12. Alcohols, Ethers, Epoxides and Thiols
Sulfur is right below oxygen on the periodic table. So that means it can form analogs of common oxygen-containing functional groups.
How to name sulfur-containing compounds.
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Now let's talk about the nomenclature of sulfur containing compounds. So it turns out that sulfur containing compounds are going to be named very similar to oxygen compounds because of its placement on the periodic table. If you remember, oxygen is on the second row, and sulfur is right below it on the third row. What that means is that many of the compounds that you've seen made with oxygen's, for example, alcohols and ethers can also be made with sulfur. But obviously they're gonna have different names. So what I've done here is I've made this nice chart that seems kind of confusing at first, but it really lists out every single possibility of a sulfur containing compound that you could have. Okay, it turns out that there are two main functional groups that we've learned to name for oxygen. Okay. And that would be alcohol's. Okay, where you have a terminal Ohh. Care. A terminal oxygen noticed that it's at the end of the carbon chain, and we also have Well, if you move that oxygen inside the carbon chain, it becomes an internal oxygen or what we call in either. Okay, so hopefully these two names should be familiar to you guys at this point. Because thes air oxygen containing compounds. We usually discuss these a lot before we talk about sulfur. Okay, but it turns out that sometimes these substitutes may not always get, or these oxygen's may not always get the highest priority. Okay, sometimes Oxygen's actually named as substitue INTs. And what we found is that when alcohol is named as a substitue in that means that actually has a higher priority group other than the alcohol present. Now, just so you know, side note, you haven't seen a lot of these yet in this course. Okay, but let me just give you an example of carbon cilic acid would get a higher priority than alcohol. We're going to do more of that in or go to where we name and alcohol and a car oxalic acid on the same chain for right now. I told you, as alcohol beats all because it almost always does in or go one, but later on in or go to, we will find exceptions to that. So anyway, let's say that the alcohol is a substitute, Wint. Instead of calling it alcohol, we call it hydroxy and that makes sense. So we'd say it's a one hydroxy two hydroxy, etcetera, etcetera. When Rene me as a substitute in the same way ether can also be named as a substitue int. If you recall the way that we name Ethers is to name in the AIPAC way is to name a long carbon chain and then to name the Alcock see substitue int as or the ether part as an elk oxy substitue int. Okay, so now we've just covered everything about oxygen. Now we're gonna do is we're gonna shift over here to sulfur and I'm gonna show you guys how it's really the same thing. So it turns out that sulfur can also have two possibilities. It conform on the terminal, so it means it's at the very end. It only has a one age or conform on the internal part of a chain, meaning that it has our groups on both sides. So you can see is that the sulfur at the top is a lot like an alcohol. The sulfur at the bottom is a lot like an ether. But like I said, these air not going to get the same names because then it would be very confusing. They're gonna get different names. So when a sulfur is on the terminal end and it's the route, okay, Just like alcohol is, the root is the root of the is the root of the name. Then we're gonna name it a Thile. Okay, so you can think of alcohol and file. Go together. Okay. Now, how about if the sulfur is there? But I have another high priority group present, for example, like a carb oxalic acid over here. Let's say that I had a carb oxalic acid. So what that means is that now my S h is not getting top priority. That means it's being named as a substitue int. Well, in that case, instead of calling it file, we're gonna name it Moore Capito. Now, I know that sounds really weird. That's a word that actually comes from the Latin. And if they just stuck with it, Okay, Mark Capito means sulfur in Latin. But all you need to think is that Moore Capito is similar to hydroxy. If there's a situation where I used hydroxy a substitue int, I would also use Moore Capito as the name of the substitution okay. You're only going to use my capital if there's a higher priority group present on the chain Now, finally, let's go to the ether. Analog. Okay. And for ether off a sulfur, a sulfur ether. What we're gonna name it is as a sulfide. Okay, so just think that ether is r o r Sulfide is R s are okay. I'm just gonna even write that right here. Are s are just You guys can see that it's very similar to either, but sometimes we don't name it as the common system. Remember that in the common system, we just name it as ether or sulfide. But sometimes we're gonna use the AIPAC system. And in the AIPAC system, we would name it as a substitue int. So in that case, we name it as an alcohol style, which is very similar toe Alcock see, just instead of oxy, it's file. Okay, so I know that was a lot toe walk through, but hopefully by thinking of sulfur in the context of oxygen, what you already know from oxygen, that's gonna make it easier for you. Thio, get a grasp on it. The only thing is, there's just some funky words we have to remember. Okay, so now we have some some practice problems that I want you to go ahead and do from this chart. Try to do it. Try to get the exact name. Okay for this first one, try to do the whole thing, and then I'll go ahead and give you the answer. One more thing. Just keep in mind that alcohol actually has higher priority than files. So that should be giving you an idea off. Which one to name is the substitue int and which one to name as the root. So go for it.
