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Ch. 12 - Alcohols, Ethers, Epoxides and ThiolsWorksheetSee all chapters
All Chapters
Ch. 1 - A Review of General Chemistry
Ch. 2 - Molecular Representations
Ch. 3 - Acids and Bases
Ch. 4 - Alkanes and Cycloalkanes
Ch. 5 - Chirality
Ch. 6 - Thermodynamics and Kinetics
Ch. 7 - Substitution Reactions
Ch. 8 - Elimination Reactions
Ch. 9 - Alkenes and Alkynes
Ch. 10 - Addition Reactions
Ch. 11 - Radical Reactions
Ch. 12 - Alcohols, Ethers, Epoxides and Thiols
Ch. 13 - Alcohols and Carbonyl Compounds
Ch. 14 - Synthetic Techniques
Ch. 15 - Analytical Techniques: IR, NMR, Mass Spect
Ch. 16 - Conjugated Systems
Ch. 17 - Aromaticity
Ch. 18 - Reactions of Aromatics: EAS and Beyond
Ch. 19 - Aldehydes and Ketones: Nucleophilic Addition
Ch. 20 - Carboxylic Acid Derivatives: NAS
Ch. 21 - Enolate Chemistry: Reactions at the Alpha-Carbon
Ch. 22 - Condensation Chemistry
Ch. 23 - Amines
Ch. 24 - Carbohydrates
Ch. 25 - Phenols
Ch. 26 - Amino Acids, Peptides, and Proteins
Ch. 26 - Transition Metals
Alcohol Nomenclature
Naming Ethers
Naming Epoxides
Naming Thiols
Alcohol Synthesis
Leaving Group Conversions - Using HX
Leaving Group Conversions - SOCl2 and PBr3
Leaving Group Conversions - Sulfonyl Chlorides
Leaving Group Conversions Summary
Williamson Ether Synthesis
Making Ethers - Alkoxymercuration
Making Ethers - Alcohol Condensation
Making Ethers - Acid-Catalyzed Alkoxylation
Making Ethers - Cumulative Practice
Ether Cleavage
Alcohol Protecting Groups
t-Butyl Ether Protecting Groups
Silyl Ether Protecting Groups
Sharpless Epoxidation
Thiol Reactions
Sulfide Oxidation
Additional Guides
Hydroxyl Group

There are 3 distinct ways to name cyclic ethers. But before we get into them, let’s first specifically define what an epoxide is.  

Concept #1: Defining what an epoxide (oxirane) is.


All right guys, so now let's talk about naming epoxides. It turns out that epoxides are just cyclic ethers. That's basically the definition. Some types of cyclic ethers, remember that an ether is ROR, are going to be named as their own functional group due to increased reactivity.
The specific ones that we usually name as their own functional group are three-membered ethers because there happens to be a lot of strain in those rings. They're out of their normal bonding preferences or their normal angle preferences. What that means is that they're very reactive and it's very easy to open them up.
What we call these three-membered cyclic ethers is – there's actually two common names for them. We call them epoxides, so go ahead and write that down. They're also called, in some textbooks, some professors like to use the word oxirane. These are really synonyms for each other. An epoxide and an oxirane are the same exact thing. It's just a three-membered cyclic ether. 

Cycloalkane Convention

Name the ring as a cycloalkane, adding the prefix oxa- and location if necessary.

Concept #2: How to name cyclic ethers using the cycloalkane convention.  


