Using curved arrows, show the mechanism of the following react...

Question

Using curved arrows, show the mechanism of the following reaction:

Curved arrows illustrate the reaction mechanism involving acids and bases, showing electron movement between molecules.

Accepted Answer

Everyone. And welcome back, show the mechanism of the following reaction. Using curved arrows, curved arrows allow us to understand how reactions take place in organic chemistry. And mechanisms allow us to visualize all of the process. The main concepts we want to remember are electro files and nuclear files. Nuys are electron rich species which are electron pair donors. Whenever we are creating new bonds, electro files, in contrast, our electron poor species which are lone pair acceptor. Recall that whenever we are using mechanisms, our arrows will start from nuclear files and we will go towards electro files showing the new bond formation. Looking at the two structures at the very beginning, we have one of them being positively charged. So it must be our electro file. The other one has oxygen with lone pairs. So it's electron which it must be our nuclear file. It's also not charged, which supports that statement. We noticed that the product formed looks similarly. It's the first structure which is our new file. But now we have hydrogen bonded to oxygen. And the reason why that happens is that because our nuclear file oxygen from the carbonyl group uses its loan pair to accept the proton from hydro num. And if we are accepting that protein, we are creating that. 01 notice how oxygen only has one lone pair remaining because the other one has been used from the nuclear file to create that oh bond. And therefore, if we are accepting that proton only, we have to remove water as a byproduct. Right. So we have to break that oh bond and do that because electro files do not give us any electrons. We are going to use both of these oxygen hydrogen electrons and transfer them onto oxygen in a form of a lone pair. That's how we get water with two long pas and oxygen, right? So we got our first two arrows, the nucleate hydrogen followed by the loss of water. Hyen doesn't contribute to any electrons, right? Because the two hydrogen oxygen electrons within the val bond have been used in the formation of a lone pair and oxygen well done. So we got our proton structure and it says that it's treated with water and we are forming a specific intermediate. And if you look carefully at it, you still have your c three group, you have hydrogen on the right above your carbon. You have oh But you have broken the pie and you have an extra pair in oxygen. And that makes sense, right? Because that lone pair comes from the pi bo. So the pipe has been broken, we have transferred our p electrons in the form of a lone pair on oxygen. In addition to that, you may notice that we have created our carbon oxygen bond from water because we have ohh. And that means h2o. So we are simply taking our nuclear file. In this case, our nuclear file would be water because it has too long pairs on oxygen. Our electro file will be the proton form of the aldehyde, right? Because it has a positive charge. So we understand that the electron flow will start at the nu coile at the long pair of oxygen and it will attack our carbon group and specifically the carbon atom within the carbon because you notice that you're forming carbon oxygen bond. But at the same time, you have to break another bond if you're breaking a new one at that carbon. So that's how we broke our pipe bond and got that extra lone para andox. So that makes sense. Those are the two arrows. Now, we got formal positive charge on oxygen because that oxygen contains three bonds, two original hydrogens and oxygen carbon bond. Also, you may notice that there's only one loan pair remaining because one of them has been used in the formation of that bond. So everything is consistent, well done. And then the final step, if you look carefully, the structure that we get looks very similarly, but we are removing that proton and for that purpose, water is used. So once again, the electro file is the one that contains a positive charge. The nuclear file mu mu must either have a negative charge or alone pairs. So that means water must be our nuclear file since it has some pairs and it's not possibly charged. So from here, we are using the pair of oxygen and water, we're capturing that protein. And the reason why we're doing so is because we're forming hydro num, you may notice how there's only one lone pair instead of two. So that lone pair from auction has been used in the formation of oxygen, hydrogen bond. And because we are only capturing that proton, we must transfer hyen oxygen electrons onto oxygen in the form of a alone pair. And that's why we got two loan pairs in auction. So that's also consistent. That would be it. We got, we got all of our curved arrows and we have showed the complete mechanism based on what we see here. We may conclude that the correct answer to the multiple choice question is C thank you for watching.

Using curved arrows, show the mechanism of the following reaction:

Key Concepts

Curved Arrows in Mechanisms

Acid-Base Reactions

Resonance Structures

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