Show how you would make the following compounds from a suitabl...

Question

Show how you would make the following compounds from a suitable cyclic alkene.

(a)

Accepted Answer

Hey everyone and welcome back in today's video, we are going to show the complete reaction for the formation of the given molecule. Starting with a suitable site, click al king If we analyze our target molecule because that's what we want to synthesize. We understand several facts. Number one, this is a dial because carbon is number one and two. They contain two alcohol groups. So we can call this one comma to dial Act No two. Is that if we analyze stereo chemistry, the two alcohol groups are pointing in opposite directions with respect to the plane of the ring, one of them is pointing up. Another one is pointing down so we can say that they have anti arrangement. Number three. We want to propose a cyclic out scheme and because we have a ring in our molecule itself, the target molecule has that ring. So it makes sense to propose cyclone fencing as our starting material and we are going to add a double bond at any position that we want. However, it's worth noticing that there are two metal substitutes. Right? One of them is over here and another one is over here. So we are also going to add these two metal group. So this is our possible material Number four. We have to conclude that because we are starting with a cyclic alkaline and we are forming a dial. We are going to perform die hydroxy elation. We call that whenever we're using al canes and we're performing that hydroxy elation. We're going to add two alcohol groups across the double bond by breaking that original pi bond right now there are several ways to do that and it really depends on the stereo chemistry because the arrangement of the two alcohol groups is anti. We want to use a proxy asset a proxy asset as opposed to something like osmium tetroxide or potassium permanganate. But actually give us that anti arrangement desire. So that's really important. We want to use a proxy acid and that's what we conclude from here. And what kind of acid do we know? We can use em CPB a. We can use parasitic asset. And for the purposes of this problem, let's stick with parasitic asset which has a form of CH three C 03 H. That would be parasitic asset. Let's keep in mind that the first step will not necessarily be the formation of the dial itself. We will be forming an ip oxide intermediate and then the next step would be acidic. High troll is us to make sure that we're opening that epoxy in and finally forming our dial. So let's take all of these four steps into account and see what we got. So if we start with our cyclic al king, we are going to draw our five member ring with a double bond to method groups. And as we suggested, the first step would be the addition of parasitic asset. Let's label this is our first region CH three C H. Parasitic asset essentially immediately forms any box side here. So as we previous assad number one is the epoxy intermediate that we form and we can throw the result on the box side. So that's our five member going now. The two metal groups will be on the same side. Right? We are going to draw two wedges or two dashes. It's not really relevant as long as they're on the same side, you're good. And then we are adding oxygen to form that the box side ring. So we got our inbox side intermediate. And as we previously suggest that we want to perform an acidic hydrolyzed sis to open that ring and form our dial. So we're using H plus in the presence of H two. Remember that? The first step is the Protein Nation steps. So the lone pair on oxygen gets protein ated, we get our protein ated intermediate. And now the next step is a new clip like a text up now what I can attack any of the two positions. Keep in mind that during the acidic ring opening of the box sides, the new valve would attack a more substituted position. But because these two electro carbon atoms are equal as substitute at any of the two positions can be attacked. So if we attack this position, we essentially have a backside attack. And this is why the arrangement is anti right during the backseat attack, we would have an inversion of configuration here, followed by the loss of the leaving group. And this is how we are forming our first product. So we may simply indicate that we are obtaining our first product and if we draw it starting with that five member ring, we understand that nothing changes regarding configuration at that position because it's the leaving group that is bonded said. But here we have an inversion of configuration but we will also need to d. Protein ate the resulting molecule of water that is now bonded to carbon to make sure that it's an alcohol group. And this alcohol group will now be pointing out inversion of configuration right? And then the metal group will now be pointing down but keep in mind that we are also forming an anti armor. What if we attack this position which is also equally substituted compared to the other one. We have another backside attack followed by the loss of the leaving group and we are forming an an and humor. So if we draw that we understand that we have an inversion of configuration at that position. So there will be an O. H. Pointing out method group pointing down and here nothing changes. The metal group is pointing out and the alcohol group is pointing down even though only one of the two products is shown, it doesn't really matter. We just showed that in addition to that product. If we suggest this to be our pathway, we are actually forming two products in roughly equal quantities right? Because this is a systemic mixture. The probability of attacking any of the two carbons is pretty much the same. So air ischemic mixture of finance commerce is formed. So this is our complete pathway. We can just conclude that the regions that we need for this transformation are the following ones. Number one. Or we can simply just draw it out right. We can say that we are suggesting our cyclic elkin and we have to treat it with several regions. # one would be addition of parasitic acid. Number two would be acidic hydrolyzed SIS where we opened the ring of the box side. Right. And that's pretty much it. We can simply conclude that in this problem there was one intermediate which has any box side. And when a box that is formed we have that ring opening to form a pair of finance commerce that nick mixture legislate bill this as our finally answer our cyclical keen and the set of regions that we need to perform the required transformation. The correct answer to this multiple choice question is the However, If you have any questions, don't hesitate to leave a comment down below in the comment section and thank you for watching

Show how you would make the following compounds from a suitable cyclic alkene.
(a)

Key Concepts

Cyclic Alkenes

Functional Group Transformations

Stereochemistry

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