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Organic chemistry naming examples 4

Organic chemistry naming examples 4. Created by Sal Khan.

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  • blobby green style avatar for user Niall Joyce
    When 'Tetra' means theres 4 methly groups, whats the other names for the other numbers of groups - 1,2,3,5,6,7 ?? thanks
    (6 votes)
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    • purple pi purple style avatar for user Luke
      Matthew's answer is not totally accurate. The di/tri/tetra prefix doesn't need to refer to substituents on the same carbon. For example, 2,2,6,6,7-pentamethyloctane (from one of Jay's videos) would be the correct IUPAC name, even though there are 5 methyl groups.

      So, to answer the question:
      5 - penta
      6- hexa
      7 - hepta
      8 - octa
      9 - nona
      (20 votes)
  • spunky sam blue style avatar for user Abol3ela
    I still can't get the iso sec tert prefixes ? How can I differentiate between them
    (5 votes)
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  • blobby green style avatar for user laurensaggio
    > when numbering the carbon chain of the substituent (in doing the SYSTEMATIC approach, not common name approach), is it a general rule to number carbon '1' as being the carbon connected to the parent group?

    In completing the 'answer' before seeing Sal do it, I had trouble knowing which carbon was carbon '1', on the methylethyl substituent, and thus didn't know where to put the two methyl groups.

    thanks! lauren :)
    (8 votes)
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  • starky ultimate style avatar for user ST
    Who came up with the systematic way of naming?
    (4 votes)
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    • piceratops ultimate style avatar for user inverse of infinity
      it was IUPAC.It made a group known as IUPAC nomnclature in those days and told everyone to bring there names for the compounds and the reason behind naming them like that.Many people came up but one of them(i don't remember the name)came up with what is the base of organic chemistry today
      hope that helps.
      (7 votes)
  • blobby green style avatar for user Dorien Baudewyns
    why is your cyclohexadecane not a beautiful ring-form? you just made a kind of double ring in one?! you did this just to have a bit of structure maybe?!
    (0 votes)
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    • leaf green style avatar for user brianmantz2
      At this point in the series, it is not possible to know that we are talking about lawn chairs. I think the reason it is drawn like this is when you draw a ring of 16 segments it really starts to look like a circle and so drawing it more wiggley helps in the counting.
      (7 votes)
  • starky ultimate style avatar for user Juan Ignacio Martony
    How do i know the shape of the cyclohexadecane? Do for example a regular and one like Sal drew behave chemically different?
    (4 votes)
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    • mr pants purple style avatar for user Ryan W
      As long as you join 16 carbons together in a ring it shouldn't really matter to your teacher. You couldn't know the shape beforehand really, and I don't think Sal has it quite right here anyway. But like I said, it shouldn't matter.
      (4 votes)
  • piceratops tree style avatar for user Maria Fernanda Garcia
    What is the difference between bis- and di-?
    (4 votes)
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  • blobby green style avatar for user zabih.khogyani
    What is BIS in the latest example? you are not referring to it at all.
    (2 votes)
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  • blobby green style avatar for user 173690
    At , when the connection to the middle carbon is made to the ring, does that count as another carbon connection? Or is that connection just there to form the Y shape? I'm confused... I see that the connection has to be made for the isopropyl group to be attached to the ring, however does it serve as another carbon attachment? Or is it just solely there to be used as a connection to the cyclohexadecane?
    (2 votes)
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    • orange juice squid orange style avatar for user Anubha18
      The connection is not another carbon but simply a connection to join it to cyclohexdecane. If we name them in the other way one purple line and one yellow line makes the ethyl and the other purple line being the methyl. Which in other words is isopropyl. Hope this answered your question. :)
      (1 vote)
  • starky ultimate style avatar for user ST
    Where can you get the official rules for systematic naming?
    (1 vote)
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Video transcript

