Organic Chemistry

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

19. Aldehydes and Ketones:Nucleophilic Addition

Oxidation of Alcohols

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concept

Reagents

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alright guys not want to dive a little deeper into the re agents of oxidation. So just you know, all of these regions that we're gonna talk about in this topic can be generalized as oxidizing agents. Okay, Now, I remember when I was in Jenkin and you had, like, oxidizing agents, reducing agents. Oxidation is kind of confusing. Sometimes, like the oxidizing agent gets reduced, there's a lot of different stuff up to memorize. Um, or maybe I was just stupid. I don't know, but all I know is that in or go, it's really not complicated at all. All you have to think about is that the oxidizing agent is the thing that oxidizes your molecule. Okay, so if you're trying to oxidize molecule, make more bonds to oxygen, you're going to use an oxidizing agent. It's that easy. Okay, so, um, what's There's a general rule they really need to follow with all these reactions. Even if you don't know the mechanism, there's just a rule that you can use. And that's that oxidizing agents are gonna add as much oxygen as possible while not breaking any carbon carbon bonds. Okay, now, this is a little bit of a lie. There are some oxidizing regents oxidizing regents that can break carbon carbon bonds. Okay, some examples that you might already know would be, for example, owes analysis. Okay, That would be an example of an oxidation that can. But that's what we're going to talk about in this topic. That's its own separate topic. Right now. I'm trying to deal with these oxidizing agents that don't break carbon carbon bonds. Okay, so I'll get to what they are in a second. But even before we know what the re agents are, we could already jump into a practice problem. What I'm wondering is out of these four molecules here, which of them actually could be oxidized? What I'm basically saying is, how many of them could you add? Bonds toe oxygen without breaking a carbon carbon bond? All right, so I'm gonna go ahead and let you guys figure that out. Get back to me. Which of these could be oxidized?
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example

Strong oxidizing agents

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All right. So I hope that you didn't say all of them. Because there are some that can, and some that can't let me give you an example. The first one there's a carbon here that has a bond to an oxygen has to bonds to carbon. And then it has one bond to H. Would you agree with that? Okay, so now my question is, is there a way that I could turn this carbon into a carbon that has more bonds toe oxygen? Okay. And here's the way up to think about you have to think Well, how many bonds to carbon does it already have? Has to has won two bonds to carbon. Is that cool so far since as to bonds to carbon. How maney total bonds Could it have toe oxygen? Theoretically to because no matter what, carbon could on Leah. Four bonds. So what that means is that if has to bonds to carbon later on, I could oxidized. It's that it has to bonds toe oxygen. Alright. So could this be oxidized? Yes, this could be oxidized because I could make it in the form where there's two bonds to oxygen. All right, So let's move on to the next one. The next one. This carbon. Could it be oxidized? No. This one is not gonna be able to be oxidized because noticed that it already has its maximum number of bonds. Oxygen, Because has two carbons 12 Is there a way to add a third bond to oxygen? No. Okay, let's move on to three. Could three be oxidized? Yes. OK, because it only has one bond to carbon. So that means if it only has one bond to carbon, then it could have how many bonds to oxygen? Three. How many bonds does I have right now? Onley One. So it could actually be oxidized more than once. OK, and then finally we have compound number 43 gets a check. Mark four. Could this carbon be oxidized? Yes, once again, because it only has one bonds of carbon. So that means that we could take away that h. And we could make another bond to oxygen there. All right, so that's the way that it works. All of these could be oxidized, except for two, which can't, because it already has the maximum number of bonds to carbon and oxygen. All right, So what reagents are gonna do this? Well, strong oxidizing agents are agents that are going to add the maximum number of oxygen's possible while following the rule of not breaking any carbons. Okay, these re agents are gonna be cam in all four. Okay, Canada four is a region that you've probably already seen. But in case you haven't potassium permanganate. Very strong oxidizing agent. Also your chromium six re agents. Okay, now it's a CR six. Plus, remember, that is the oxidation state of the atom. You are not going to calculate oxidation states in organic chemistry. But you should know is that if you see chromium present in any of these weird molecules, these are all examples of strong oxidizing agents. Okay, It turns out there's more re agents than this. The Jones re agent is an example of of a chromium re agent. Okay. Where Jones region would use c r. 03 and sulfuric acid. Okay, so I'm trying to say is that as long as you see some kind of chromium in the regent think this is a strong oxidizing agent, you don't have to actually calculate out the oxidation state Okay, So what I want us to do for this next practice problem is go ahead and draw the new oxidation products of each of these molecules. Okay, So I want four different things in these boxes. If it's not going to react, put no reaction, Okay? But I want to see all the different oxidation products, so go ahead and try to do the first one.
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example

Strong oxidizing agents

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So let's go ahead and look at this first one. What I would get is a carbon that now has two bonds to carbon. So I should draw that six numbered ring just like before. But now it's gonna have to bonds toe oxygen. So what I'm expecting to get here is a key tone. Okay? Why a key tone? Because a key tone would be the version of that carbon has to bonds toe oxygen. Now you might be like Johnny. How would I know if it's a key tone? How? But if it's another functional group, I don't want you to think about the functional group. Honestly, all I want you to think is how maney bonds to oxygen does. This thing is this thing able to make in this case that carbon could make to bonds to oxygen because that's why you draw to bonds to oxygen and a cyclo hexane on the other side. All right, so go ahead now and try to do the other three another. You have an example. Try to draw the other three structures, put them in the box and see if you get the right products
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example

