Organic Chemistry

Learn the toughest concepts covered in Organic Chemistry with step-by-step video tutorials and practice problems by world-class tutors.

21. Enolate Chemistry:Reactions at the Alpha-Carbon

Malonic Ester Synthesis

1

concept

General Reactions

clock
1m
Play a video:
Was this helpful?
Alright, guys. And we're going to take a look at the other form of beta die carbon you'll Esther Reactions, which is melodic Esther synthesis. So, guys, you see this chart and you're thinking, Oh, my gosh, Another set of regions that I need to memorize. You're probably getting depressed, but don't. This is the same exact thing. Is aceto acidic? Esther notice that every single re agent here hasn't changed. Nothing has changed. The Onley difference is that because I'm starting off with melodic Esther, I have an extra ET group over here. What that means is that after I hide relies, not just this one turns into carb oxalic acid. They both do. So that means that the only difference between Aceto aesthetic Esther and melodic Esther synthesis is that my products have carb oxalic acids at the end. That's it. Everything else stays the same. So you could literally take everything you learned from aceto acidic acid. And when you see Milan IQ, just draw the same thing as his seed ascetic acid and add the car oxalic acid at the end. All right, so I'm not even going to go over every reaction here because this is the same as Milan ic acid. Er, melodic guest. I mean ah, seat of a city jester. So let's go through this practice problem. Go ahead and try to solve it yourself, and then I'll stop it step in and help.
2

example

Predict the Products

clock
4m
Play a video:
Was this helpful?
Hey, guys. So one word of caution here, if you feel like you couldn't get this question right, because you're having a hard time interpreting this content structure, you probably need to go back and review condemned structures just saying, because we're pretty late in or go to and they could show up anywhere condense structures. I do have videos about them. Okay, so if you need extra help, I got you. But anyway, the way you interpret this was it's a carbon with these two. Esther's coming off of it. So it b c o a t So that would be like that. And like that. And then, obviously it's c h two. So I'm just gonna put ahh cool. So again, this is just This is just another way to write Melania Esther. Okay, so the first step waas my base. Do you think that this base was a good choice for this Esther? Sure. Our group is the same. I don't have to worry about transits verification. The negative is gonna grab one of the h is and making easily. So I'm gonna make something. Looks like this. Okay. Now that easily is going to be exposed to the following alcohol. Hey, Lied something like this. So cl carbon carbon. Just make sure I'm getting this right. C h 32 Let's just make sure So ch 32 then ch ch two. Yep, that's right. Okay, so then we're gonna do a backside attack. What that's going to give us is now a melodic Esther. That is substituted. And what's attached now is I have my new bond. Well, I want to use a different color, have my new bond, and then I have the thing that attached so one to I believe that's right. Wait. Making sure I think I'm actually off. Yes, it should actually be. You see that? Is that And then that Is that Okay? Perfect. Okay, cool. Just making sure it's not a bad idea to slow it down and make sure that your county your carbons. Right. Cool. So there we have it. We just didn't calculation. The next step is what? Hydraulic assist. Now, guys, what's important about hydraulics is here is that you're gonna hide, relies both of your Esther's, right? So that means that you're going to get carb oxalic acid on one side and car works like acid on the other. You can't stop it plus your our group, Right then finally, we have D car box elation and guys, you're wondering, How do I know which one to D card box? Because we said that car oxalic acid Can the car Boxley? Well, it doesn't matter which one you could either take off the green one or you could take off the red one, but you can't take off both. So pick one. Make it go away. The other one stays. So let's just say the red one leaves That's going to give me Ah! Final compound that looks like this. Ohh Carbon. What's that Attached to carbon? Carbon? 123123 Something like that. Okay, plus my c +02 guys. Cool, right? So notice that once again, guys, I just did in Alfa Calculation. But I used melodic Esther to do it and noticed that I have a car box look acid as the end product because I started off with Melanie Melanie Tester. Alright, guys. So I hope that made sense. It's not as scary as it looks. It's actually really fun. There's actually one of my favorite reactions to teach. Most my students like it. Okay, so that being said, let's move on to the next videos
3
Problem

Provide the major product for the following reaction

4
Problem

Provide the major product for the following reaction

Divider