Structural (constitutional) isomers (video)

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Structural (constitutional) isomers

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How to draw structural isomers using bond-line structures.

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• Is there a way to figure out by looking at the formula how many isomers there are without trying to draw them all out?•(19 votes)
  • Formula for number of isomers for a compund = 2^n, where n = number of chiral carbons in said compound.(8 votes)
• Is there no hydrogen bonded to the oxygen in the last isomer? Why?•(8 votes)
  • Because Oxygen only wants two bonds, and it already has those two bonds with the two Carbons it is connected to. There is no need for it to be connected to a Hydrogen as well.(12 votes)
• Is it possible to know how many isomers can be made from the molecular formula?•(5 votes)
  • There is a complicated computer program, but the easiest way is by systematic trial and error.(7 votes)
• the compound C3H8O is Propanol right?•(3 votes)
  • There are 3 different molecules (isomers) that have that formula (C3H8O).
    Jay draws all of them in this video.
    They are: propan-2-ol, propan-1-ol, methoxyethane(8 votes)
• Pentane with molecular formula C5H12, exists in three isomeric forms. One shows linear carbon chains, another has one -CH3 groups present on the third carbon atom, and the third has two -CH3 groups present on the second carbon atom. What types of isomers are these? geometric,structural,or halotropic? plz help me•(2 votes)
  • Structural isomers have the same formula, but the atoms are bonded together in different orders.
    That agrees with the description in the question.
    These are all structural isomers.(5 votes)
• where can i find questions to practice ?•(4 votes)
• Athow do we know that Oxygen has two lone pairs? I understand that it wants an octet, but how do we inherently know it is not there without fulfilling the octet rule?5:43•(1 vote)
  • O is not one of the atoms that violates the octet rule.
    In a stable compound, it will have 8 valence electrons.
    In this compound, it has 2 bonding pairs (4 electrons). There must be 4 unshown electrons, so they will be present as 2 lone pairs.(4 votes)
• I’m still trying to figure out how CO, carbon monoxide works. How does oxygen get a triple bond with carbon? Is this an example of an SP bond? I thought oxygen only had 2 covalent bonds available.•(1 vote)
  • Something to keep in mind, carbon will almost always follow the octet rule. CO isn’t an exception to this. The third bond here comes from a lone pair on O being shared with C. Yes the hybridisation is sp for both O and C.
    Experimentally we find the bond length in CO is shorter than a C-O double bond and similar to the N-N triple bond length in N2. So a triple bond in CO here does sense.(2 votes)
• At, why is that structure of C5H12 not a structural isomer but the structure at3:00is? Isn’t the OH being placed at the 1st carbon and not the 2nd the same idea as the C being placed at the 3rd carbon and not the 2nd?6:55•(1 vote)
  • Atit is exactly the same as the structure above it just rotated around.3:00
    Atnote the length of the carbon chain is 3. The OH can be on either the end carbon or the middle carbon and these give different structures.6:55
    So no it is not the same thing at all. If he used a 4 carbon chain for the second example and tried to put the OH on the 2nd carbon of one structure and the 3rd carbon of another, it would result in the same structure too.(3 votes)
• In the second example, can’t we have a ring of 3 carbons and attach an OH to one of the three carbons in the ring?
  Thank you.•(1 vote)
  • So the molecule you’re describing is known as cyclopropanol. However cyclopropanol has a molecular formula of C3H6O, which is of course different from C3H8O and would not be considered an isomer to the other molecules because of the different number of hydrogen atoms.
    Hope that helps.(2 votes)

