Claisen-Schmidt Reaction

Concept: Concept: Claisen-Schmidt Reaction

Video Transcript

Now we're going to talk about a very specific type of crossed aldol reaction called the Claisen-Schmidt reaction.
The Claisen-Schmidt condensation is what happens when you have an enolizable aldehyde plus ketone. This means that we're kind of breaking the rules. Remember that I told you guys if you have a crossed aldol, then you should have one non-enolizable carbonyl. But this is the reaction that happens when you have specifically an enolizable aldehyde and an enolizable ketone both together. It turns out that you actually get kind of lucky if you mix an aldehyde and a ketone together that are enolizable because theoretically, they could both react and you would get a cross product. But what happens in real life is that one product does actually predominate. Why? Because it turns out that aldehydes are more susceptible to nucleophilic addition than ketones. It's going to favor one of the enolates over the other.
Basically, what I'm trying to say here is that you've got your ketone, let’s say and you’ve got your aldehyde. Theoretically both of these could form enolates. I could form an enolate, let’s say this is molecule A and this is molecule B. I could form an enolate on A. I could form an enolate on B and I would start getting a mess. I would get my Punnett Square. But what actually happens is that you only form the enolate on A. Why? Because B happens to be an aldehyde. It’s a group that is easier to do a nucleophilic addition with. Then it would prefer to be attacked and be the electrophile instead of being the enolate. With Claisen-Schmidt, it’s the one example where you actually can have enolizable cross reagents and you’re still just going to get one product. Makes sense?
You guys got this. Go ahead and predict the major product of the following Claisen-Schmidt condensation. Notice I have a ketone and an aldehyde. Notice they’re both enolizable. Try to predict it and then I’ll show you guys what the answer is.