Note: Alcohol has higher priority than thiols.
Provide the IUPAC name for the following compound.
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Hey, guys, this video is a rerecord. Because the first time that I recorded this video, I actually got the question wrong. So that confused a lot of you. And now we're going to try it again. Okay, So what is the name of this molecule? Well, we see that we have a Thile and alcohol on the same chain. So you have to figure out which one has priority, right? And the priority actually goes toe alcohol. So what that means is that as I name this chain, I'm going to keep in mind that the one position needs to start from the side closest to the alcohol, which happens to be the carbon with the alcohol. Okay, great. So what's the longest carbon chain? Let's just go through our AIPAC rules. It would be five carbons right here. What are our substitue INTs? Well, this s H is considered a substitue int since it's on the main chain of in alcohol. So we know that's going to get the name Mark Capito, and then we have two methyl groups, so that's gonna be a dime, ethel. So let's go ahead and list out what the root name is with the modifier and then with the substitutes are so we know what the root name is going to be. One Penton. All right, that's the route. And we know that it's one pencil because I have five carbons and the O. H. Is in the one position. That means that if it keep counting, this is the three position, and then this is the four position. So what are our substitue INTs? I'm just gonna put subs. Well, I know that I have a three myr capito, and I know that I also have a four comma four die method. Now, when we name the entire molecule, we're gonna have to put it in alphabetical order. Right? So what that means is that I need to figure out is more Capito, or metal or dime Ethel before the other in the alphabet. Remember, The dies not does not count. So all I'm looking at is the ems here. So, in terms of alphabetical order, em is in the same exact place in the alphabet. So I have to go to the next letter. Let's go, T e. They're both east. Then I have to go to the next letter It's like a playoff system. The next letter is T vs Are. So this one, you might need to start saying your A b CS. But, um, if you do, you're gonna find that t is after and ours before. So that means that Moore Capito comes first. So that means that this entire name is going to be three Mark Capito, 44 die metal one pentacle. Does that make sense? Cool. So that is the answer. And again, like I know it sounds stupid with the A B C's thing. But I would rather you you say a BCS during your class or during your exam than get something like this wrong because you forgot about which one goes after tur are Okay, so we're done with this problem. Let's move on to the next one.
Provide the IUPAC name and common name for the following compound.
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so remember that it's usually easier to name ethers in the common name system, meaning that it's just both are groups and then ether at the end. Well, the same is gonna apply to sulfides sulfides air typically easier to name in the common name systems. Let's start with that one. I'm just gonna right here common. And let's figure it out. What are the two are group. So in this case, I've gotten Ethel on one side and of benzene ring by itself. It's not called benzene. It's called fennel. Okay, remember that. So I just have to put them in alphabetical order. So the common name is gonna be easy. This is just Ethel fennel sulfide. Cool. So that one wasn't so bad. You can see how if it would have been Oh, there it just would have been either same thing. Now it's cool with the AIPAC name. The AIPAC name is a little bit more complicated because remember that the AIPAC name you have to name the bulky ist or the longest route, and then you have to name the S R or the O. R. Whichever one it is as a substitue int. So in this case, I have two different possibilities. I have either the two carbon chain here. That's Ethel or I have the six carbon ring on the other side, which is fennel. Okay. As a substitue int, which one is gonna wanna be the root? I'm gonna go with my benzene ring, okay, because benzene ring is overall bigger than the two carbon chan on the other side. So what that means is that instead of calling this a fennel group, I'm just gonna call it benzene because that's gonna be the route. OK, so now if this is benzene, I'm just gonna scratch out fennel. It becomes benzene now because that's my route. Then what is the substitute? Want what My substitution is usually called. We said it's called an Al Gil file group. So in this case, the ALC you'll is just Ethel. So the name the AIPAC name here would be Ethel Sile Benzene. All one word. Okay, you might be wondering. Well, Johnny, do we have to save the location of it? Do you have to say that it's like one ethyl file Benzene? No, because there's only one substitue int. So it's always assume that you can start at the one. But you If you wanted to, you could say as well that it is one ethyl file. Benzene. Okay, but typically, if you see it, see it on your exam or in the book, you'll see that the number one is omitted. If there's only one substitute present, we usually only use locations on rings. If there's more than one substitute, for example, two or three. Okay, awesome guys, so hopeful. That made sense. Let's keep moving on.
Additional resources for Naming Thiols