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.

(b)

Accepted Answer

Hey everyone and welcome back in today's video, we're going to look at this problem which reads show the complete reaction for the formation of the given molecule. Starting with a suitable cyclic L king. If we examine the starting material, we notice that this is cyclone. No name. One comma two dial. Right? We have a dial. And in particular the problem asks us to propose an AL king for our synthesis. If we are starting with an alkaline And if we wish to produce a 1:02 dial, we wish to recall a di hydroxy elation reaction. We may have two types of di hydroxy elation depending on stereo chemistry. There are two cases. One of them is sin and the other one is anti. Look at the structure in particular. What we want to do. We want to break these C. O. H bonds right? We want to get rid of them so that we can propose an elk in. That would work for us for either sin or ansi di hydroxy elation. If we break these groups apart and if we replace them with a double bond, we will be able to perform an oxidation to form an IPAq side and then to form that dial. So let's see how that happens. What if we just break them and place a double bond at this position, which would make the two alcohol groups point in the same direction. So we would have our first case A where we simply break these bonds. We re troll our nine member grain. So that's our nine member ring. And we have two possibilities to place a double bond in that we may either choose this as our position to make it a cyst Elkin. Right, remember that eight member rings or larger? They exhibit cis trans isomerization. Or be. We may also place that double bond in a transposition. So let's suppose here. So now we can place over here. Now it's very important to understand that the structure that we are synthesizing has a plane of symmetry. If you notice there's this horizontal line and with respect to that line, one part of the molecule is symmetrical to itself. What that means is that we are forming a missile compound and we have two cases to do that. If we start with a cis L. King, we wish to perform a syn addition. If we start with a trans L. King, in that case we wish to perform an anti edition to get a missile compound. So we can look at these two cases. What if we started this, this alki and we need a region that forms a sin arrangement of the two alcohol groups. And in particular, if you recall, this reaction requires us to use osmium tetroxide in hydrogen peroxide. So this is one way to synthesize our final compound. We noticed that we have a syn addition across that double bond, we're breaking the pi bond and we're adding two alcohol groups to get our final di. Oh, so if we draw our product for this part, we noticed that indeed we get the structure that we need to get, we get two alcohol groups in sin arrangement, They're both pointing up. Right? So that's our first possibility. We may make use of this reaction and trans one requires us to use the anti addition. Now, what is the way to perform an anti addition? There are two steps. Step number one is to use a proxy asset and we may use parasitic acid C three c H followed by acidic hydra leases, we are going to use a strong asset in water. In that case we will form two alcohol groups in anti arrangement, meaning one of them will be pointing up, the other one will be pointing down if we just draw our structure. We noticed that, as we previously said, one of the alcohol groups will be pointing up And the other one will be pointing down. However, if we perform the bond rotation, just as we do with straight chain, al kill chains, we may notice that if we change our positions of the al kill groups. In other words, if we make sure that the two alcohol groups are on the same side of the carbon carbon bond, I suppose at this position or that position, we will essentially perform that bond rotation so that one of the alcohol groups will reverse its spatial arrangement. In other words in particular, if we look at this group, it will start pointing up and we will get the same structure. So if we perform that bond rotation or simply change the position of the two alcohol groups, that's supposed to this position or that position, we will get the same structure. So let's see how that looks like let's suppose we want to get them at the same position as these two groups, then we are basically getting the same structure. So now the two alcohol groups are pointing up due to the fact that once again, this bond, this carbon carbon bond had the two alcohol groups on opposite sides and this carbon carbon bond has two alcohol groups on the same side, meaning we had to change the spatial arrangement of that dash bond into a watch. So that's another way to perform that synthesis. And we may now understand that. Okay, we have two ways to synthesize our compound depending on where the double bond is. So we may say that these are the two pathways four our product in particular, we may either use is this al keen with Austrian tetroxide and hydrogen peroxide, or the trans version of the dl keen and then use parasitic assets for by acidic hydrolyzed sis and therefore we may conclude that the correct answer to this multiple choice question is b However, if you have any questions, don't have states livia 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.
(b)

Key Concepts

Cyclic Alkenes

Hydroxyl Groups

Synthesis Strategies

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