[{"data":1,"prerenderedAt":-1},["ShallowReactive",2],{"detail-sidebar-cat-1-en-105":3,"doc-seo-572417-105":53,"doc-detail-572417-en":130},{"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":123,"head_meta":125,"extra_data":127,"updated_unix":129},105,"en","reactions-of-alkenes-electrophilic-addition-orientation-and-markovnikov-radical-addition-hydration","Reactions of Alkenes - Electrophilic Addition - Orientation and Markovnikov, Radical Addition, Hydration","","Reactions of alkenes explains how double bonds undergo addition reactions to form new single-bond products, emphasizing electrophilic addition as the most common pathway. It describes carbocation formation, nucleophilic attack, and how Markovnikov orientation arises from the most stable intermediate. The document also covers the peroxide effect enabling anti-Markovnikov outcomes via free-radical mechanisms, and details alkene hydration to alcohols, including microscopic reversibility and Markovnikov regiospecificity. Practical limitations of dilute acid hydration are noted alongside indirect methods such as sulfuric-acid addition/hydrolysis and oxymercuration-demercuration.",{"@graph":63,"@context":122},[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-electrophilic-addition-orientation-and-markovnikov-radical-addition-hydration/572417/",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-electrophilic-addition-orientation-and-markovnikov-radical-addition-hydration/572417.png","ImageObject",442,249,{"name":88,"@type":89},"MrHarris58","Person",{"url":68,"name":91,"@type":92},"DocShare","Organization","application/pdf","2026-10-20","2026-10-13",true,{"@type":98,"interactionType":99,"userInteractionCount":76},"InteractionCounter",{"@type":100},"ViewAction",{"@type":102,"mainEntity":103},"FAQPage",[104,110,114,118],{"name":105,"@type":106,"acceptedAnswer":107},"What makes electrophilic addition of alkenes so common?","Question",{"text":108,"@type":109},"Electrophilic addition proceeds by electrophile attack on the alkene, generating a carbocation that is then attacked to form the overall product. The document states electrophilic addition is probably the most common reaction of alkenes.","Answer",{"name":111,"@type":106,"acceptedAnswer":112},"Why does Markovnikov orientation occur in HBr addition?",{"text":113,"@type":109},"Protonation occurs at the least substituted end, producing a carbocation at the more substituted (and therefore more stable) end. The more stable intermediate leads to the observed product.",{"name":115,"@type":106,"acceptedAnswer":116},"How do free radical conditions produce anti-Markovnikov products?",{"text":117,"@type":109},"In the presence of free radical initiators, the mechanism shifts from electrophilic addition to free radical addition using bromine radicals. The reaction forms intermediates that favor the more stable radical, reversing the regiochemistry (the peroxide effect).",{"name":119,"@type":106,"acceptedAnswer":120},"How does hydration of alkenes give alcohols and what is its regiochemistry?",{"text":121,"@type":109},"Hydration is the reverse of dehydration and follows microscopic reversibility in the opposite order. Protonation generates a carbocation attacked by water, then deprotonation yields alcohols, with Markovnikov orientation due to the carbocation stability and where the proton and hydroxyl add.","https://schema.org",{"og:url":78,"og:type":124,"og:title":59,"og:site_name":91,"og:description":61},"article",{"robots":126,"canonical":78},"index,follow",{"doc_id":128,"site_id":56},572417,1792230048,{"code":4,"msg":5,"data":131},{"doc_id":128,"user_id":132,"nickname":88,"user_avatar":133,"doc_module":9,"category_id":50,"category_name":51,"doc_title":59,"doc_description":61,"doc_content":134,"file_id":135,"file_url":136,"file_type":137,"file_size":138,"view_count":76,"is_deleted":4,"is_public":9,"is_downloadable":9,"audit_status":9,"page_count":139,"language":140,"language_code":57,"site_id":56,"html_lang":57,"table_of_contents":141,"faqs":142,"seo_title":143,"seo_description":61,"update_tm":144,"read_time":15},687212988360,"https://ap-avatar.wpscdn.com/davatar_276721f389ce27ea32af1340a28f341c","Reactions of Alkenes  \nSince 􀁖 bonds are stronger than 􀁓 bonds, double bonds tend to react to convert the double bond into 􀁖 bonds  \nThis is an addition reaction. (Other types of reaction have been substitution and elimination) .  \nAddition reactions are typically exothermic.  \nElectrophilic Addition  \nThe 􀁓 bond is localized above and below the C-C 􀁖 bond. The 􀁓 electrons are relatively far away from the nuclei and are therefore loosely bound.  \nAn electrophile will attract those electrons, and can pull them away to form a new bond. This leaves one carbon with only 3 bonds and a +ve charge (carbocation) .  \nThe double bond acts as a nucleophile (attacks the electrophile) .  \nIn most cases, the cation produced will react with another nucleophile to produce the final overall electrophilic addition product.  \nElectrophilic addition is probably the most common reaction of alkenes.  \nConsider the electrophilic addition of H-Br to but-2-ene:  \nThe alkene abstracts a proton from the HBr, and a carbocation and bromide ion are generated.  \nThe bromide ion quickly attacks the cationic center and yields the final product.  \nIn the final product, H-Br has been added across the double bond.  \nOrientation of Addition  \nConsider the addition of H-Br to 2-methylbut-2-ene:  \nThere are two possible products arising from the two different ways of adding H-Br across the double bond. But only one is observed.  \nThe observed product is the one resulting from the more stable carbocation intermediate.  \nTertiary carbocations are more stable than secondary.  \nThe protonation occurs at the least highly substituted end so that the cation produced is at the most highly substituted end (and therefore more stable) .  \nMarkovnikov’s Rule: The addition of a proton acid to the double bond of an alkene results in a product with the acid hydrogen bound to the carbon atom that already has the greater number of hydrogens attached.  \n(More generally: In an electrophilic addition to an alkene, the electrophile adds in such a way that it generates the most stable intermediate) .  \nReactions that give such products are said to have Markovnikov orientation, and are Markovnikov products.  \nThe electrophilic addition of HBr is said to be regiospecific, since it only gives one orientation of addition.  \n(HCl and HI perform analogous electrophilic addition reactions) .  \nFree Radical addition to Alkenes  \nIt is possible to obtain anti-Markovnikov products when HBr is added to alkenes in the presence of free radical initiators.  \nThe free radical initiators change the mechanism of addition from electrophilic addition to free radical addition.  \nThis change of mechanism gives rise to the opposite regiochemistry.  \nInitiation:  \nThe oxygen-oxygen bond is weak, and is easily homolytically cleaved to generate two alkoxy radicals, which in turn abstract hydrogen to generate bromine radicals.  \nPropagation:  \nThe bromine radical is electron deficient and electrophilic. The radical adds to the double bond, generating a carbon centered radical.  \nThis radical then abstracts hydrogen from a molecule of H-Br, giving the product, and another bromine radical.(Chain process) .  \nThe orientation of this reaction is anti Markovnikov.  \nThe reversal of regiochemistry through the use of peroxides is called the peroxide effect.  \nTo explain the different regiochemistry, we must look at the intermediates:  \nThe electrophile adds to the least substituted end just like before, but this time the electrophile is a bromine radical (not a proton) . This generates an intermediate radical.  \nTertiary radicals are more stable than secondary radicals.  \nThe reaction goes through the most stable intermediate. (It still follows the expanded Markovnikov rules, but the orientation is anti Markovnikov) .  \n(Radical additions do not proceed with HCl or HI, only HBr) .  \nAddition of Water  \nAlkenes can be converted to alcohols.  \nIt is the reverse reaction of the dehydration of alcohols to give alkenes.  \nT","cbCaieiWf57F4bl5","https://ap.wps.com/l/cbCaieiWf57F4bl5","pdf",2354244,35,"English","# Electrophilic addition\n## Carbocation formation and mechanism\n## Markovnikov orientation and regiospecificity\n# Free radical addition\n## Anti-Markovnikov regiochemistry and peroxide effect\n# Addition of water (hydration)\n## Microscopic reversibility and Markovnikov outcomes\n## Indirect hydration methods","[{\"question\":\"What makes electrophilic addition of alkenes so common?\",\"answer\":\"Electrophilic addition proceeds by electrophile attack on the alkene, generating a carbocation that is then attacked to form the overall product. The document states electrophilic addition is probably the most common reaction of alkenes.\"},{\"question\":\"Why does Markovnikov orientation occur in HBr addition?\",\"answer\":\"Protonation occurs at the least substituted end, producing a carbocation at the more substituted (and therefore more stable) end. The more stable intermediate leads to the observed product.\"},{\"question\":\"How do free radical conditions produce anti-Markovnikov products?\",\"answer\":\"In the presence of free radical initiators, the mechanism shifts from electrophilic addition to free radical addition using bromine radicals. The reaction forms intermediates that favor the more stable radical, reversing the regiochemistry (the peroxide effect).\"},{\"question\":\"How does hydration of alkenes give alcohols and what is its regiochemistry?\",\"answer\":\"Hydration is the reverse of dehydration and follows microscopic reversibility in the opposite order. Protonation generates a carbocation attacked by water, then deprotonation yields alcohols, with Markovnikov orientation due to the carbocation stability and where the proton and hydroxyl add.\"}]","Reactions of Alkenes - Electrophilic Addition - Orientation and Markovnikov, Radical Addition, Hydration | PDF",1791927294]