12. Alcohols, Ethers, Epoxides and Thiols
Making Ethers - Alkoxymercuration
Same reagents as oxymercuration, except with alcohol as the nucleophile instead of water.
The Mechanism of Alkoxymercuation.
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another way that we can synthesize ether is through a reaction called Alcock Seamer Curation. And you might immediately notice that this sounds a lot like another reaction that you're supposed to know by now. And that's Oxy Mercury ation. So it turns out that there's going to be the same exact mechanism as Oxy, Mercury ation or Oxy Merck. Except that in the top re agent in the In the Oxy Mercury ation step, we're gonna use alcohol as our nuclear file instead of water. Okay, so what you can see is that the biggest difference here is this right here I have alcohol in place of the water, and that's gonna make an ether instead of an alcohol. Okay, so let me just walk you guys through this mechanism really quick. So remember that what we get is h g. Always see Oh, a c Oops. That came out weird. There we go. Oh, a c. And in the first step, what we do is the dull bon attacks. The mercury kicks out, one of the always sees and the mercury attacks back. So we wind up making is, uh, bridge an ion bridge. So what? That's gonna look like is like this Where now I have a dotted partial bond to H G. It's only a touch toe one always see now dotted, partial and a positive charge. Okay. And there should be. Actually, there should be a dotted partial bond here, too. And a positive charge. Okay, so now we've got our intermediate notice that we can't get any shifts because there's no carbon cat ion. And now this is the part that, typically, water would come in and attack. Which side do you remember in this case? I have a Markov Nick off site here, and I have an anti Murkoff Nick off site there. Which one would it attack Markov Nick off? Because that's gonna be the one with the most positive character. But instead of water, what's actually gonna attack is in this case, ethanol. Okay, so my water attacks. I'm sorry. My ethanol attacks kicks out the h G and what I wind up getting is something. Looks like this. I'm gonna try to fit in here. Where? Now let's say that the alcohol attacks from the bottom. Then I would draw that the H g, the mercury attacks from the top We're not attacks, but is now placed in the top. Okay, cool. Awesome. So that's the end of the oxy Merck step. Okay, in this case, Alcock see Merck because I used ethanol. Okay, then remember that we have a reduction step. The reduction step is just any bh four and O h negative. And you don't need to know the mechanism for this. So I'm just gonna say, don't need to know mechanism. Okay, But what we do need to know that happens is that we'll remember there was a positive charge on that. Oh, actually, Okay. And what's gonna happen is that I'm gonna wind up reducing the mercury just to an h. So this is gonna become h okay. And I'm gonna wind up deep protein ating my oxygen. So now look what that turns into It turns into either okay, because now what I have is our Oh, are the weird looking either, but it is an ether, so I get either as my product and that's it. It's the same as Oxy Merck, Except that you have to just now you have to be aware every time you see an oxy Merck, make sure that you look to see whether it's water or alcohol, that's attacking because that will make a world of difference in terms of what your product looks like. All right, so I hope that made sense. Same exact things before. We're just using alcohol instead. All right, so let's go ahead and move on.
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