Show how you would accomplish the following conversions.

Question

c. trans-hex-3-ene to meso-hexane-3,4-diol

Accepted Answer

Hey everyone and welcome back in today's video, we are going to tackle the pulling problem, predict the regions for the following reactions. We are starting with an L. King. This is butte to in right, we have a double bond present and we are forming a dial before we propose our regions. We want to make sure that the arrangement of our carbons in space is pretty much the same to understand whether these two alcohol groups that have been added across a double bond are in sin or anti arrangement. So what we're going to do, we're essentially going to rotate at bona bit to make sure that our metal groups are pointing in the same direction. And if we do so, we understand that we have a four member chain. The first alcohol group is still pointing up, but the second one after that bond rotation is now pointing down. And this is extremely important for us to understand because now we clearly see that the two alcohol groups have been added in anti arrangement. Right? So essentially what we have, we have an anti di hydroxy elation off and al keen recall that we generally have several reactions whenever we're forming dials out of Elkins. And depending on what kind of arrangements we wish to obtain, we're choosing different sets of regions. What we can do here, we can essentially take our elkin and we can produce any pox side out of it because producing an epoxy that will allow us to get a backside attack, after which the two alcohol groups will be pointing in opposite directions, forming that anti arrangement. So why don't we just use that idea in the first step of our reaction. We may produce any pox side. Let's suppose using meta chloral peroxide, benzoate acid or any other proxy asset. For simplicity, we may take Parasitic assets. So that would be CH three C H. This is parasitic asset and it acts similarly to M. C P B. A. That we previously mentioned. Right? M C P B A. Is another region that could be used over here to produce an ip oxide. And what we're doing here, we're essentially forming an ip oxide. We may simply say that the product that we're producing here is our intermediate. Is that epoch side. So that would be our ip oxide. We are forming a cyclic structure, a three member drink here with oxygen bonded to two carbon atoms. This is our ip oxide. Now in the next step, this ip oxide formed must form the dial and to do that the world. First thing we want to do, we want to protein ate it to perform a nuclear attack later. So our next step is the protein ation stop where we are adding age plus the environment is acidic due to the presence of per asset and epoxy it can be easily protein ated to make it a good leaving group for us. So the lone pair will get protein ated. And we may say that we are producing a protein ated intermediate with a pause of charge. Now later on we need to have our nuclear file in particular. We are going to use water as our nuclear fire right? Because we need an additional O. Age group to be added whether it will attack a more substituted position. But these two positions are pretty much equivalent, right? They are equally substituted. So it doesn't really matter which one we are attacking. Let's suppose we take this one for our attack. We have a backside attack and this is why we expect to have an anti arrangement of the T. O. Age groups during the backside attack we will have an inversion of configuration of the center and then we will have the loss of the leaving group. So now we understand that if we look at our product there will be four carbon atoms at this carbon atom. We will have a wage pointing up and see to the backside attack in particular here. Oh age will be pointing down but we don't really have a wage yet. We have oh H two since we have added a water molecule. So there will be formal positive charge. And later on after the D. Protein nation step another water molecule can essentially d. Protein ate it to form our final dial where a wage it's pointing up and this one is pointing down now if we rotate our bond we indeed will see that we get our final product right. It will essentially look like this T. O. Age groups pointing up. We may also notice that this compound is um easel compound due to the fact that it has a plane of symmetry. One part of it is the reflection of theater, so it's a missile compound. But we clearly see that the route that we're taking here works for us and the set of regions that we're going to use is as follows. In particular, we are going to use number one that would be per acidic asset. However, Em CPB works as well. Just as we said before rights produced at a park side and number two, that would be additional water to make sure that we get the anti arrangement alcohol and that will be it. We may just label these as our region. Step number one parasitic assets, step number two, addition of water and the correct answer to this multiple choice question is d 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 accomplish the following conversions.
c. trans-hex-3-ene to meso-hexane-3,4-diol

Key Concepts

Alkenes and Their Reactions

Stereochemistry and Meso Compounds

Hydroxylation Reactions

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