1) NaNH 2 2) CH 3 Br 3) H 2 /Lindlar's catalyst

All right, guys. So in terms of alkenide retrosynthesis, it really isn't going to get easier than this. My first step was that we needed to make this a nucleophile. Right now, triple bond is not a nucleophile unless it gets deprotonated. So my first step, what I want to use is just some kind of strong base like NaNH2. Okay? What that's going to do in my first step is it's going to deprotonate my alkyne to turn into an alkynine. Okay? Because there's an H here that gets deprotonated by the NH two negative that pulls it off. Now I've got that triple bond. Now you guys should know what do I react that triple bond with or that alkynide with to add one more carbon. I should react it with an alkyl halide that has one carbon on it because alkyl halides are the electrophiles. So I should react it with CH3X. You pick the halogen. In this case, I'm going to pick br. But you could have picked I, you could have picked cl. F not so much. F isn't as good of a leaving group. So now I'm going to go ahead and write this here. Let me even draw it out a little bit better so you could see. This is going to be a backside attack. According to my flowchart, negatively charged nucleophile, methyl alkyl halide. That's a methyl. So this is going to do SN2 for sure. So I would get my back side attack. And what I wind up getting at the end of this is a triple bond that looks like this. Cool. Right? So now I have the right number of carbons. Notice that now I have 4 plus, of course, I have br negative. Who cares about that? That's just going to be a leaving group. So now it turns out that I can go from this to this in one step. What reagent is that going to be? So I told you guys we need to know how to make the alkanides, which we did. We made the negative charge. We need to know how to react it, which we just did. And we need to know how to transform it afterwards. The way we transform it is through hydrogenation reactions. So in this case, we would hydrogenate it with H2 over Lindlar's. Why? Because this is a cis double bond. Make sense? And that's it. That's our end product. So see that wasn't so bad, but you just have to get used to this idea of working kind of working backwards and thinking what do I need to do to make it look more like that. Okay? So does that make sense so far? Now go ahead and try to do this next one. What you're going to notice about this next one is that it's already getting worse because in the first one, I was easy on you guys. I just gave you a triple bond right there. Now, I'm giving you a double bond. Double bonds don't react the same way as triple bonds. So you're going to need to figure out what to do with that in order to make it look like this. All right? So go ahead and try your hardest to get this one right.