Cool so far, right? Now the challenge becomes how do we name these guys because sometimes, first of all, they're not always three-membered rings and second of all, there's a lot of substituents. So it turns out that there's three different common ways to name epoxides and I'm going to go over all of them right now.
Let's start off with what we call the cycloalkane convention. In this type of naming system, what we do is we name the entire ring as if it was an alkane first. As you can see here I have a six-membered ring, but how many of those atoms are actually carbons? Only five of them are. I've got 1, 2, 3, 4, 5. Now you might be wondering why I started the one there. I didn't need to. I'm just using that – maybe I did, but I'm just using that as an example right now just to count carbons.
I have five carbons, but what I'm telling you is that we should actually name it as a cycloalkane, not by the number of carbons. What that means is that usually when we're naming an alkane we would say there's five carbons, so this would be cyclopentane, but it's not. We're going to call this actually cyclohexane because we go by the shape. What we're worried about here is the shape of the molecule, not how many carbons it has in it. So this would be a cyclohexane first of all as our root.
Now the difference is if we have oxygens inside of a ring, which is by definition a cyclic ether. Then we're going to add the prefix oxa-. What oxa- is going to tell us is there's one member of this ring that is an oxygen. So if I call it oxacyclohexane, what I'm saying is that I have a six-membered ring where one of the atoms is an oxygen, not a carbon. Then, obviously, location if necessary.
Let's go ahead and just talk about this for a second. The root is going to be the oxacyclohexane. I have that written here. Now we just have to talk about location. How do we know where to put those guys? Well, it turns out that the oxygen is always going to get your one spot. When I put the one here, that didn't really count. That wasn't true numbering. The way that I should really number it is starting from the oxygen because that's the highest priority atom inside the ring. Then, obviously, I should number to give the lowest overall number or to go to the next highest priority, etcetera. This would be 3-methyl-1-oxacyclohexane. Cool so far?
Just so you guys know, this also applies to rings that have more than one oxygen. If I had two oxygens, that would be what was called a dioxide. Just putting that out there. You could use prefixes as well.
Now let's go ahead and talk about another naming system, by the way, one word really quick. This is going to be commonly used for non-three-membered rings. If not three-membered, as you can see I was dealing with a six-membered one here, this is usually the one we use. If it's four-membered, five-membered, six-membered, etcetera, you would use this naming system. Now if it is a three-membered ring, we could still use it, but this is not going to be the most common way to name it. 

Epoxy Convention

Name as a typical alkane, and then include epoxy as a di-located substituent. 

Concept #3: How to name epoxides using the epoxy convention.


If we are dealing with a three-membered ring, there's much more common ways. One is the epoxy convention. What the epoxy convention basically says is this: we have a substituent named an epoxy group. We're just going to name our longest carbon chain as normal and then label the three-membered ring as just a substituent coming off of that chain and obviously give it the lowest number.
One other thing about this that's interesting is that you actually have to name the locations of both of the atoms that the three-membered ring is attached to. As you can see here my epoxide is going to get priority over the methyl, so I would choose this to be my first carbon over here. That means that my epoxy group is – or my epoxy substituent is across the 2 and the 3. Therefore, I'm actually going to call this a 2,3-epoxy substituent because I'm basically saying that I have a bond to O across those two carbons.
Then the rest of it, we're just going to name like always. So this would be 2,3-epoxy-5-methylhexane. Not so bad, right? That's just something to consider that you could also use the epoxy convention. It's perfectly legit. 

Oxide Convention

Name as an imaginary alkene, then follow with the word oxide

Concept #4: How to name epoxides using the oxide convention.


Now there's on top of that there's even one more way to name Epoxides and that this one actually comes from even further back in the history this one is actually like a reaction, OK? What they're basically saying is name it as and Alkene so pretend that an epoxy wasn't even there replace it with an alkene, OK? Name it as the alkene the entire name and then at the end just add the word oxide, OK? Now how does that make sense? The reason that makes sense is because what we're saying is that we're basically assuming that we start off with a double bond and then we did in the epoxidation to put in an epoxide group on that double bond, now you might not know how to do that yet and that's fine we're going to actually learn that pretty soon but I'm just saying that this is almost coming from the reactivity side of things saying well I could start from a double bond and if I do an Epoxidation I could get in an Epoxide so then I would call it an oxide of that double bond, OK? So in this case I would call this.... This would be hexane, right? Because I got a six membered chain, notice that my double bond would be across the two and the three but the way that I name double bonds is different from the way that I name epoxides, I actually don't say this is a 2-3 alkene I would just start where at the lowest number so in this case this is actually going to be what we call the 2 hexanes so don't get the them confused this would never be called a 2-3 hexane you only do that for an epoxy substituent, OK? So we know you have a 2 hexane now we need a substituent, the 5-methyl, right? On the five so this would be a 5 methyl 2 hexeneoxide, alright? So just so you know if your professor requires stereochemistry if your professor is asking about stereo chemistry remember that's just like cis and trans stuff then you would have to provide it here, OK?

Note: I forgot to address in the videos that both of these would be trans due to the alkyl groups facing opposite sides of the ring.

Practice: Which of the following is the correct name of the following compound:

Practice: Which of the following is the correct name of the following compound: