[{"data":1,"prerenderedAt":-1},["ShallowReactive",2],{"detail-sidebar-cat-1-en-105":3,"doc-seo-572412-105":53,"doc-detail-572412-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","alkene-addition-reactions-cheat-sheet","Alkene Addition Reactions Cheat Sheet","","Alkene addition reactions overview: electrophilic halide addition (HBr via Markovnikov with carbocation formation, anti-Markovnikov only for HBr), allylic bromination using NBS with resonance-stabilized radicals, and multiple hydration routes including acid-catalyzed hydration and oxymercuration to minimize carbocation rearrangements. Coverage also includes hydroboration–oxidation for anti-Markovnikov hydroxylation with concerted syn addition, dihydroxylation (KMnO4 syn at low temperature; cleavage on heating), epoxide chemistry via nucleophilic opening rules, and halogenation mechanisms using bridged halonium ions for trans stereochemistry.",{"@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/alkene-addition-reactions-cheat-sheet/572412/",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/alkene-addition-reactions-cheat-sheet/572412.png","ImageObject",442,249,{"name":88,"@type":89},"anakgang17","Person",{"url":68,"name":91,"@type":92},"DocShare","Organization","application/pdf","2026-10-22","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},"Why does HBr addition to alkenes often follow Markovnikov’s rule?","Question",{"text":108,"@type":109},"The reaction forms a regioselective carbocation intermediate. The proton binds to the less substituted carbon to generate the more substituted, more stable carbocation, which is then attacked by bromide.","Answer",{"name":111,"@type":106,"acceptedAnswer":112},"How does oxymercuration differ from acid-catalyzed hydration?",{"text":113,"@type":109},"Oxymercuration is used to prevent carbocation rearrangements that can occur during acid-catalyzed hydration. Its mechanism proceeds through a three-membered ring intermediate.",{"name":115,"@type":106,"acceptedAnswer":116},"What determines regio- and stereochemistry in epoxide opening?",{"text":117,"@type":109},"Nucleophilic attack depends on nucleophile strength: weak nucleophiles attack the more substituted carbon, while strong nucleophiles attack the less substituted carbon.","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},572412,1792087354,{"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":9,"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":4},962090883568,"https://ap-avatar.wpscdn.com/davatar_a8503ba1806abce46bf441b54a3ca4cd","Addition of Hydrogen halide (HX)  \nRadical Addition of HBr  \nAllylic Bromination  \nAdditions to Alkenes Click here for more study guides  \n\n| The reaction goes through a regioselective formation of a carbocation. This is the Markovnikov's rule stating that the proton binds to the less substituted carbon because by doing so the more substituted/stable carbocation is formed. The halide can attack the carbocation from both faces, thus a mixture of enantiomers is produced. | | \u003Cbr> +\u003Cbr>H\u003Cbr>2o\u003Cbr>| \u003Cbr>\u003Cbr>3o carbocation Enantiomers\u003Cbr>| | |\n| --- | --- | --- | --- | --- | --- |\n|  | more stable * Notice that an alkene with a chiral center will produce a mixture of diastereomers. |  |  |  |  |\n\n\n| Only HBr works for Anti-Markovnikov addition. The reaction goes through a radical mechanism with syn and anti additions. | Br\u003Cbr>\u003Cbr>\u003Cbr>H \u003Cbr>\u003Cbr>\u003Cbr>| + | Br\u003Cbr>\u003Cbr>\u003Cbr>\u003Cbr> H | + | Br\u003Cbr>\u003Cbr> H | + | Br\u003Cbr>\u003Cbr>\u003Cbr>\u003Cbr>H \u003Cbr>\u003Cbr>\u003Cbr>| There is no stereoselectivity and a maximum number of stereoisomers can be formed. |\n| --- | --- | --- | --- | --- | --- | --- | --- | --- |\n\nBr  \n+  \nBr  \nBr  \n+  \n| NBS is used to brominate the allylic position of the double bond. So, for the regiochemistry of the bromination, you can simply identify the allylic positions and place the bromine there. | However, the reaction is not as straightforward! It involves resonance-stabilization of the allylic radicals and other regioisomers are also formed. In addition, the lack of stereochemical control makes predicting all the possible products quite