Organic Chemistry

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19. Aldehydes and Ketones:Nucleophilic Addition

Overview of Nucleophilic Addition of Solvents


Nucleophilic Addition of Solvents

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Hey, guys, In this next page, I want to give you a big picture view of how ah, lot of seemingly random Carbonell reactions are actually all related to each other. And this section is called the Nuclear Filic Edition of Solvents. So in general, all the reactions that I'm gonna show you on this page are all connected by one theme, which is that they're induced by the extra extraordinary reactivity of the carbon or carbon. Remember, it has a very strong partial positive. So strong, in fact, that that partial positive isn't just gonna react with negatively charged nuclear files. It's also going to react with solvents. And I wanna put here in parentheses, neutral solvents. So that means that the carbon eel can actually get neutral things to attack it through nuclear filic addition. How crazy is that? Well, thes reactions aren't gonna happen by themselves. They are gonna need catalyst. They're gonna need either acid or base catalysts. Okay, In general, almost all of these reactions are gonna be acid catalyzed on the mechanism we're gonna be focusing on in this section are the acid catalyzed mechanisms. Okay, Those the ones that air the most commonly tested on. Okay, um, and then one general theme about all these reactions that I'm not gonna have to say over and over again because you guys will know it is that they're all fully reversible in mild acid. So you could always use mild acid to go back to the original carbon deal that you started with. Okay, Due to the fact that these mechanisms are mostly acid catalyzed whenever you have something that's an acid catalyzed mechanism, then by definition, prote nation should be your first step and deep throat nation to regenerate, the catalyst should be your last. So when you're looking at one thes daunting mechanisms, some of them are gonna be like 12 step mechanisms. But when you look at them, at least you should know where to start. You should always think I should protein ate before I do anything else because it's an acid catalyzed mechanism. So let's go through the list. I'm really just gonna be giving you the, uh you know, just the general features here. And then we'll focus on the details in each respective reaction when I go to the reaction videos. Okay, so the first one in the easiest one guy's ketones and Aldo hides air so reactive this partial positive is so reactive that it can even get water to react with it. Okay, so when water reacts in the presence of acid with a key toner also hide. We called it a hydrate and notice that your product is basically a gem dial. So we would call this a gem Diallo or general denial. Okay, so just keep that in mind. Water. Let's just We're just starting it off with, like, the most shopping shocking solvent, which is that even water reacts with carbon eels. Toe form a gem dial's so meaning that if you have a mixture of key tones and water in your test tube, it's actually not gonna be all key tone. Some of it is gonna be gem dial because the water is reacting with it. Okay, more on that later, hammy hospitals so heavy hospitals, air produced by the addition of one equivalent of alcohol. So one equipment of alcohol will give you something called a hammy as a towel. Two equivalents of alcohol. We'll give you an A Seattle. Okay, So, Hemi Estelle, a subtle notice. The difference is that one of them has an O H. Group, and one of them has an O R group. So basically, in one of them, you're only adding 10 r from alcohol. In the second one, you're adding to O. R s from two alcohol's. Okay. And guys, the name Hemi Hospital means half oven a settle. Because Hemi is a prefix, that means half like hemisphere, half of the world. Okay, so then we've got Theo s hotels owned by the way, guys, these can happen in both both acid and cat and based catalyzed reactions. But I'm just gonna focus on I'm just gonna focus on the re agents right now. And then we'll talk about the mechanisms. Like I said in separate videos. So, Theo, hospitals happen when you mix BF three with s, our or I should have put it the other way. Um, with basically h s r r s h, there we go. That's what I'm looking for. So instead of and alcohol notice that it's the same thing as an alcohol. But instead of being an alcohol, it's gonna be a file group. Okay, So our s h times two groups R S H times too. Okay, So notice that this reaction is actually very similar to the one above it, As telling Theo has to tell, The only difference is that now getting s age groups instead of, oh, age groups because I'm reacting instead of our wage, it's R S H. That's it. And then the acid here, in this case, is just a little special to be F three instead of your normal Braun said Lowry acid. Okay, cool. Let's keep going. So what happens if you react a means with carbon eels? Well, it turns out that primary means so if I have N h two are primary means so primary means will give you an Emmy in product. Okay, so this functional group is called an m mean Alright, it's a double bond. And within our group at the top. Ok, now this also works for ammonia or NH three. Okay, Primary means or NH three is going to give you an Indian. Okay, now, on top of that, if we react with instead of NH to our if instead we add instead of in our group we had something else. Like for example, ah z group. Now that Z could equal a few different things that Z could be, you know, another nitrogen. It could be an alcohol etcetera. Okay, so there's a lot of different things that we could put there. Okay, but if you add something else instead of that are then you're going to get an Emmy and derivative because instead of getting the are