Predict the product of ozonolysis of the triglyceride shown.

Question

Triglyceride structure with ozonolysis reaction steps, O3 and CH3SCH3, leading to product prediction.

Accepted Answer

All right. Hi, everyone. So this question is asking us what are the products when the following triglyceride undergoes Ozono sis. So let's go ahead and talk about it, right? Recall that the suffix lysis in ozono assis refers to the breakdown of something, right? So the term Ozal thesis means that an all keen is going to react with ozone to break down that ki this is why ozono assis is also referred to as oxidative cleavage. So here if we have an All Keen, right, the pi bond of the keen is going to be broken or actually let me rephrase that. What I meant here is that the two carbons of the starting double bond get separated from each other. That's a better way of describing it. So after the two carbons of the alkene are separated from each other, both of them get oxidized to produce car bals. So the reason why we describe Ozono thesis as a breakdown into smaller components is because the separation of the carbons in the starting alkene results in two different fragments or in other words, different car bono containing compounds. So the idea here is to imagine sort of imaginary lines separating all of the double bonds present in this compound. Specifically, all of the all keens present in this compound, that's going to give you a better idea as to what each fragment is going to look like. So when examining the structure provided, right, our triglyceride, we can see that there are four different carbon, carbon, double watts, right? All of those are going to be broken down and each carbon of the double bonds are going to be oxidized to create a car bal. So the first thing I'm going to do is draw these lines going through each all key to imagine those two carbons being separated. So after I've separated all of my all cans here, I can get a better idea as to how many distinct fragments there are going to be in our products, right? And so when I count, I can see that there are 123, 45 distinct fragments that we're going to see in our product or in our product side. So the main principle is this right to figure out the products of this particular Ozono thesis reaction, we're going to break each double bond and place car bono groups on each of the carbons in the original double bonds. So I'm going to go ahead and scroll down somewhat because I'm going to need a bit of space for all of these products. And I'm going to go ahead and actually move this generic reaction that I talked about in the beginning, I'm going to move it towards the top because I want to open up space for all of my fragments that works. All right. So let's go ahead and start with this first fragment on the top, left side of our triglyceride. And what I'm going to do here is I'm going to count how many carbons are in this particular fragment. So that's 1234 and five. So my first product is going to be a five carbon chain, you have five carbon chain and the carp in here in my fragment that is farthest to the right side was originally part of a double bond. So that carbon is going to be a carbonel. So that takes care of our first product. So now let's go ahead and count the number of carbons present in the second fragment. That's 1234 and five once again, actually. So our second product is another five carbon chain with a car bono at the very end as well. So now let's go ahead and tackle fragment three in the middle Frackman three includes our Glycerol and all of the ester linkages in our fatty acids. So here I'm going to first go ahead and start by copying my Glycerol backbone simply because I think that's going to make drawing this easier. So that's three carbons with oxygen on each one. So then to the very right side after the oxygen from Glycerol, we have two more carbons. One of them is the car bole from the Esther linkage. And the other was part of the starting double bond. So that one becomes a car bal as well, so far, so good. So now on the very left side, we have the same thing right after the oxygen from Glycerol, we have the carbonel from the ester linkage and we have the carbon from one of our double bonds. So this means that after that particular oxygen, we're going to have two carbel once more, I may have to move this drawing so far, so good. So now let's start with the oxygen here in the center of our Glycerol backbone. In this case, we have, after the oxygen, we have a four carbon chain, one of which was the carbel of the Esther linkage. And on the third position, we have a carbon from a starting double bond. So here the second oxygen on Glycerol here is going to have four carbons. We have four carbons and we're going to have two car bles, one from the ether and the other on the third position from our starting double bond. And I'm going to go ahead and scroll up once more just to check that. All right. So now we can focus on our final fragments here. If I consider fragment four, the longest carbon chain is comprised of five carbons. However, carbons, one and four were part of two starting double bonds, meaning that both of those positions in fragment four should contain Caron. So it's five carbons, one car bal on position one and another on position for and last but not least, we have the fifth and final fragment, which is composed of only three carbons, the first of which was part of the double wand. And so that one is getting a car B and there you have it. So here is our final answer, right? All five of these fragments would be the products of the given Ozono assis reaction. So if you stuck around until the end of this video, I appreciate you watching. Thank you very much and I hope we found this helpful.

Predict the product of ozonolysis of the triglyceride shown.

Key Concepts

Ozonolysis

Triglyceride Structure

Fatty Acid Unsaturation

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