Video transcript

– [Voiceover] Let’s say we’re asked to draw all the structural isomers that have the molecular formula C5H12. The word “isomer” means same parts. And so we’re talking about the same number of atoms. All of our structural isomers are gonna have five carbons and 12 hydrogens. Our isomers are gonna differ in how those atoms are connected to each other. So they differ in terms of their structure. And that’s why we call them structural isomers. We can also call them constitutional isomers. So we need five carbons. So for our first isomer we could just draw five carbons in a chain. So here are my five carbons in a chain. And you should have already seen the video on bond line structures before you watch this one. So let’s draw those five carbons and let’s double check and make sure we have the correct number of hydrogens. The carbon on the far left has three hydrogens, so here we have our three hydrogens. Next carbon has two, same with the next carbons, so two for this one, two for the next carbon, and finally three hydrogens for the last carbon. So let’s count up everything and make sure we have to correct molecular formulas. We have one, two, three, four, five carbons. So that’s C5. And then we should have 12 hydrogens. Here’s three plus two gives us five, plus two gives us seven, plus two gives us nine, and then we have three more for a total of 12. So, C5H12 is the molecular formula for this compound. Let’s draw another structural isomer that has the same molecular formula. So instead of drawing five carbons in a chain now we have to draw four. So let’s start by drawing four carbons. We need a total of five carbons so we need to show the fifth carbon branching off of our chain. So we could show the fifth carbon branching off of our chain here. Let’s draw in those five carbons. So here we have our five carbons. Let’s count up hydrogens. Carbon on the left has three, so three hydrogens here. Three hydrogens on this top carbon. There’s only one hydrogen on this carbon, two hydrogens on this one, and finally three hydrogens on this carbon. So let’s count up our atoms. So let’s use red for this one. We have one, two, three four, five carbons. So that’s C5. And then for hydrogens we have three here plus three gives us six, plus one gives us seven, plus two gives us nine. And three more for a total of 12. So C5H12 is the molecular formula for this compound. So these two drawings represent two different molecules. Both these molecules have the molecular formula C5H12. But they differ in terms of how those atoms are connected. They differ in terms of their structure. So we call them structural isomers of each other. All right, to draw another structural isomer, some students might say, “We could start with “four carbons in our chain again.” And this time, instead of showing a branch off of this carbon, we could show a branch off of this carbon. And so a student might draw this structure and say, “Okay, there’s a different structural isomer.” But actually these are just two different ways to represent the same molecule. If you analyze that second structure that we just drew the connections are the same. We have a CH right here bonded to a CH3, bonded to a CH3, and bonded to a CH2. And the CH2 is bonded to a CH3. That’s the same structure as what we drew out over here. So it looks like it’s a different structure. It’s a different drawing than the one up here, but actually this is just two different ways to represent the same molecule. So we have two structural isomers so far. Let’s think about one more. So we can no longer do four carbons in our chain so we go down to three carbons. So we start with three carbons in our chain. We know we need a total of five carbons. So we need to show two more carbons added to our chain. And these would have to add those two carbons to our central carbon like that. Let’s draw out all of our carbons here. And let’s add in our hydrogen. So this carbon would have three hydrogens same with this carbon. And the same with this one, and finally the same for this carbon. The carbon in the center, this carbon in the center here, already has four bonds. So it doesn’t have any hydrogens on it. Let’s count up everything. Let’s count our carbons first, one, two, three, four, five carbons, so C5. And then we have three hydrogens plus three is six plus three is nine plus three is 12. So C5H12 is the molecular formula for this compound. And this is another structural isomer. So it’s a different molecule from the other two. So we have a total of three structural isomers that have the molecular formula C5H12. Now let’s draw all of the structural isomers that have the molecular formula C3H8O. And we’ll start with the molecule we talked about in the bond line structure video, so that molecule look like this. We have three carbons and then we have an OH coming off of the central carbon. Let’s expand that out and make sure that this has the correct molecular formula. We have our three carbons. And on the middle carbon we have an OH. So an oxygen bonded to a hydrogen. I’ll go ahead and put lone pairs of electrons on this oxygen. How many hydrogens do we need to add to the carbon on the left? Well, we need to add three hydrogen. So we go ahead and draw in those three hydrogens. The carbon in the center already has three bonds so it needs one more so we add one hydrogen to that carbon. And the carbon on the right needs three hydrogens. So let’s count everything up now. So we’ll start with our carbons. We have one, two, three carbons. So that’s C3. We have three hydrogens here and three here, so that’s six plus one is seven, and don’t forget about the hydrogen on the oxygen for eight. So we have eight hydrogens. And obviously we have one oxygen here. So I went ahead and put in lone pairs of electrons on that oxygen. So the molecular formula for this molecule is C3H8O. And if I number this, if I said this was carbon 1 and this was carbon 2, and this was carbon 3, that helps us to draw the next structural isomer because we could think about instead of that OH group coming off of carbon 2, what if that OH group came off of carbon 1? And so let’s draw out our three carbons here. And now we put our OH group coming off of carbon 1. And let’s expand this out and draw the Lewis dot structure and make sure that this has the correct molecular formula. So we have three carbons, again, in a row. And then the carbon on the left is bonded to the oxygen. The oxygen is bonded to a hydrogen. I’ll put in lone pairs of electrons on the oxygen. Now we need to add in carbon hydrogen bonds. So this carbon needs two. The next carbon also needs two. And the carbon on the end would need three. So that’s one, two, and three. When we add everything up let’s use blue for that, that’s one, two, three carbons. We have C3. We have three hydrogens here, plus two is five, plus two is seven, and one here is eight. So C3H8. And then, of course, our oxygen. So C3H8O is the molecular formula. Next. Some students might think, “Okay, well, “we put an OH coming off of carbon 1 “but what if I put an OH on the other side?” So, over here on the other side. So let’s see what would that give us. If I put an OH coming off of that carbon, hopefully it’s obvious that these two represent the same molecule. There’s no difference in terms of how those two are connected structurally. So this is the same molecule, so two different ways to draw the same one. So this is not a new structural isomer. Just a new way of looking at this molecule. Now let’s draw one more. So we can’t put the OH on the other carbon. So now we have to figure out something else that we can do. Well, we could, this time, put two carbons in a row and put an oxygen in between, so putting an oxygen to break up our carbon chain. So now this would be carbon bonded to carbon bonded to oxygen, bonded to carbon. And then we fill in our hydrogen, so there would be three on this carbon. There would be two on this carbon. There would be three on this carbon. And I could put in lone pairs of electrons on the oxygen like that, and can everything up. So we have one, two, three carbons, so that’s C3. We have three hydrogens plus two is five, plus three is eight. So we have the H8. And then, of course, the one oxygen. So this is another structural isomer. Again, some students might say, “Well, we could go like this,” and this would be yet another structural isomer like that. But really this is just another way to draw this molecule. So it’s not a new structural isomer. It has the same connections. So we have a total of three structural isomers that have the molecular formula C3H8O. And as you go further in organic chemistry you’ll learn that the first two isomers we talked about, so this one and this one, the ones that have an OH on it, those are called alcohols. And the last structural isomer is called an ether. So we’ll worry about that more later in other videos.