Malonic Ester Synthesis

Concept: Concept: General Reactions

2m
Video Transcript

Now we’re going to take a look at the other form of beta-carbonyl ester reactions, which is malonic ester synthesis. If you see this chart and you’re thinking, “Oh my gosh, another set of reagents that I need to memorize.” You’re probably getting depressed, but don’t. This is the same exact thing as acetoacetic ester. Notice that every single reagent here hasn't changed. Nothing has changed. The only difference is that because I'm starting off with malonic ester, I have an extra OEt group over here.
What that means is that after I hydrolyze, not just this one turns into carboxylic acid. They both do. That means that the only difference between acetoacetic ester and malonic ester synthesis is that my products have carboxylic acids at the end. That’s it. Everything else stays the same. You could literally take everything you learned from acetoacetic acid, and when you see malonic, just draw the same thing as the acetoacetic acid and add the carboxylic acid at the end.
I’m not even going to go over every reaction here because this is the same as acetoacetic ester. Let's go through this practice problem. Go ahead and try to solve it yourself, and then I’ll step in and help. 

Problem: Provide the major product for the following reaction

7m

Problem: Provide the major product for the following reaction

4m

Concept: Practice 3: Malonic Ester Retrosynthesis

4m