Sodium borohydride (NaBH4)...why does it do this

[Cofo]

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How (what is the mechanism) does a hydrogen from NaBH4 end up on the designated carbon in the photo I provided?

 

[Stacker]

How (what is the mechanism) does a hydrogen from NaBH4 end up on the designated carbon in the photo I provided?

Woops, I was wrong.
What actually happens is oxymercuration ensures Markovnikov's rule with hydroxyl group on the more alkylated carbon while getting rid of double bond.

The opposing Hydroboration reaction ensures anti-Markovnikov's rule with hydroxyl group on least alkylated carbon while getting rid of double bond.

 

[molar3]

you dont need to know this much detail !!!! you dont need to know mechanisms like this, maybe for your actual orgo classss but not for the DAT. just know that H and OH get added anti. i dont think u need to get any more in depth then that for DAT purposes.

 

[Cofo]

you dont need to know this much detail !!!! you dont need to know mechanisms like this, maybe for your actual orgo classss but not for the DAT. just know that H and OH get added anti. i dont think u need to get any more in depth then that for DAT purposes.

I am a person who is not satisfied with "this happens just because it does."
I actually just found a youtube video on it, and I understand the mechanism now. If I understand the details of a mechanism, then I can know WHY a reaction happens the way it does. I'm good now. It's been a while since I've taken orgo guys. Please understand this--thanks.

 

[OUDent88]

The OH is going to add to the carbon that has the methyl group on it in the anti position because of Markovnikov's Rule that it adds to the more substituted carbon and there are no carbocation intermediates so you wont have any rearrangements...but ya you really dont need the explanation for the test just remember what chad says that the important thing is the product and what that reagent does. you dont really need to know the mechanism

 

[LaughingGas]

I am a person who is not satisfied with "this happens just because it does."
I actually just found a youtube video on it, and I understand the mechanism now. If I understand the details of a mechanism, then I can know WHY a reaction happens the way it does. I'm good now. It's been a while since I've taken orgo guys. Please understand this--thanks.

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