at the top, OK, now, notice This are is what's attached here. Now you're gonna get a Z instead. Okay? Makes sense. So that would be what we call an Indian derivative because of the fact that it looks like Indian. But instead of having an art group that has a Z group on finally, we know what happens when you after NH three. What happens when you have a primary means? What about secondary means? Well, when you have secondary means, Um, so that would be n h with to our groups, are are. Then you get what's called an enemy. Okay? The reason this is called an enemy mean is because you got in the main part of the top and you've got a double bond on alki so put together, you get an enemy. Okay, so now instead of just having one our group attached, you have to now notice that the orientation of this dull bond is really different than the first one In the mean the dull bond was facing, the end was on the end in the second one. The double bond is now towards the carbon. Why is that? Well, that's something that we're gonna have to learn through the mechanism. So when we go to the exact mechanisms, you'll understand. But it's It's essentially the same exact mechanism, just with one final step. That's different. Okay, that's the biggest difference between them. All right, so that is pretty much the extent of the reactions of solvents with ketones and alcohols and notice. I pretty much named every single solvent that's out there. I mentioned water. I mentioned alcohol and every form I mentioned Thile. And now I mentioned a means all types of means. So if it has a lone pair, it can react with the carbon meal. Okay, Now, what I wanted to is I want to just really briefly introduce what can happen with these re agents. So after you make them, what can you do with them? Well, it turns out that heavy hospitals as well learn later, are not very stable. They like to go to full asset towels so they barely ever lasted 10 hospitals. Onley, cyclic Hemi hospitals are stable. Okay, so we'll see that later. So this would be a cyclic mes. It'll cause notice that I've got a carbon that's attached to, um, you know, it's gotten it's gotten age. It's got a R and then it's got the O. R. Here, and it's got the O. H. Here, so that would be a Hemi as a towel. And we're gonna have to learn how to recognize thes. But that would be a heavy as a towel, because I've got a carbon in the middle that has an O. R and an O. H group on two different sides, and this one would actually be stable. But if it's not sick like it's not gonna be stable as hotels are used as protecting groups. Okay, so as to tell specifically when you have a dialogue, you get cyclic protecting groups. So that is how this thing is a ring. Okay, so we're gonna see how later on when we use Dial's, um instead of two different alcohol. When you dial, you get a cyclic as a towel. And in general, a settles are used as protecting groups. So more on that in another video, who so what happens with what can you do with the Theo's to tell? Well, remember that if I was to tell is just a molecule that has a central carbon with ours, and both sides are their ages and to SHS to files at the top. Well, it turns out that when you react a thigh also tell with the reducing agent called Raney Nickel Raney, nickel Raney Nickel is gonna be able to destroy those Thile bonds and make it into a simple al cane. So it's a form of reduction that turns essentially training a carbon eel into an al cane because you're just adding ages, so it's a way of getting rid of carbon nails completely. Okay, it means derivatives. So it turns out that it mean derivatives when you have specifically, if I were to use the NH two z okay, so specifically, if I were toe have this derivative more on that later, that's called Hydro Zone will talk specifically about that later number This is just the overview. But when you react hydro zone with a strong base and heat, you get what's called a wolf Kitchener reduction wolf Kissner reduction. And what we find is that a wolf Kitchener reduction is another way. Toe ad hydrogen to carbon eel. So it's another way to turn a carbon Neil into an al cane. So Raney nickel to a Theo hospital wolf Kissner to a hydro zone which is in the main derivative are really the same reaction in terms of they build the same exact products and they're used in very similar situations, except one is based catalyzed, and one is acid catalyzed because you're gonna have to use that BF three to get the thigh lost a towel. Awesome. And then finally guys, this is kind of getting way ahead of ourselves. But it turns out that any means we're gonna find out later, Love to react with alcohol. Hey, lied. Okay? They love to react with alcohol. Hey, lids, toe form What we call Alfa substituted carbon eels. So essentially I mean this reaction we'll talk about it more in the Inamine calculation section of clutch videos. But essentially you get a lone pair that jumps down. Ah, double bond that attacks the are basically doesn't s into reaction, and you end up getting our group where that enemy WAAS. Okay, so this is ah, huge part of organic chemistry all on its own Is just talking about how any means love to react with al Kyohei lights and other types of electric files to get Alfa substitution. Okay, so, guys, I know this was overwhelming, and to some extent, it's meant to be. What I'm trying to show you is that all these reactions, you're gonna learn them in different parts of the text, but they're all related by the sense of that. It's a neutral compound, reacting with a very highly positively charged Carbonneau carbon. Okay, so now what we're gonna do is now that you've seen the overview, we're gonna go into those individual reactions one by one, and we're gonna learn mechanisms. It's gonna be fun. All right, so let's go ahead and wrap up this topic and start onto the next topic