Show how you would make the following ethers, using only simpl...

Question

Show how you would make the following ethers, using only simple alcohols and any needed reagents as your starting materials.

(a) 1-methoxybutane

(b) 2-ethoxy-2-methylpropane

(c) benzyl cyclopentyl ether

Accepted Answer

Everyone. And welcome back in today's video, we are going to tackle the following problem show how to synthesize each ether shown below using simple alcohol as the starting material. Number 11 meth oxy propane, number two, Tuma Toxie to metal propane. And number three, Benzel psycho Hexcel Ether. Now let's just draw these structures starting with number one one meth oxy propane, we can draw a propane chain three carbon atoms. Then at carbon number one, we have a meth oxy groups. We're going to add O C three. That's our final product for one for reaction number two to meth oxy two methyl propane, right? So we can throw a propane once again, 123 carbon atoms. Position number two has a methyl group and a meth oxy group. So O C street, that's our product for number two and reaction number three produces Benzel cycle, Hexcel Ether. Now we can draw a cycle Hexcel substitution. That will be our sixth member Dring, right? We have our psycho Hexcel substitution which is bonded to Benzel Ether. So we can immediately add our oxygen atom and draw a Benzel group. So that would be sieged too. And then we have our benzene ring, we can just abbreviate that S Ph right. Ph CS two are basically C six H five ch two group. That's our Benzel group. Okay. So we see our three products, we just want to break them into corresponding alcohols. We always want to break them with respect to the position of oxygen. So we identify where our oxygen is, we will be able to produce our potential alcohols. If we look at the first one, we can think of to alcohols as one of them being professional, right? 123 carbon atoms on the left. So that would be proportional as our first possible, starting with cereal. So we may use propranolol and on the right, we only have one carbon atom. So the other alcohol we could use would be methanol C H. Similarly, if we think about the cleavage of the bond indicated here, we can troll cheap potential alcohols, right? So one of them would be Terror two Beats. No, we may try it. Now, essentially that would be our Starting material. 3rd bits. No. And the other one is once again, must will ride because we only end up with one carbon atom so that we see 30 H And for the last one we can break it apart and we will get to alcohol cyclo hexagonal on the left right, we only have our ring and then Benzel alcohol, Ph C T O H So we have our starting alcohols. We just need to think about the possible synthesis plan. Now recall that according to the Williams on ether synthesis, Because the reaction falls an sn two pathway, we want to have a primary substrate. So when we think about our alcohols, we are going to turn one of our alcohol since a primary substrate that has a good leaving group and the other alcohol would be our nuclear file. Okay. So starting with reaction number one, we can essentially use propranolol and we can make it our primary substrate very easily. We call that. We can essentially use puzzle chloride and Caroline, which allows us to make the alcohol group a good leaving group which is tha Celester. So we get our thoughts late. That'll be O T S and this is a very good leaving group and this is a very common reaction whenever we want to turn an alcohol into a very good leaving group. Now, when we get our Taza Lester, we went to form our nuclear pile. And as we previously said, the other alcohol that we're using is methanol. So what do we want to do? We want to get rid of that acidic hydrogen forming negative charge and oxygen. And the way to do that is to add sodium to our structure, which would just displaced as hydrogen and form meth oxide. Of course, there's sodium as an iron spectator, but don't get confused. There's no actual Covalin bond riders. That electrostatic interaction. The most important part is this one where you have formed your nuclear file and that's it. You're nearly done. You have your nuclear file. There's a and listen to reaction where you're attacking your primary substrate for by the loss of the leaving group and you're getting your final products, 123 carbon atoms. Now, oxygen is bonded to carbon number three and you have a methyl group well done. We got our first product. Now, if we move on to the next reaction, we already know what to alcohols, we are going to use. One of them is third beaten all. And another one is once again, methanol because we cannot form a primary substrate out of the first alcohol. We actually want to form a substrate out of methanol because that would be primary substrate. So we are going to start with the bottom part and we are going to say that she to turn it into a substrate, we want to get rid of this hydrogen. We want to turn it into a good leaving group. And to be even more accurate, we want to replace the alcohol group with a blooming Adam perhaps or a halogen that would correspond to a good leaving group bonded to carbon, right? And one of the ways to do that is to use phosphorus try bromide PBR three recall that whenever you're treating an alcohol with phosphorous tri bromide, you're essentially converting your alcohol group into and al kill hey light in this case, right, we would turn it into methyl bromide. So we got our methyl bromide and we see that this is definitely our substrate. Now, we want to form a nuclear file out of the first alcohol. And to do that, we can use the previously utilized logic where we said, what if we just use sodium, which would displace that acidic hydrogen and form our elk oxide, which is now a good nuclear file, right? So we have formed our nuclear file and we're ready to go the negative charge on our nuclear file would attack the electrical position of the substrate. And if we draw it More neatly, that would be a three CBR followed by the loss of the leaving group, we get our final product. So we made through it. Now that would be how were, Let's see, 1, 2, 3. So we have our groups and now we are going to attach oxygen bond etc that metal group. So let's see if that's what we are supposed to get. Yep, that's our alcohol. That's our ether, my apologies. So we got what we wanted for reaction number two, we may label this is our final answer. Our final synthesis for # two. And now we are ready to move on for the final reaction. Number three, we have our two alcohols. One of them is Benzel alcohol and the other one is cyclo hexane. All you may already understand what we're trying to achieve. We want to find which of the two alcohols can be turned into a primary substrate. And you can clearly see that the alcohol group responded to a primary carbon over here. So we're going with this alcohol which is banned alcohol and we are going to turn it into a primary substrate once again to do that, you're going to use Tassel Chloride in paradigm because when you do that, you're going to replace your hygiene with a tussle group, which will be a good leaving group corresponding to you're substrate O T S. So you have your substrate. Now you're going to think about the formation of the nuclear file. And once again, we have acidic hydrogen. If you have a civic hygiene, you're going to use sodium to displace it and form the elk oxide and iron consistent with a strong nuclear file. So now you're getting your Elcock sign. Once again, sodium is an ion spectator. Don't worry about it just to be completely consistent. But the main part is the presence of Alcock side itself, which acts as a nuclear file. We have an essence, a reaction nuclear attack at the Electra Philip position, followed by the loss of the leaving group. And this gives us our final product, which is our ether. So we are going to draw our Six member ring with oxygen bonded to CH two and that CH two responded to the final ring. So we got our reactions. Well done. We have all of the required reactions for this problem and we may simply conclude that the correct answer choice to the small pool choice question is B however, if you have any questions, don't hesitate to leave your comment down below in the comments section. And thank you for watching.

Show how you would make the following ethers, using only simple alcohols and any needed reagents as your starting materials.
(a) 1-methoxybutane
(b) 2-ethoxy-2-methylpropane
(c) benzyl cyclopentyl ether

Key Concepts

Ethers and Their Formation

Williamson Ether Synthesis

Reactivity of Alcohols

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