Strong oxidizing agents

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All right, so this first one would be no reaction. We know that because we said that the second molecule can't be oxidized at all. So there's no point and even drawing a product now, the third one is interesting because we talked. We talked about how this carbon right here has only one bond toe, another carbon. So that means it has one bond to carbon. How maney Oxygen's Can it possibly have three. So what that means is that I need to draw a version of this carbon that's gonna three bonds to oxygen. If you looked at our intro to Redox chart, where I talk about things that are getting oxidized and things they're getting reduced. Okay, The version of carbon with three oxygen's would be a carb oxalic acid. So what I would do is I would draw that carbon with a dull bond. Oh, and with an O. H. Okay. What that's going to do is now that's gonna keep my carbon carbon bonds. So I'm not breaking the rule. I'm not breaking that bond, but now I have one, 23 bonds, toe oxygen. All right, cool. So no. How about this last one Well, this last one, I'll move out of the way. Stairs can see it. This last one you will find is that that carbon once again on Lee had to bonds to I mean, I only had one bond to carbon, but it already had one to bonds oxygen. Okay, so how many extra bonds oxygen couldn't have? Well, we already have. We just know that the rule says you can You can Onley have four bonds, and one of them has to be a carbon. So that means that the last third bond could also be an oxygen. So what I'm gonna do here is I'm going to try to move out of the way here. I'm going to draw this molecule once again. Also as a car. Books like acid. Why? Because basically, when you're oxidizing something that has one bonds of carbon, that means it's gonna have three bonds toe oxygen. And when you have three bonds toe oxygen, you wanted to look like a carb oxalic acid. Okay. When you have to bonds toe oxygen, you want to look like a key tone. And then we have one bonds oxygen. You wanted to look like an alcohol, which is the one that I have up there. Okay, Bueno. Pretty good. Awesome. So now what I want to do is I want to show you guys another re agent. It turns out that even though we deal with strong oxidizing agents a lot, there's also a regent that's called a week oxidizing agent. Okay, now, week oxidizing agent would simply be one that doesn't oxidized multiple times. Okay, Um, the way that we're gonna define it in particular is that it can Onley add one equivalent of oxygen to primary alcohols. That's really the only difference. So what that means is that it's going to do the same thing as all the other re agents Camel for chromium six. Same thing, except in one situation in a primary alcohol. Instead of going all the way to carve oxalic acid, it's gonna It's gonna go one equivalent instead of two equivalents of oxygen. So let me show you what that looks like. Okay, So PCC is the name of this re agent, and it is our week oxidizing agent. So would it be ableto oxidize my secondary alcohol? Absolutely. It's going to do the same exact thing. So for PCC. I would get the same exact reagent here or the same exact product. Okay. Would it be ableto oxidize number two? No, nothing can oxidize number two. It's still no reaction. Okay. Would it be ableto oxidize number three? Yes, it would, but this is our special situation. Notice that I have a primary alcohol. Okay, whenever you have a primary alcohol, what that means is that for a strong oxidizing agent, I would have taken it to a carb oxalic acid like this, but for a week oxidizing Agent PCC, I'm gonna go to an alga hide instead. So that means that I'm actually gonna draw this thing like this with an H instead of an O. H. Okay, that's the biggest difference here. That's actually the Onley major difference that we have with PCC is that instead of getting carb oxalic acid, we get an alga hide. Okay, now you might be wondering, Johnny, What do you mean by one equivalent of oxygen? All I mean is that notice that at the beginning how maney bonds oxygen Did we have We had one. I'm just gonna say 10 okay. At the end of the strong oxidation. How Maney did we have bonds to oxygen? We had 330 okay. So that means that if we had one oxygen to begin with and three to end with, we added two equivalent of oxygen. Okay, well, for PCC instead of using doing to equipments of oxygen Now, we're only gonna add one equivalent, because now we have two buns to O instead of one, which is what it started with. So if you're starting with one, and yet with two, that means you only added one equivalent of oxygen. And that's what this definition has to do with. Okay, But if you want to remember, just say that primary alcohols go to Aldo hides. That's another way of saying it. That's maybe less complicated. And that's always right. Okay. You could just say it like that the rest of your life if you want to, and that's fine. Okay, let's get down to our last structure. Would it be ableto oxidize my four. Okay. And the answer is no. This would be no reaction. Why is that? Well, because it's already an alga hide. Okay, notice that Alba hide is the product of PCC, right? PCC is gonna make an alga hide. So if we haven't alga had already isn't gonna do anything to it. No. Okay, so once it's now the height, it's not gonna oxidize it more. This would be no reaction as well. Okay, So just trying to show you guys the difference between PCC and the other oxidizing agents. It's not that hard. It's just a few details you have tow. Keep in mind. All right, so that said, let's go ahead and move on.
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Problem

Provide the major product for the following oxidation reaction. 

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Problem

Provide the major product for the following oxidation reaction. 

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Problem

Provide the major product for the following oxidation reaction. 

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Problem

 Provide the major product for the following oxidation reaction.

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Problem

Determine the major product for the following reaction. 

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Problem

Determine the major product for the following reaction. 

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Problem

Provide the necessary reagents for the following transformation.

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