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Organic Chemistry

Learn the toughest concepts covered in Organic Chemistry with step-by-step video tutorials and practice problems by world-class tutors.

12. Alcohols, Ethers, Epoxides and Thiols

Sulfide Oxidation

Sulfides are more reactive than their oxygen-containing analogs, ethers, because they have an expanded octet and can form additional bonds with other atoms. They are particularly susceptible to oxidation.

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Quick overview of oxidation.

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Now we're going to explore the oxidation reactions of sulfides. So before we can talk specifically about sulfides, I think we need a little refresher on what oxidation is. Okay, Because it might have been a little while since you saw oxidation reduction. Just remember that oxidation is any reaction that's gonna involve the increase in the oxygen content off a molecule. Now, that doesn't mean that you're actually adding oxygen's. It could just mean that you have more bonds two and oxygen. Okay, so this is a scheme, a little table that I used during my oxidation reduction lectures. And what you should know about it is just you can see the pattern as you move to the right. These molecules have more and more bonds toe oxygen. So if you think about it a sulfide, what does a sulfide look like? We're gonna look at it in a second, but it's a sulfur with zero oxygen's on it. Okay. So as we oxidized, we would we would expect that we're gonna get more and more bonds to oxygen. Cool

Oxidation reactions involve an increase in the oxygen content of a molecule.

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Reagents used to oxidize Sulfides.

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So one thing to keep in mind is that sulfides typically sulfides are the analog oven ether. Okay, if you look at this sulfide down here, it's basically an ether. Right. Except instead of having an oxygen has a sulfur. Okay, ethers we've learned in the past if you guys have watched my ethers lectures, then we're going to see is that ethers don't really react anything. They're very, very difficult to make react. But sulfides are actually gonna be more reactive because they haven't expanded expanded octet. Remember that the expanded octet means that they can fit up to six bonds with the sulfur, so it's gonna give it more liberty to react with oxygen. Okay? And that means that they're really gonna be pretty easy to oxidize. So before we talk with the re agents, I just want to talk about how to recognize these functional groups because they know that their new you know, we don't see them alive. Remember that a sulfide is an ether with a sulfur. Okay, now a so fox side would be once I've oxidized it. One step. I'm gonna get to Seoul Fox side now. So Fox Side is really the sulfur analog of a key tone. Okay, so it's and I've got my key tone usually has a carbon in the middle, but I'm changing it for a sulfur. That would be a soul Fox side. Okay, so that's one way to remember it. But it turns out that the soul Fox, I really could be oxidized again because sulfur can have up to six bonds. So if I want to oxidize it even more, I could take it all the way upto a soul phone. Now, cell phone. There really isn't anything that I can use to help you think of it because we've never really named. We haven't really been naming a lot of molecules that had six bonds. So it's not like I can compare it to anything from a carbon structure, but just committed to memory. A cell phone is the most oxidized form of a soul of ah sulfide. Okay, so now how do we go from one to the other? Well, it turns out that most oxidizing agents are actually gonna go all the way to the soul phone. Okay? Because, like I said, our sulfides easy to oxidize. Yes. Okay, so almost all oxidizing agents will take it all the way to the cell phone. Usually we're talking about hydrogen peroxide. It's a pretty strong oxidizing agent. Also, Canada four, right? Came into force like that famous oxidizing agent. We used for a ton of things. And both of them are gonna be able to take a sulfide directly to the cell phone without stopping in the middle. But what if I really want to stop? I really want to just oxidize it to a self oxide and not get the cell phone. Okay. Well, then we're gonna use a very particular re agent. Okay, So if I use an N a Iot four Okay with that's going to give me is that's gonna give me a partial oxidation. Okay. By the way, that's called sodium period. Okay, sodium period. Let me just write it down. CS can know, in case you see it, sodium period dates. Okay, So if you react sulfide with sodium period eight, what that's going to give you is instead of a full oxidation, it's only gonna give a partial oxidation to the self oxide, and it's gonna stop. So if you act the soul fox side with sodium period. Eight. There's no reaction because it can't oxidize the soul. Fox side. But if you do have the self oxide and you say, Hey, I'm bored of this, I want to just take it all the way to the cell phone. You can always use hygiene products that again, okay. Or even Canada. Four. Okay, just letting you know that if you ever want to stop in this middle stage, you would use sodium period. Okay, so, really, this is not there is not a very hard topic. I just wanna introduce these three different oxidation states of sulfur and let you know what the different reagents, our hope that made sense. Let me know if you have any questions.
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