Organic Chemistry

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14. Synthetic Techniques

Alkynide Alkylation

Organometals aren't the only way to create new carbon-carbon bonds. It turns out we can use a sodium alkynide (nucleophile) as well to react with alkyl halides and other electrophiles to form a new C-C bond as well. 



Sodium Alkynide Alkylation

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part of the synthetic cheat sheet taught you guys how to make new carbon carbon bonds. And that's what I want to focus on in this topic. I really just want to destroy the entire concept of organa medals and sodium Alka Night calculation. So, basically on you guys know this is the on leeway to make carbon carbon bonds and Orgel one is through or organo medals and strong sodium. Alka nights are really commonly used organa medals. And because they happen to be strong nuclear files, okay. And what that means is that since the strong nuclear falls, they're often paired or reacted with alcohol. Hey, lied because those air strong Electra files okay. And what we can do is we can get a negative on a carbon to be attracted to a positive on a carbon and ban. You have a new carbon carbon bonds, which is very important because synthesis relies on making bigger molecules from smaller ones. So if you can add carbons, that's really important. Okay, but for these, for sodium Alcon eyes were not just going to need to know that it's a nuclear thought and sex electoral. We're gonna need to know a few more things. How to generate the Alka Night. So that means like Alcon, I'd synthesis making it from scratch. We need to know how to do that. Also, after you've done your reaction, you also need to know how to transform the triple bond afterwards. So there's a lot to know here. We need to know how to make Falcon. I'd then how to use it and then how to lose it. How toe like, do different things to it. Okay, so once again, I had this graphic that showed different nuclear files. No one we're gonna be dealing with mostly on this page, because I want you guys to get special practice with. These are the Alcon nights and the occupy highlights. Okay, so we're going to do first is we're gonna start from this in kind of ascending hardness. We're gonna start with the easiest problem. It's not easy, but it's not that bad on. We're gonna work our way to progressively harder and harder problems where I'm gonna take you further and further back in the synthetic process, and you're gonna have to figure out everything from from the very beginning. Okay, but in this case like I'm telling you right now, this is not such a bad question. Let me coach you through it and see if you can get it. Because notice that right now. First of all, I'm already starting with the triple bond. That's awesome. Because if you're gonna notice, I have three carbons in this molecule. I have four carbons in the other. Okay, What does that mean? That must have happened at some point. Okay? If I added carbon, okay. If you added carbon, that means you must have used in organa metal. Okay, on. Like I said, the most common organo metal in this chapter is gonna be the sodium Alcon ID and already have a triple bond. So there's a huge give away that I just need Thio use that triple bond. Alright, So basically, what you should be thinking is how maney carbons do I need to add to the triple bond for to make four. And then what do I need to do to that triple bond after? So it looks like a It looks like a double bond. Looks like that. Okay, so that was enough hints. I'm just trying to coach you guys So this isn't totally like, you know, Total like a train wreck. And I'm gonna stop the video, and you guys try to answer it the best that you can.

Once we create these triple bond nucleophiles and use them in our synthesis, we will will also learn how to get rid of them and transform them to double bonds (cis and trans) and single bonds.


Let's get to work. These will be multi-step transformations. Do your best to see if you can fill in the correct reagents! 


Propose a synthesis:


Propose a synthesis: