Give structures of the alkenes that would give the following p...

Question

Give structures of the alkenes that would give the following products upon ozonolysis–reduction.

(a)

Accepted Answer

everyone and welcome back in today's video, we are going to look at the following problem, predicted the al keen that would yield the following products when treated with ozone and the muscle sulfide. If you look at our structure, we understand that this is a diet ketone, right? Because it has two carbonell groups. We have a carbon group at that position and then there is another carbonell group over here. So this is a die key tone. It has two carbonell groups with alcohol substitutes surrounding it. So we understand that it must be a dikky zone. Now let's recall what cyanosis is because that's the major focus of that problem. We wish to predict an alkaline. So some unknown structure acts undergoing the reaction of Los Angeles is number one, we're adding ozone just as the problem suggests. So that's oh three at a low temperature, generally negative 78 degrees Celsius. That's what you may expect to see. And number two dimethyl sulfide. That BME two s indicating the presence of dimethyl sulfide. In the next step, during the analysis of al keane's, we're breaking the carbon carbon double bond and we actually have two cases, we wish to recall these two cases in particular if you have A straight chain. Al cane wet substitutions are one R. T. R three and let's suppose instead of an L kill suspicion you have hydrogen disposition if you perform Osnos is on that molecule always on followed by dimethyl sulfide. You will essentially break the carbon carbon double bond and you will add oxygen atom to each end. What we mean by that is simply you made sure that broken double bond at your substitutions are one on the left as well as our two. Then for the remaining part you will have our three and hygiene. So as you see, we have broken that double bond. What we're going to do now, we're just going to add oxygen atom to each to form two carbon compounds. So you noticed that here we get a ketone For the next one. We get an al to hide. This is the general those noses reaction, which tells us that the reaction is very simple. Just break the double bond, add oxygen to each end of the result of double bonds. Now the problem with this exercise is that we only have one structure and we have to recall that if we get only one carbonell compound, it must imply that the double bond exists within a ring. So let's suppose if you think about any general ring, let's suppose just cycle vaccine. Right. Nothing really changes. We're breaking that double bond and we're adding oxygen to each and of the results of double bonds. So if we draw that general model, that will be helpful for our problem. I was on full of by dimethyl sulfide, we will have the ring opening. That's why we're not forming two different compounds were breaking that bond but we still have these carbon carbon bonds presents. We're just opening our ring. And what we can do, we can essentially label our carbon atoms for simplicity. Suppose that we start from here 12345 and six right? We have six carbon atoms and we may draw a six member chain because we're breaking that bond. So that'd be 123456. Position number one now has a double bond because we have broken it and position number six also has a double bond. So that's 123456. There's another double bond at that position. Now we have broken the double bond, we have opened the ring. We have to recall the previous stuff. We just need to add these two oxygen atoms and we are done. We understand that we got and all the hydride there to al to hide groups. There are hydrogen atoms. We just haven't shown them. But if you look at them in particular here we have two hydrogen atoms, that's where they come from. So using this model, we are going to think about this problem pretty much in the same manner. These two carbon steel groups should have come from the same double bonds. We're going to fuse them. In other words, we're going to remove these oxygen atoms. We're going to just forget about these t oxygen atoms and we are going to fuse these two double bonds into a single double bond to create our ring and then we will check if our assumption is right? So what we're going to do, we are going to essentially label our carbon atoms and we are going to do it this way because the little bond exists in the ring. As we previously explained, we understand that we may start with position number one at this carbon atom and then we will stop at this carbon atom because that would form our ring and the other substitutions would be outside of the ring. So that be carbon number 1234, five and six. Right, we stop here because we are fusing these bonds together. You may think about the bond rotation and then you can think about, you know, basically overlapping them. Now, however, we understand that this is a six member ring. So let's draw a six member ring just as with it before. Now, if we enumerated for simplicity, that would be one, two, three, 4, 5 and six. We are combining the double bonds of position one and six. We call that there are no more oxygen atoms. We're just making a a basically one double bond. Right? So between carbons one and six were forming a double bonds. We may add that double bond and we understand that position number one also has a metal group attached to it. So we're going to add that metal group In position # six has another method group at Ash sets. We are adding another method group. So this is our possible answer. Now, let's check if that works for us. If we essentially use the idea of those analysis. We may simply say that if we perform ozone noses on that Al King, that had been number one ozone at lower temperature, number two. Their muscle sulfide. Now, as we understand from the previous model, we're just breaking this carbon carbon double bond and we're opening our ring, right? So we will have a six member chain of course with two metal substitutions, we may destroy six member chain 123456. Now, position number one has a metal substitution. So we're also going to add a metal group In position # six also has a metal group. So we're going to add it, position number one as a double bond. After we break that double bond, position number one has a double bond and position number six has a double bond, right? We're breaking it and we have an equal sharing of that remaining double bond. So there will be double bond here and here. In other words, these are positions one and six. And now based on the fact that this is an ozone knows this reaction. We're simply adding an oxygen atom to each end and indeed, this is our diet ketone meaning this structure works for us and we may say that, okay, this is our final answer. This is our possible al came for this reaction. Now the correct answer choice to this multiple choice question is C. However, if you have any questions, don't hesitate to leave your comment down below in the comment section and thank you for watching.

Give structures of the alkenes that would give the following products upon ozonolysis–reduction.
(a)

Key Concepts

Ozonolysis

Alkenes

Reduction Reactions

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