Propose a structure for the following compound, C 5 H 10 O with the given 13 C NMR spectral data: Fully Broadband decoupled 13 C NMR and DEPT:206.0 δ (↑); 55.0 δ (↑); 21.0 δ (↓)& 11.0 δ (↑).

Hey guys, let's take a look at the following practice question. Here it says propose a structure for the following compound, C5H10O with the given carbon 13 NMR spectral data. Here I give us the fully, broadband decoupled carbon 13 NMR as well as depth information. Remember, fully decoupled broadband just means that all the carbons appear as synclides, which really is useless. Depth helps us to identify if we have any CH, CH2 or CH3 groups. The problem here is I don't tell us depth 90 or depth 135, so I made this question a little bit more challenging. But here, we can make some assumptions. First of all, we have a signal around 206. Remember, if your signal is above 150, then it could only represent a carbonyl. Now, here it has a positive peak which means it could be either a CH or a CH3. Now, it can't be a CH3 because that carbon can't have 3 hydrogens on it because if it did, it would be making 5 bonds. Carbon at the most can only make 4 bonds. So that must mean it's a CH group, which means we have an aldehyde, which is always terminal. It's always at the end. So we figured out a portion of our molecule. Let's look at the other things. What else do we have? We have here a positive peak, which again can mean CH or CH3. This negative peak here, this downward arrow, means it could only be a CH2. We know we have a CH2 for sure. And then here, this is a CH or CH3. We know we have at least a CH2. What we could try to do here is plug it in, CH2. Now, let's make some other assumptions here. So far, how much of our formula have we used? Our formula is C5H10O. We've used 2 carbons and we've used 3 hydrogens and the oxygen, leaving us with C3H7O. Now, here, if we made one of these a CH, one of them a CH3, so if we have one of each, then we'd be using 2 carbons and 4 hydrogens, which will leave us left with what? A CH3. Which means what? Which means we must have 1 CH and 2 CH3s. So here we just have to draw this. We're going to say here we have a CH connected to 2 CH3s. This here would be our unknown compound. Again, carbon 13 NMR structural determination is much more difficult. Not very much information is given. Usually, you wouldn't get a question like this as a stand alone question. We would combine it with proton NMR or IR as well in order to give you as much information as possible that you have the best way of getting to the correct answer. This one, I just wanted to see if you guys could form connections and see how exactly could this molecule combine together from that unknown molecular formula.