We've done a bunch of examples looking at the actual molecular structure and trying to come up with the name. In this video, we'll go the other way around. We'll start with the name and see if we can actually draw the molecular structure of whatever this might be. So let's start. When you first look at these, it's very daunting, but you always want to start really at the end, so you know what kind of the core of the structure is going to be. So if you look at the end of this, you have an -ane, so there's not going to be any double or triple bonds here. It's all single bonds. It's a hexadecane, so let's think about that. Hexadec-, that's six and ten. Hexadec- was a prefix for 16, so this is 16 single-bonded carbons. And cyclohexadecane, so 16 single-bonded carbons in a ring, so this part of it right here. So let me just do this. So cyclohexadecane, let's draw that part first. It's not easy to draw even a 16-carbon ring, so let's start here. One, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, and then sixteen. I think I got it. Let me count them again and then I can connect them up into cycles. It's one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen. All right, I drew the cyclohexadecane part. Now, if we go back a little, let's see, we have a 2,9-diisopropyl. What does this mean? This means that we have an isopropyl at the two and the nine spot. Now when you are drawing the structure from the name, you could just arbitrarily on someplace on this ring pick what your one through your sixteen spots are. I'll just arbitrarily pick them, because I could have drawn this ring any which way. One, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen. All right, so this next piece right here, let me do this in magenta. 2,9-diisopropyl, this is telling us that at spot number two and at spot number nine, I have isopropyl. The di- is just saying I have two isopropyls at two and nine, so you can kind of ignore the di-. I have an isopropyl, and you may or may not remember that an isopropyl looks like this. It's three carbons, so it's going to be one, two, three, and the connection point to the main ring in this case is going to be in the middle carbon, so it kind of forms a Y. All of the isos, the isopropyl, isobutyl, they all look like Y's, so it's going to be linked right over here. That's also going to happen at the ninth carbon, so at the ninth carbon we're going to have another isopropyl. We're going to have another isopropyl at the ninth carbon. All right, we've taken care of the 2,9-isopropyl. Then we have the 6-ethyl, which is just a two carbon. Remember, meth- is one, eth- is two, prop- is three. Let me write this down. So this is going to be prop- is equal to three. Isoprop- is equal to that type of shape right over there. In this case, eth- is equal to two, so it's a 6-ethyl group. So at six we have an ethyl group, so one, two, carbons, and it's connected at the six carbon on the main ring. And then finally we have a cyclopentyl. So if we look at-- let me find a color I haven't used yet-- cyclopentyl. so pent- is five, but it's five in a cycle, so this is a five-carbon ring that's branching off of the main ring. It's at the first spot. Let me draw a five-carbon rings, so pent- is equal to five, so it would look like this, one: two, three, four, five. It looks just like a pentagon. That's a cyclopentyl group and it's attached to the one carbon on my cyclohexadecane, so it is attached just like that. We're done. We've drawn 1-cyclopentyl-6- ethyl-2,9-diisop ropylcyclohexadecane. Let's do another one. I think we're getting the hang of it. So here, maybe we can do this one a little bit faster. Let's see, we have a tetramethyldodecane, so the main root here is the dodecane, do- for two, dec- for ten. This is a 12-carbon chain. It's not in a cycle, so let me just draw it out. We have one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, and so we can just number them arbitrarily, just because I could have drawn this any which way. So it's one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve. That's the dodecane, all single bonds. Then we have a 3,6,9,9-tetramethyl. All this is telling us-- remember, meth- is one carbon, so all this is telling us is at the three, the six, the nine, so at the three, the six and twice at the nine spot, we have methyl groups, and we have four methyl groups. That's all the tetramethyl is saying so it's a little bit redundant. We know we have four of them here: 3,6,9,9. We have methyl groups at each of those places. We have one methyl group at three, and then that is bonded with the third carbon on the dodecane chain. We have one at six bonded to the six carbon on the dodecane chain. We have two at nine, so that's one at nine and then we have another one at nine bonded to the nine carbon on the dodecane chain. And we're done. That's it. That's 3,6,9,9- tetramethyldodecane. Let's do another one. 1,3-bis(1,1-dime thylethyl)cyclopentane. So once again, just kind of breathe slowly. It's very daunting right when you look at it, but just start with the core: cyclopentane. That's just a simple five-carbon ring. A five carbon ring that looks like a pentagon: one, two, three, four, five. There you go. That is a five-carbon ring. We can number it however we want, so one, two, three, four, and five. This is telling us at the one and the three position we have-- and the bis- is kind of redundant. This is saying we have two of these things. Obviously, we have two. We have one at the one and one at the three. So you can kind of ignore the bis-. That's just the convention and we've seen that multiple times. But at each of those positions, we have a 1,1-dimethylethyl. So what's a dimethylethyl look like? So let's think about it a little bit. Let's think about it and let me do it orange. They obviously named it using systematic naming and what we have here, we have an ethyl as kind of the core of this side chain. So if an ethyl is equal to two carbons, so this is two carbons right there. So let me draw a two carbon: one, two. That is two carbons right over there. I'm just drawing it at the three spot. I'll draw it also at the one spot, actually. So that is two carbons right there. That's the ethyl part. And then on 1,1, so if we number them, we number where it's connected, so it's one, two. This is saying 1,1-dimethyl. So on this ethyl chain, you have two methyls. Remember, methyl is equal to one, so this is one carbon. You have one carbon. That's what methyl is, but you have two of them. You have dimethyl. You have it twice at the one spot. So you have one methyl here and then you have another methyl there. Same thing over here. You have 1-methyl on the one spot and then you have another 1-methyl on the one spot. And then you are connected at positions one and positions three, so you're connected there and you are connected right over there. And you're done, That's it. That is our structure. Now, if you did this with common naming, instead of this group being a 1,1-dimethylethyl, you might see that we're connected to a group that has one, two, three, four carbons in it. The carbon that we're connected to branches off to three other carbons. It is a tert-butyl. So you can also call this a 1,3-- let me just write it down. So another name for this would be 1,3-tert-- or sometimes people just write a t there-- t-butylcyclo-- no, actually I should say di-t-butyl, because we have two of them. 1,3-di-t-butylcyclopentane.