How Does This Reagent- Hg(OAc)2/H2O Then NaBH4- React With An ...

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You are using an out of date browser. It may not display this or other websites correctly.You should upgrade or use an alternative browser. How does this reagent- Hg(OAc)2/H2O then NaBH4- react with an alkene?

• Thread starter Thread starter Lazerous
• Start date Start date Aug 5, 2008

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Lazerous

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Members do not see this ad. And whatever the product is, will it be markovnikov or anti-markovnikov? Sort by date Sort by votes A

artanis

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Hey there, This reaction is markovnikov. But more importantly, the reason it is markovnikov is due to the fact that there is a mercurinium intermediate in the mechanism and the water molecular attaches to the carbon that is more highly substituted, letting go the mercury-acetate. The NaBH4 is there to cleave the mercury acetate on the less substituted carbon for a hydrogen. I hope this makes sense. Upvote 0 Downvote

PooyaH

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It adds cis-OH and H to the alkene and it's markovnikov. Upvote 0 Downvote L

Lazerous

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artanis said: Hey there, This reaction is markovnikov. But more importantly, the reason it is markovnikov is due to the fact that there is a mercurinium intermediate in the mechanism and the water molecular attaches to the carbon that is more highly substituted, letting go the mercury-acetate. The NaBH4 is there to cleave the mercury acetate on the less substituted carbon for a hydrogen. I hope this makes sense. Click to expand...

Yes it does. Thanks! Upvote 0 Downvote A

artanis

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PooyaH said: It adds cis-OH and H to the alkene and it's markovnikov. Click to expand...

it does not add cis. Anything that has a bromonium, chrolonium, in this case Mercurinium intermediate, it will be ANTI (not cis). The one that is "SYN" addition is the hydroboration which is known as the ANTI-markovnikov reaction. This is gonna be on there for sure so know it, either the anti-markovnikov addition to an alkene, or to an alkyne, but for the alkyne know that tautomorization occurs to produce an aldehyde. Upvote 0 Downvote

PooyaH

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artanis said: it does not add cis. Anything that has a bromonium, chrolonium, in this case Mercurinium intermediate, it will be ANTI (not cis). The one that is "SYN" addition is the hydroboration which is known as the ANTI-markovnikov reaction. This is gonna be on there for sure so know it, either the anti-markovnikov addition to an alkene, or to an alkyne, but for the alkyne know that tautomorization occurs to produce an aldehyde. Click to expand...

You're right. I meant to say the overall product would be anti addition. Last edited: Aug 5, 2008 Upvote 0 Downvote J

Jessi4eve

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Markovnikov anti addition of water to double bond WITHOUT rearrangements. That's the correct answer in 10 words.😀 Upvote 0 Downvote C

Contach

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Jessi4eve said: Markovnikov anti addition of water to double bond WITHOUT rearrangements. That's the correct answer in 10 words.😀 Click to expand...

what type of rearrangement are u talking about? and how does an alkyne addition tautomerize into an aldehyde??? Upvote 0 Downvote D

dentalknight

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Contach said: what type of rearrangement are u talking about? and how does an alkyne addition tautomerize into an aldehyde??? Click to expand...

no rearrangements means no hydride or methyl shifts. and an alkyne tautomerizes into an aldehyde when the triple bond is between the second to last and the last hydrocarbon. The triple bond will reduce to a double bond with an OH group connected to the last carbon. This enol will tautomerize into an aldhyde with resonance causing a more stable carbonyl resulting in an aldehyde. hope that makes sense Upvote 0 Downvote A

artanis

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dentalknight said: no rearrangements means no hydride or methyl shifts. and an alkyne tautomerizes into an aldehyde when the triple bond is between the second to last and the last hydrocarbon. The triple bond will reduce to a double bond with an OH group connected to the last carbon. This enol will tautomerize into an aldhyde with resonance causing a more stable carbonyl resulting in an aldehyde. hope that makes sense Click to expand...

This is correct. To add to this, if you add an -OH group to the markovnikov position of a terminal alkyne (i.e. carbon 2), it will tautomerize into a KETONE not an aldehyde. So the carbon 2 participates in the carbonyl group. So if you want an aldehyde from a terminal alkyne, add hydroborate it with either 1. 9-BBN, THF 2. H2O2, NaOH Last edited: Aug 5, 2008 Upvote 0 Downvote A

artanis

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Contach said: what type of rearrangement are u talking about? and how does an alkyne addition tautomerize into an aldehyde??? Click to expand...

Okay, for adding an -OH, the only time you can get hydride/alkyl shifts is when you straight up add water in presence of acid. The mechanism has a carbocation intermediate and therefore it will do necessary hyrdride/methyl shifts in order to form the more stable carbocation. The reason why oxymercuration for a means of adding an -OH in the markovnikov sense is that there is no shifts possible due to the mercurinium ion formed in the intermediate. Upvote 0 Downvote

Mamona

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.. Upvote 0 Downvote N

nixon13

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i always couple hydroboration and oxymercuration together. They are like reciprocals. Hydroboration adds anti-mark and the OH and H are cis. Oxymercuration adds markovnikov and OH and H are anti. Upvote 0 Downvote You must log in or register to reply here. Share: Facebook X Bluesky LinkedIn Reddit Pinterest Tumblr WhatsApp E-mail Share Link

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