[{"data":1,"prerenderedAt":-1},["ShallowReactive",2],{"detail-sidebar-cat-1-en-105":3,"doc-seo-572416-105":53,"doc-detail-572416-en":120},{"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":113,"head_meta":115,"extra_data":117,"updated_unix":119},105,"en","chem-350-jasperse-ch-8-handouts","Chem 350 Jasperse Ch. 8 Handouts","","Chem 350 Jasperse Chapter 8 handouts summarize key alkene reactions, focusing on reaction orientation, stereochemistry, and mechanistic reasoning. The material emphasizes memorizing which outcome occurs under specific conditions, including HBr addition with and without peroxides, Markovnikov versus anti-Markovnikov regiochemistry, and cis/trans stereochemical results. Additional sections cover Br2 (or Cl2) outcomes, acid-catalyzed processes, epoxide hydrolysis, and related elimination reactions, with stepwise guidance for drawing mechanisms and propagation steps.",{"@graph":63,"@context":112},[64,80,95],{"@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":46,"@type":70,"position":76},"https://docshare.wps.com/template/paper-templates/",3,{"item":78,"name":59,"@type":70,"position":79},"https://docshare.wps.com/template/chem-350-jasperse-ch-8-handouts/572416/",4,{"url":78,"name":59,"@type":81,"author":82,"headline":59,"publisher":85,"fileFormat":88,"inLanguage":57,"description":61,"dateModified":89,"datePublished":89,"encodingFormat":88,"isAccessibleForFree":90,"interactionStatistic":91},"DigitalDocument",{"name":83,"@type":84},"CatatanPagi","Person",{"url":68,"name":86,"@type":87},"DocShare","Organization","application/pdf","2026-10-13",true,{"@type":92,"interactionType":93,"userInteractionCount":4},"InteractionCounter",{"@type":94},"ViewAction",{"@type":96,"mainEntity":97},"FAQPage",[98,104,108],{"name":99,"@type":100,"acceptedAnswer":101},"What does the handout require students to memorize for alkene reactions in Chapter 8?","Question",{"text":102,"@type":103},"Memorize reaction, orientation where appropriate, stereochemistry where appropriate, and mechanism where appropriate. It also highlights that outcomes depend on the specific reaction conditions shown in the handouts.","Answer",{"name":105,"@type":100,"acceptedAnswer":106},"How does HBr addition differ with or without peroxides?",{"text":107,"@type":103},"With peroxides, bromination leads to both cis and trans outcomes, while without peroxides the results follow the stated regiochemical and stereochemical rules in the summary table. The handout links these outcomes to the correct mechanistic reasoning.",{"name":109,"@type":100,"acceptedAnswer":110},"Why do elimination reactions use different base choices (normal vs bulky)?",{"text":111,"@type":103},"Normal bases favor Zaytsev elimination, while bulky bases (NEt3 or KOC(CH3)3) promote Hoffman elimination. The handout also notes how these choices affect whether E2 dominates and when SN2 competes, especially for 2º versus 3º substrates.","https://schema.org",{"og:url":78,"og:type":114,"og:title":59,"og:site_name":86,"og:description":61},"article",{"robots":116,"canonical":78},"index,follow",{"doc_id":118,"site_id":56},572416,1791927294,{"code":4,"msg":5,"data":121},{"doc_id":118,"user_id":122,"nickname":83,"user_avatar":123,"doc_module":9,"category_id":45,"category_name":46,"doc_title":59,"doc_description":61,"doc_content":124,"file_id":125,"file_url":126,"file_type":127,"file_size":128,"view_count":4,"is_deleted":4,"is_public":9,"is_downloadable":9,"audit_status":9,"page_count":129,"language":130,"language_code":57,"site_id":56,"html_lang":57,"table_of_contents":131,"faqs":132,"seo_title":133,"seo_description":61,"update_tm":119,"read_time":15},962090894170,"https://ap-avatar.wpscdn.com/davatar_6f874abed73319feea01a86fa6f0fab8","Chem 350 Jasperse Ch. 8 Handouts 1  \nSummary of Alkene Reactions, Ch. 8.   \nMemorize Reaction, Orientation where Appropriate, Stereochemistry where Appropriate, and Mechanism where Appropriate.  \n-all are drawn using 1-methylcyclohexene as a prototype alkene, because both orientation and stereochemistry effects are readily apparent.  \n1  \n2  \n3  \n4  \n5  \n6  \n7  \nOrientation  Stereo  Mechanism  \nHBr  \n(no peroxides)  \n Br  \nCH3  \n HBr H  \nperoxides  Br both cis and trans  \nMarkovnikov  \nAnti-Markovnikov  \nNone  \nNonselective. Both cis and trans  \nBe able to  draw  completely  \nBe able to  draw  propagation  steps.  \nMarkovnikov  \nMarkovnikov  \nAnti-Markovnikov  \nMarkovnikov  \nNone  \nNone  \nCis  \nNone  \nBe able to  draw  completely  \nNot  \nresponsible  \nNot  \nresponsible  \nNot  \nresponsible  \nNone  Cis Not  \nresponsible  \nChem 350 Jasperse Ch. 8 Handouts 2  \n8  \n9  \n10  \n11  \n12  \n13  \n14  \nBr2  \n(or Cl2)  \nCH3  \nBr  \nHBr  \nCH3  \nOH  \nOH H  \nNote: H-bearing alkene carbon ends up as aldehyde.  \nH-bearing alkene carbon ends as carboxylic acid  \nOrientation  \nNone  \nMarkovnikov  \nNone  \nNone  \nNone  \nNone  \nNone  \nStereo  \nTrans  \nTrans  \nCis  \nTrans  \nCis  \nNone  \nNone  \nMechanism  \nBe able to  draw  completely  \nBe able to  draw  completely  \nNot  \nresponsible  \nBe able to  draw acidcatalyzed  epoxide  hydrolysis  \nNot  \nresponsible  \nNot  \nresponsible  \nNot  \nresponsible  \nChem 350 Jasperse Ch. 8 Handouts 3  \nSummary of Mechanisms, Ch. 7 + 8.   \nAlkene Synthesis and Reactions.  \n1  \n2  \n3  \nHBr  \n(no peroxides)  \n Br  \nCH3  \n HBr H  \nperoxides  Br both cis and trans  \nH Brominate  \nHBr  \nHydrogen Transfer  \n| Note 1 : For unsymmetrical alkenes , bromination occurs at the less substituted alkene carbon so that the more stable radical forms\u003Cbr>(3º > 2º > 1º) , in keeping with the product stability-reactivity principle | | vs. | |\n| --- | --- | --- | --- |\n\nNote 2: Hydrogenation of the radical comes from either  \nface, thus cis/trans mixture results  \ntop  \nbottom Br  \nH  \ncis  \ntrans  \nCH3  \nH  \nBr H  \nH CH3  \nBr H  \nNote: For unsymmetrical alkenes, protonation again occurs at the less substituted end of the alkene, in order to produce the more stable radical intermediate (3º > 2º > 1º)  \nChem 350 Jasperse Ch. 8 Handouts 4  \nH  \nO   \nH -H  \nHHgOAc  \nDeprotonate  \nOH  \nHHgOAc  \n NaBH4 OH HH  \n5  \n 1. BH3•THF CHH3  \n2. H2O2, NaOH  \nOH  \nCH3  \nH  \nBH2  \nCH3  \nH  \nOH  \nNotes  \na. concerted addition of B-H across C=C  \n-explains the cis stereochemistry  \nb. the B-H addition is Markovnikov; the B is !+ , the H is !-  \nc. The H2O2, NaOH process is complex, but replaces the B with OH with complete retention of stereochem  \n-the explains why the cis stereochemistry established in step one is preserved in step  \nChem 350 Jasperse Ch. 8 Handouts 5  \nCH3  \nBr  \nHBr  \nH  \nCation  \nCapture  \nBr  \nBr  \n3 Notes  \n1. Cation intermediate is cyclic bromonium (or chloronium) ion  \n2. The nucleophile captures the bromonium ion via backside attack  \n-this leads to the trans stereochemistry  \n3. The nucleophile attacks the bromonium ion at the *more* substituted carbon  \n9  \nBr2, H2O  \n(or Cl2)  \nCH3  \nOH  \nHBr  \nBr  \nO  \nOH2  \nH  \nCation  Br  \nCapture  \nH  \nH  \nH  \nBr Br  \nH  \nH  \nBr  \nOH  \n-H  \n4 Notes  \n1. Cation intermediate is cyclic bromonium (or chloronium) ion  \n2. The nucleophile captures the bromonium ion via backside attack (ala SN2)  \n-this leads to the trans stereochemistry  \n3. The nucleophile attacks the bromonium ion at the *more* substituted carbon-this explains the orientation (Markovnikov)  \na. There is more + charge at the more substituted carbon  \nb. The Br-C bond to the more substituted carbon is a lot weaker  \n4. Alcohols can function in the same way that water does, resulting in an ether OR rather than alcohol OH.  \nChem 350 Jasperse Ch. 8 Handouts 6  \n10   PhCO3 H  CH3  \n   O  \nH  \n ONE CH3 \" \\#+  H  \n~~ ~~ ! \"  STEP! ! + !! OO  O  \n! ! No   \\#$   \n ions \" Ph Ph  \nPh Carbonyl-hydrogen  \nHydrogen-bonded reactant  \nNotes  \n1. Comp","cbCair3PH3DxVvBg","https://ap.wps.com/l/cbCair3PH3DxVvBg","pdf",2123644,33,"English","# Orientation, Stereochemistry, and Mechanism (Ch. 8)\n## HBr Addition (with/without peroxides)\n## Br2 (or Cl2) Addition and Notes\n## Summary of Mechanisms (Ch. 7 + 8)\n## Radical/Markovnikov vs anti-Markovnikov Logic\n## BH3•THF and NaBH4 / Oxyfunctionalization Notes\n## Bromonium/Chloronium Ion Cation Capture\n## Epoxide and Water/Peracid Pathways\n## Os-mediated Cis Addition and Hydrolysis\n# Chapter 7 Review and Elimination Concepts\n## E2 with Normal vs Bulky Bases\n## Acid-Catalyzed E1 Elimination\n# Ch. 8 Introduction: Reactions of Alkenes","[{\"question\":\"What does the handout require students to memorize for alkene reactions in Chapter 8?\",\"answer\":\"Memorize reaction, orientation where appropriate, stereochemistry where appropriate, and mechanism where appropriate. It also highlights that outcomes depend on the specific reaction conditions shown in the handouts.\"},{\"question\":\"How does HBr addition differ with or without peroxides?\",\"answer\":\"With peroxides, bromination leads to both cis and trans outcomes, while without peroxides the results follow the stated regiochemical and stereochemical rules in the summary table. The handout links these outcomes to the correct mechanistic reasoning.\"},{\"question\":\"Why do elimination reactions use different base choices (normal vs bulky)?\",\"answer\":\"Normal bases favor Zaytsev elimination, while bulky bases (NEt3 or KOC(CH3)3) promote Hoffman elimination. The handout also notes how these choices affect whether E2 dominates and when SN2 competes, especially for 2º versus 3º substrates.\"}]","Chem 350 Jasperse Ch. 8 Handouts | PDF"]