - Summary - Addition stereochemistry and intermediates - key rules | PDF",1791927282]