If oxymercuration reactions are anti additions, how come one of these examples looks like anti, and the other one looks like syn? Would someone be able to draw out both mechanisms? Oxymercuration-Demercuration ReactionOAcmercurinium ion*Hg(OAc)HgOxymercuration-Demercurationc=c + Hg(OAc);NaBH4 ,HỎ HgOAcНОH(Markovnikov orientation)Hg(OAc)Hg(OAc)ig(OAc)Markovnikov addition of water to the double bondH3O*Hö:H-0::OHMilder conditions than direct hydrationH,ö Horganomercurial alcohol• No rearrangements or polymerization© 2017 Pearson Education, Inc.

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Oxymercuration- Demercuration Reaction OAc mercurinium ion Hg(OAc) Hg* Oxymercuration-Demercuration c-c • Hg(OAc) H,0 HỎ HgOAc но H (Markovnikov orientation) *Hg(OAc) Hg(OAc) Hg(OAc) • Markovnikov addition of water to the double bond C-C- -C-C- H;O* H,ö: :OH • Milder conditions than direct hydration Hö: organomercurial alcohol • No rearrangements or polymerization O 2017 Pearson Education, Inc.

Oxymercuration- Demercuration Reaction OAc mercurinium ion Hg(OAc) Hg* Oxymercuration-Demercuration c-c • Hg(OAc) H,0 HỎ HgOAc но H (Markovnikov orientation) Hg(OAc) Hg(OAc) Hg(OAc) • Markovnikov addition of water to the double bond C-C- -C-C- H;O H,ö: :OH • Milder conditions than direct hydration Hö: organomercurial alcohol • No rearrangements or polymerization O 2017 Pearson Education, Inc.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter7: Alkenes: Structure And Reactivity

Section7.SE: Something Extra

Problem 24VC: The following carbocation is an intermediate in the electrophilic addition reaction of HCl with two...

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