Predict the major products of the following reactions.
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Question

Predict the major products of the following reactions.

d. trans-cyclodecene + peroxyacetic acid in acidic water

e. cis-cyclodecene + mCPBA in CH₂Cl₂, then dilute aqueous acid

Accepted Answer

Hey everyone and welcome back into this video. We are going to tackle the following problem, examine the following reactions and predicts the major products. If we look at the two reactions. Given we notice that we are starting with two Al kim's. One is a trans Elkin right? Because that ring has to alcohol submissions on opposite sides of the double bonds. We may say that this is a trans al king and this one is this right? Based on the same reasons, simply speaking, the two alcohol groups are pointing down in the same direction. However, they both contain eight carbon atoms, so they are both cyclo octane molecules. The main difference is that for reaction a we're using a different set of regions. Now, if we examine a to begin with, we may simply redraw our substrate. This is our L king and we understand that the first reaction is the addition of parasitic asset. Notice how there are three oxygen atoms here. C 00 H c 03 H implies that such an acid is a proxy asset. So if we remember that when al kins are treated with proxy assets, we are forming epoxy sides will be good with that understanding that the first step is the formation of an epoxy because we're creating an alkaline with parasitic assets. We're just going to form an epoxy at that position and essentially what we want to do. We want to stay that adding parasitic assets. Ch three C 03 H in the first step that forms and keep oxide. Now there are two ways to form any box that we are going to form a three member ring with oxygen here. Right, we're going to break that double bond. We may either place oxygen on two wedges or two dashes. That's perfectly fine. We're only going to look at one of the two structures. So having added oxygen above the plane of the rain on two wedges, we now have to think about our next step. And our next step is the acidic hydrolyzed stop recall that during the yesterday hydraulics is that's our reaction number two. We are protein eating that oxygen. So if we protein ate it, we are forming a protein ated intermediate when this protein ated intermediate is formed. And since we have the loss of the leaving group, what are here? Right. We removed one of the protons from hydro knee. Um Now we have a water molecule because the conditions are acidic. You may wish to remember that the nuclear attack will take place at a more substituted position there to electra Philip carbon atoms but they're equally substituted. And that essentially implies that any of the two positions can be attacked. If we attack that position, we will form one product. If we attack this position will form another product there will be a pair of finance humors. So let's see how that works. If we attack that position. Remember that this is a backside attack. So we will have an inversion of configuration at that center followed by the loss of the leaving group. And after the deep protein nation stop of that H20 molecule, right? Because it's going to form another bond. Carbon oxygen bond. We will have an excess of protons. We will be able to remove one of the acidic hydrogen. We will see that we are forming a dial one comma to dial. So we will have two alcohol groups adjacent to each other. Now, as we previously said at this position, a wage will be pointing down because we have an inversion of configuration and at the adjacent position the alcohol group will be pointing up. So we have that and the arrangement of the two substations when we're looking at the trans version. So this is pretty much our product but we can move forward and essentially rotate the carbon carbon bonds so that instead of having trans positions, we will only end up with six positions in our ring. We may essentially redraw our ring normally with only six positions. And if we perform that rotation, one of the alcohol groups will change its orientation in particular. If we rotate that bond, we will understand it. Instead of having a dash bond, we will have a wedge bond. So we may now perform that rotation and draw our eight member dring. So that's our eight member ring and we are going to add two alcohol groups in similar arrangement. Now, right because we're going to add them to a cis bond, right, essentially. That's not really correct to state. But if you look at the two alcohol groups and imagine if there was a double bond at this position that we exist Elkin. So now, essentially because we're rotating that bond, the two alcohol groups will be pointing up or down. So we have one of our alcohols, this will be one comma two dial plus. It's an antenna as we discussed before because there are two possible ways to attack it. We are going to form an N. And more of that structure as well. But it's really important to understand that this structure is not Kyle because there's an internal plane of symmetry. So we can say that there will be no N. And this is a miso compound. Right? So this is our product for reaction A and we may just label this. It's our final product for a. Now if we move on to be, we noticed that we have a similar reaction. So lets redraw it and let's analyze it now for B. We are going to redraw our eight members rain. We understand that we have our double bond in this position and the first reaction is the addition of Em CPB a right addition of Em CPB A, which is meta chloral peroxide boric acid. Also in ch two cl two die chloral methane. That's our solvent. We have a word step to what we had before. Em CPB is just another proxy acid. So it will form an epoxy at that position, meaning we may simply draw an ip oxide formed. So instead of having a double bond at this position we will just have any pox side. Again, we're choosing to add it above the plane of the ring. So that will be our dip oxide. And now in the next step we're performing an acidic hi trolley sis we already know how that takes place. So we will think about it this way we are protein eating that oxygen to make it a good leaving group. And then the water molecule attacks any of the two positions because they are equally substituted general we attack the one that is more substituted because conditions are acidic. But in this case we may attack any of the two positions to possibly form a pair of financial works. So if we attack this position we will have the loss of the leaving group which will be oh age, meaning we may just draw our ring first and then perform that analysis. So that would be our eight member grain. And now we understand that if we attack this carbon atom, right, we are going to reverse the configuration at it because that's the backside attack. And during the backside attack, we are performing an inversion of configuration. So instead of having a wedge, we will have a dash here for our first alcohol group. And during the loss of the leaving group there will be another alcohol group which will have exactly the same orientation in space regarding its bonding, right? Carbon oxygen bond will be pointing up so that will be our second alcohol group. And we can say we are forming a pair of finance us because there are two possibilities to attack it. And because the structure is not miso, it doesn't have any internal line of symmetry. We may say that a pair of financial versus form. So that would be our second product and we will just label it as product B. Now, let's analyze what we got. So for the first reaction, because we started with a trans AL King, we perform an iP oxidation reaction, followed by the acidic hydrolyzed this and we obtained a sundial, right, which is a miso structure. So one comma two dial here is a means of structure because there is an internal line of symmetry. While for B. Because we started with assist Al King, we actually formed a one comma two trans dial, in which the two alcohol groups are pointing in opposite directions. That's why we have a pair of finance farmers here. And now, to conclude the correct answer to this multiple choice question is B However, if you have any questions, don't hesitate to leave a comment down below in the comment section and thank you for watching

Predict the major products of the following reactions.
d. trans-cyclodecene + peroxyacetic acid in acidic water
e. cis-cyclodecene + mCPBA in CH₂Cl₂, then dilute aqueous acid

Key Concepts

Electrophilic Addition Reactions

Peracid Reactions

Acid-Catalyzed Hydrolysis

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