What's up, everybody? In this section, we're going to take a look at the full mechanism for the oxidative cleavage reaction, ozonolysis. The mechanism for the ozonolysis reaction proceeds through intermediates called ozonides. Alright. And what ozonides are, are there they are, cyclic molecules that were formed by the addition of ozone. Okay. So it was going to have 3 oxygens, and they're always going to be really unstable. Alright. That instability in these intermediates is what drives our reaction forward. Okay? And ozonolysis is always combined with a reductive or oxidative workup. Alright? The reductive workup forms aldehydes and ketones, while the oxidative state of the workup forms carboxylic acids and ketones. Okay? Our reagents for the reductive workup are typically either DMS, which is, dimethyl sulfide that we see right here, or zinc and acetic acid. Alright. For our oxidative workup, we typically use H2O2, which is just hydrogen peroxide. Okay? Now with this analysis, the mechanism proceeds the same through the first 3 steps regardless of which workup we're going to use. Okay. So we're going to break this up and first look at the first three steps that are common to either oxidative or reductive analysis. And then we'll look at the reductive workup mechanism and then the oxidative workup mechanism after that. Okay? So the general mechanism is 3 steps and each step has 3 arrows. Okay? So all this analysis mechanism has 3 steps and 3 arrows per step. Okay? In our first step, we react our alkene with our ozone molecule. Alright. What is our ozone molecule missing here? Yeah. It's missing its charges. Okay? Remember, we have a positive charge on this middle oxygen and a negative charge on that oxygen there. Okay? That negative charge is going to act as a nucleophile, and it's going to add to our double bond. Okay? So this negative charge is going to come in and add to our alkene there. Alright. We made a bond, so we have to break a bond. So we break the pi bond in that alkene and attack our oxygen at the far end of the ozone molecule. Okay? That breaks the oxygen-oxygen pi bond and puts a lone pair on oxygen. Okay. So we had our 3 arrows there. They're all moving in the same direction. That gets us to our first ozonide intermediate. Alright? And this intermediate is called molozonide. Alright. Remember, our ozonide intermediates are unstable. Alright. And that instability is going to drive this next step. Alright. But first, you may be wondering, where is this hydrogen right here? Where did that end up? Well, remember, this first step is going to be a syn addition. Alright. Where our ozone adds either from the top of that alkene or the bottom and the stereochemistry of that alkene is retained. So what I mean by that is that the hydrogen is cis to the ethyl right there. Okay. So it's going to be cis to the ethyl in our molozonide intermediate here. So that hydrogen is going to end up onto this wedge right there. Alright? So from here, this second step, it again has 3 arrows. Alright. We want to start at one of the oxygens that's making a bond to carbon. Alright. So either the one on the right or the left, and it doesn't matter here. Alright. So we can just choose one. We'll choose the one on the right here and we'll make a carbon-oxygen double bond. Alright. That's our first arrow. We made a bond. We have to break a bond and we're going to break the carbon-carbon bond that connects the two oxygens. Alright. So that is this bond right here in green. We're going to break that bond and we're going to make another carbon-oxygen double bond. Alright. Again, we made a bond, so we have to break another bond. So we're going to break this oxygen-oxygen bond and give that top oxygen a lone pair. Okay? So that gives us 2 molecules again. We have an aldehyde on the left. Alright? And then we have that other intermediate on the right. What are we missing on that molecule? You're missing our charges again. Okay. So we need a negative charge on that oxygen and a positive charge on this oxygen. Okay. And what we do next isn't actually a mechanistic step. It just makes it easier to draw the next mechanistic step. Okay. Okay. What we want to do is scoop up this molecule with the charges and flip it back towards ourselves. Okay? And when we do that, we end up putting that negative charge on the bottom here and the positive charge right next to it. Okay? The reason we do that is because these two molecules need to react together. Alright. And if you remember, the dipoles on carbonyls always look like this, where we have a dipole pulling electrons away from the carbonyl carbon towards that oxygen. Okay. So both of these carbonyl carbons have partial positive charges. So they're electrophilic. Alright. And then we have an oxygen with a negative charge. That's going to be nucleophilic. Okay. So we're going to do a nucleophilic addition here. And this step again has three arrows, and this negative charge will draw an arrow to the carbonyl carbon there. Alright. We made a bond. We have to break a bond. So we're going to break a carbon-oxygen pie bond, and that is going to attack the other carbonyl carbon. Alright. Our third and last arrow for this step is breaking the other carbon-oxygen pi bond
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- 1. A Review of General Chemistry5h 5m
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- 34. Nucleic Acids1h 32m
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10. Addition Reactions
Ozonolysis Full Mechanism
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