Explain why the acid-catalyzed condensation is a poor method f...

Question

Explain why the acid-catalyzed condensation is a poor method for the synthesis of an unsymmetrical ether such as ethyl methyl ether, CH₃CH₂-O-CH₃.

Accepted Answer

Hey, everyone and welcome back in today's today, we are going to tackle the following problem. Acid catalyzed condensation is impractical for the synthesis of the un symmetrical ether. Shown below. Explain why this is true isopropyl isopropyl ether. So if we draw that structure, it's already given, we have oxygen. On the left side, we are going to draw an isopropyl group. And on the right, we are going to draw a proposed group. So that's 12 three Carbon Atoms, Right. So this is the structure that we want to synthesize using condensation. And to think about condensation, we want to identify two alcohols that make death either to make that easier, we can essentially break it apart with respect to oxygen and we will get to alcohol chains. One of them is an isopropyl group and another one is a proposal group. So what we're going to do now we're going to add our alcohol groups. So here we have our isopropyl and we are just bonding O H, right? And now the remaining part is 123 carbon atoms with O H bond. It's at 1230 H. So these are the two alcohols that participate in our condensation mechanism to produce that ether. Now, let's see why this is actually impractical. If we think about the acid catalyzed condensation, we control our first possibility of this reaction, suppose that we are thinking about our isopropyl alcohol reacting with propranolol. And suppose that because it's an asset capitalized condensation, we can already protein ate one of them. So we can protein eight propranolol. This product comes from the asset. And during the mechanism, as you recall, the lone pair on oxygen here attacks the electrolytic position for by the loss of the leaving group. And then we are deep rotating that hydrogen to get our final ether. And this is indeed how we get the required isopropyl isopropyl ether. And that looks quite good for us. But what are the other possibilities? Because the mixture contains a lot of molecules of each alcohol. There's also a possibility four isopropyl alcohol to undergo condensation with itself. What if two molecules of isopropyl alcohol reacts together supposed to be protein? It one of them once again. So according to the mechanism, the lone pair on oxygen will attack the Electra Phillip position, followed by the loss of the leaving group. We are removing the proton from this part and we are getting another product, oxygen di isopropyl ether. That's what it is, right? Because we have two isopropyl groups bonded to oxygen. So there's a possibility for another product and that's not it yet. What if we think about professional. Now, because the mixture contains a lot of proposal molecules, there's of course, a chance for two propane, all molecules undergo condensation with each other. So let's suppose that we protein 81 of them. And then according to the mechanism, the lone pair on oxygen would attack that electra position followed by the loss of the leaving group. We are going to deep protein eight this part and we are going to get die proposal ether, we can just draw it okay. So now looking at these, we understand that we have a mixture of three products. Number one, number two, number three, And the only product that we went to isolate this product. Number one. Now we may say that the reason why it's impractical Is as follows. # one we get a mixture of products as you know, whenever you're getting a mixture of products and you only desire to get one single product that you're interested. And it's of course impractical because the yield of your product will not be satisfactory, right? So this is one of the major reasons. Number two, even if that's not the case, and you're not worried about the yield so much, the three ethers have similar molecular weight. So the products half similar boiling points and because they have similar boiling points, that implies that it is difficult, two separate product number one from the mixture. Now, that's these are our major reasons. We can say that the reason why it's impractical to synthesize the required either Using the acid catalyzed condensation mechanism is because we get a mixture of three products. And even though if it's not really a problem for us, the isolation of product #1 would be difficult. If they have some boiling points, we cannot really efficiently separate that product from the mixture because the products must correspond to a significant difference in their boiling points for a good separation using the distillation, right. However, if we actually want to synthesize that ether, we can have an alternative, we can use Williams on Ether synthesis. That would be our solution. And keep in mind that giving you an idea whenever we want to use condensation, we always want to make sure that we use one type of alcohol only in our solutions. So if we think about the condensation of isopropanol or professional, these are perfectly fine. If we have a solution of any of these alcohols only, then yes, that works for us because that's our single product. But if we have two different alcohols, as you can see, we have three possibilities for products and it's very difficult to separate the required one. And that would be it the correct answer choice for this question would be be the acid catalyzed condensation produces a mixture of ethers with similar boiling points which makes it difficult to isolate the desired product. I hope you found this helpful. But if you have any questions. Don't have States leave your comment down below in the comments section and thank you for watching.

Explain why the acid-catalyzed condensation is a poor method for the synthesis of an unsymmetrical ether such as ethyl methyl ether, CH₃CH₂-O-CH₃.

Key Concepts

Acid-Catalyzed Condensation

Unsymmetrical Ethers

Selectivity in Organic Reactions

Watch next

Explain why the acid-catalyzed condensation is a poor method for the synthesis of an unsymmetrical ether such as ethyl methyl ether, CH3CH2-O-CH3.

Key Concepts

Acid-Catalyzed Condensation

Unsymmetrical Ethers

Selectivity in Organic Reactions

Watch next

Explain why the acid-catalyzed condensation is a poor method for the synthesis of an unsymmetrical ether such as ethyl methyl ether, CH₃CH₂-O-CH₃.