Concept: Concept: Carboxylic Acids Nomenclature5m
Before we can learn to react with carboxylic acids, we need to know how to name them. Let's talk about carboxylic acid nomenclature. There's two really competing and popular ways to name carboxylic acids and I’m going to teach you both. There's the IUPAC system and the common name system, and they're both good in their own ways. You're going to see them both this semester. Let’s start off with the easier one, IUPAC. In the IUPAC system, carboxylic acid is going to be a modifier. You’re going to modify your root chain. You take out the e and your place the e with the suffix -oic acid. This should make sense. If you think about it, you've heard of benzoic acid before. That's that ending there. Substituents are located using numbers. Same thing we're used to. If you have a two methyl group, you would put 2-methyl. Everything is normal. The common name system is a little bit tricky because it turns out that carboxylic acids are some of the oldest compounds to be studied so they were given means far before the IUPAC convention of 1919. What that means is that sometimes you're going to see carboxylic acids named with the common naming system. Let me give you case in point. How often have you heard of ethanoic acid? Probably not that often. How often have you heard of acetic acid? You’ve heard about that since general chemistry. Why do we call it acetic acid? Where does that name come from? It doesn't come from IUPAC. That’s a common name. Like acetic acid, we're going to need to learn these common names.
The way that we name carboxylic acids with common means is by memorizing the first five common names. Their common names have to do with how many carbons are in the chain. A one-carbon carboxylic acid is formic acid. A two-carbon is acetic acid. Three carbons is propionic acid. Four is butyric acid. Five is valeric acid. I'm not going to ask you to go more than five. Your professor probably won’t either but then again, it's between you and your professor. I really haven't seen anything more than five in introductory Orgo 1 and 2. That means that in general, whatever alkane you have, if you’re naming it in IUPAC way, it becomes alkanoic acid. That’s what we’re naming. The exact name depends on the identity of the alkane.
Also, something I’m jumping around, but I told you that you have to memorize these common names but it turns out that there's another difference. When you're using common names, you don’t locate substituents with numbers. I know. It doesn't make sense. But instead you’re going to use the Greeks. You’re going to use the Greek symbols. When I mention Greeks, I'm talking about alpha, beta, gamma, delta, epsilon. Again, first five. I don't think you should have to know beyond epsilon. If you're pledging in a sorority or fraternity, you should probably know beyond epsilon but for right now, that's going to work. We’ve got these two different systems. You need to know both.
Finally, one last thing and then we’ll start some practice problems. Whenever you have a negative anion of a carboxylic acid because you know that these things tend to give way to protons. Oftentimes, you'll see a carboxylic acid as an O negative. If you see it as an O own negative, you’re going to replace the oic acid, you’re going to replace that with -ate. Ate being the suffix for a negatively charged species. Acetic acid turns into acetate when it's a negatively charged species. That should just make sense. What I want you guys to do is look at this first compound, give me both the IUPAC name and the common name as best as you can do and then I’ll step in and help you guys out.
Concept: Example: Give the IUPAC name3m
Concept: Concept: Diacids2m
Problem: Provide the common name for the following compound.4m
What is the IUPAC name for the following compound?
A) 1,3-ketobutanoic acid
B) 1,3-oxobutanoic acid
C) 1-oxobutan-3-oic acid
D) 3-oxobutanoic acid
E) methyl butaoxoketone
Give the IUPAC name for the following structure.
In the space, draw the following molecule: (3S,6R)-3,6-dihydroxyoctanoic acid
Draw the correct structure for the compound below.
Draw the structure for (2R,4S,5E,8S)-4-amino-8-chloro-2-hydroxy-7,9-dioxonon-5-enoic acid