difficult. You can check [https://www.chemistrysteps.com/allylic-bromination/ for more details](https://www.chemistrysteps.com/allylic-bromination/ for more details). |\n| --- | --- |\n\nAcid-catalyzed hydration  \nOxymercuration  \nH2SO4  \ndilute  \n1) Hg(OAc)2  \n2) NaBH4, NaOH  \n| Acid-catalyzed hydration follows the Markovnikov's rule. However, rearrangements are possible because of the carbocation intermediates. | Dilute H2SO4, H+ HH\u003Cbr>HOH 2o\u003Cbr>| Hhydride\u003Cbr>shift | \u003Cbr>H \u003Cbr>\u003Cbr>H 3o | H2O | H OH\u003Cbr>\u003Cbr>H\u003Cbr>| \u003Cbr>\u003Cbr>\u003Cbr>OH\u003Cbr>expected | OH\u003Cbr>\u003Cbr>observed | \u003Cbr>Syn and anti addition. |\n| --- | --- | --- | --- | --- | --- | --- | --- | --- |\n\n\n| Same product as acid-catalyzed hydration. The main reason for using Oxymercuration is preventing possible rearrangements that happen during acid-catalyzed hydration.\u003Cbr>The mechanism goes through a three-membered ring which can react with other nucleophiles such as alcohols, amines and thiols. | | 1) Hg(OAc)2, EtNH2 |  OAc\u003Cbr> Hg \u003Cbr>\u003Cbr>+ En\u003Cbr>\u003Cbr>| 1) EtNH2\u003Cbr>2) NaBH4\u003Cbr>| | + | En |\n| --- | --- | --- | --- | --- | --- | --- | --- |\n\nHydroboration-Oxidation  \nOzonolysis  \nSyn Dihydroxylation  \nSyn Dihydroxylation  \nAnti Dihydroxylation  \nHalogenation   \nHalohydrin Formation  \nBr  \nBr   \n2   \n +  \nBr    \nBr  Br2    \nHO   \nH O  \n2  \nOH  \n +  \n H  \nOH  \nH   \n| Unlike H2SO4 and Hg(OAc)2, Hydroboration-Oxidation is used for Anti-Markovnikov hydroxylation. Hydroboration is a concerted, syn addition, so the H and OH appear on the same side in the product. For better stereoselectivity, bulky dialkylboranes such as 9-BBN (R2BH general formula) are used. | |  1) BH3, THF | H  BH2\u003Cbr>\u003Cbr>+ En\u003Cbr>| 2) H2O2, NaOH | OH\u003Cbr>H \u003Cbr>\u003Cbr>\u003Cbr>+ En |\n| --- | --- | --- | --- | --- | --- |\n\nH  \nO  \n\n| Like for any other exercise, numbering the carbon chain will help a lot! | | 1) O3\u003Cbr>2) Me2S | O\u003Cbr>5\u003Cbr>6 4\u003Cbr>3 21O\u003Cbr>\u003Cbr>H\u003Cbr>| To predict the structure of starting alkene, connect the two carbons of carbonyl with a double bond: | \u003Cbr>321\u003Cbr> O\u003Cbr>4 | connect\u003Cbr>\u003Cbr>+ | \u003Cbr>O\u003Cbr>\u003Cbr>1 2 3 | 32\u003Cbr>4\u003Cbr>\u003Cbr>1\u003Cbr>\u003Cbr> 3\u003Cbr>2 1 |\n| --- | --- | --- | --- | --- | --- | --- | --- | --- |\n\n+  \n+  \nOH  \nHO  \nOH  \nHO  \n| The syn dihydroxylation with KMnO4 works only at lowered temperatures. If heat is applied, the double bond is cleaved: | \u003Cbr>KMnO4\u003Cbr>warm\u003Cbr>OH\u003Cbr>\u003Cbr>\u003Cbr>\u003Cbr>HO \u003Cbr>\u003Cbr>O\u003Cbr>  + H\u003Cbr>O\u003Cbr>O\u003Cbr>\u003Cbr>ketone\u003Cbr>+\u003Cbr>OH\u003Cbr>O\u003Cbr>acid\u003Cbr>glycol ketone aldehyde-oxidized |\n| --- | --- |\n","cbCaimy6R1hSWjDc","https://ap.wps.com/l/cbCaimy6R1hSWjDc","pdf",159044,"English","# Addition of hydrogen halides (HX)\n## Radical addition of HBr\n## Allylic bromination (NBS)\n# Additions to alkenes\n## Markovnikov vs anti-Markovnikov outcomes\n## Acid-catalyzed hydration and oxymercuration\n## Hydroboration-oxidation\n## Ozonolysis and dihydroxylation\n## Halogenation and halohydrin formation\n## Epoxide opening and stereochemical rules\n## Hydrogenation and Simmons–Smith reaction","[{\"question\":\"Why does HBr addition to alkenes often follow Markovnikov’s rule?\",\"answer\":\"The reaction forms a regioselective carbocation intermediate. The proton binds to the less substituted carbon to generate the more substituted, more stable carbocation, which is then attacked by bromide.\"},{\"question\":\"How does oxymercuration differ from acid-catalyzed hydration?\",\"answer\":\"Oxymercuration is used to prevent carbocation rearrangements that can occur during acid-catalyzed hydration. Its mechanism proceeds through a three-membered ring intermediate.\"},{\"question\":\"What determines regio- and stereochemistry in epoxide opening?\",\"answer\":\"Nucleophilic attack depends on nucleophile strength: weak nucleophiles attack the more substituted carbon, while strong nucleophiles attack the less substituted carbon.\"}]","Alkene Addition Reactions Cheat Sheet | PDF",1791927281]