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Course: MCAT > Unit 10
Lesson 5: Stereochemistry- Stereochemistry questions
- Chiral drugs
- Structural (constitutional) isomers
- Chiral vs achiral
- Stereoisomers, enantiomers, and chirality centers
- Identifying chirality centers
- R,S system
- R,S system practice
- Optical activity
- Enantiomers and diastereomers
- Cis–trans isomerism
- E–Z system
- Conformations of ethane
- Conformational analysis of butane
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R,S system practice
How to assign a configuration to a chirality center using the R,S system.
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- In one of your videos before you teached an easier way to identify if its R ou S simply by ignoring the fact that the molecule with the lowest atomic number was not oriented back and then if you concluded that it was S it was because it would be R, why doesn't this work here?(24 votes)
- The lowest priority group is in the plane of the paper.
It is not in the front, so you can't use the easier way for a group in the front.(30 votes)
- Are the name of the molecules (R)-1-methyl-cyclohexene and (S)-3-bromo-3-chloro-pentane?(9 votes)
- The name of the first molecule is (R)-4-methylcyclohexene.
The double bond gets priority in the naming, and the numbers must include both alkene carbon atoms.
So C-1 is at the bottom, C-2 is at the 4-o'clock position, and the methyl group is on C-4.
The name of the second molecule is (S)-3-bromo-3-chloro-2-methylpentane.
You forgot the methyl group.(21 votes)
- At8:38, how is that molecule in the S formation? Since the chlorine is pointing away from us, why didn't we flip the molecule so that it would be in the R formation?(8 votes)
- but how do we vision holding the molecule and doing the rotation in a test where we only have pen and paper? is there any better way to help see it?(4 votes)
- Why wouldn't the second problem be R? I put S at first but then saw that the lowest priority was not going away in the figure the chlorine was so then I just chose the opposite configuration which was R.(4 votes)
- You have to view the molecule so the lowest priority group (ethyl) is going either directly away from you.
The ethyl group must be either a wedge or a dash. You can't leave it in the plane of the paper.(5 votes)
- How is this a chiral molecule? I thought that a carbon was a chiral center if it had 4 different groups attached.(2 votes)
- Every chiral carbon in this video has four different groups attached.(5 votes)
- So...if 1 is to the left of 2 - regardless of where 3 and 4 are - is it ever not counter-clockwise? It seems to me that the only information you need to determine R or S is 1's and 2's positions.(3 votes)
- Since we're always moving from group 1 to group 2, that initial direction always determines the configuration of the molecule. The third and fourth groups are good to label so that we know for sure we have the correct first and second group, but the rotation direction really depends on that initial group 1 to group 2 placement.
Hope that helps.(3 votes)
- Chiral carbon is one with 4 different atoms. In the first example, how is the carbon a chiral centre? It is attached to 1 x H-atom, 1 x CH3 and 2 x CH2.(3 votes)
- The chiral carbon does have a hydrogen and a methyl group, but the other groups aren’t simply -CH2 groups. This is because they are part of a ring system. For the chiral carbon to truly be chiral, the path around the ring would have to be different depending on the direction from chiral carbon. Going clockwise has alkene carbons, but going counterclockwise as only alkane carbons. These two different pathways mean those –CH2 groups are different, thus making the carbon chiral.
Hope that helps.(3 votes)
- how the 1st molecule has a chiral centre because the carbon is not attached to 4 different groups??(2 votes)
- Because that top carbon is bonded to an H, a CH3, and the left side of the ring isn’t the same as the right side of the ring due to the double bond.(4 votes)
- I am a bit confused..Actually if we rotate the molecule the Br will be on our left,the Cl on our right,no.3 pointing towards us and no. 4 pointing backward.And if we consider the numbering we will get it in a clockwise direction. Then it should be rectus right?(2 votes)
- I don’t see how you get clockwise there. If Br is on your left, Cl is on your right, and the iPr group is above and pointing towards you, then if you make a circle going from Br->Cl->iPr that is anticlockwise right?
He has a model of the molecule in the video, at7:50he puts it into this orientation.(3 votes)
- How do you differentiate which carbon within the double bond gains the additional carbon when deciphering R or S system? The location at 0.45 adds an extra carbon to the carbon on the right side of the double bond (to account for the double bond). Why does the extra carbon representing the double bond not get attached to the carbon on the left side of the double bond?(2 votes)
- You would do the same on the left side of it too. Both carbons of the double bond in this molecule would be considered as being bonded to 2 carbons and 1 hydrogen for the purposes of the R/S system.
But going down the right side of this molecule gets to the double bond first, so what you’re thinking about doesn’t matter in this case.(3 votes)
Video transcript
- [Instructor] Let's
get some more practice with the R, S system. So we'll start with this
compound right here. We already know from earlier
videos that this carbon is a chiral center. So let me go ahead and redraw everything because it's gonna help
us assign a configuration. So that's that carbon. We have a methyl group coming out at us. I'm gonna draw in the carbon
with the hydrogens here. We have a hydrogen going away from us. And going to the right around the ring, we hit a CH2, so I'm
gonna draw in a carbon with two hydrogens here. And then we hit a CH. So this carbon bonded to a hydrogen, that's this carbon on the ring. Notice that this carbon that I just marked is double bonded to this carbon. And for the purposes of R and S system, we're going to pretend
like this carbon is bonded to two different carbons,
even though it's really one. So that's how to handle a double bond. Going this way around
the ring, we hit a CH2, so I'm gonna draw that in. So here's our CH2. And then we hit another CH2 right here. So CH2. And then this carbon is
bonded to this carbon. So I'm just gonna draw a
line in there like that. All right, let's think about priority. So this is our chiral center,
let's look at the four groups attached to the chiral centers. So this is step one. Prioritize the four groups
using atomic number. So what's directly
attached to this carbon? There's a hydrogen, there's
a carbon, there's a carbon and there's a carbon. So carbon beats hydrogen
in terms of atomic number. So hydrogen is the lowest priority group. So we assign that a group number four. All right. Now we have a tie, we have three carbons. We have three carbons. So we need to see what those
carbons are directly bonded to. Let's start with this top carbon here. This carbon is bonded to
hydrogen, hydrogen, hydrogen. So let me write that down. So hydrogen, a hydrogen, a hydrogen. Let's move this carbon on the right. This one's bonded to carbon,
hydrogen and hydrogen. So carbon, hydrogen, hydrogen. We're thinking about the
atoms directly bonded to it, and we're going in
decreasing atomic number, which is why I put the carbon first. Now let's look at this carbon. So this carbon is bonded
to a carbon, a hydrogen and a hydrogen. So CHH. All right, let's compare now. Well, first point of difference. We look at the first atom
here, this is a hydrogen and this is a carbon. So carbon beats hydrogen. And then over here we have a carbon. So this one, this one doesn't win. This one must be third
in terms of priority. So I put a three here
for this methyl group. Now we continue on. We have hydrogen versus hydrogen. So that's a tie. Another hydrogen, another hydrogen. So we have another tie. So we need to go to the
next atom to break this tie. So we go to our next carbon. So this one right here. What atom is this carbon
directly bonded to? Well, it's bonded to
carbon, carbon, hydrogen. So carbon, carbon, hydrogen. This carbon is directly bonded to carbon, hydrogen, hydrogen. So carbon, hydrogen, hydrogen. We look for the first point of difference. This is a carbon versus a carbon. This is a carbon versus a hydrogen. So the carbon wins. And that means that this,
this way around the ring, this is the higher priority
path around the ring. So this gets a number
one, and then this path around the ring going this
way gets a number two. So now we've assigned a
priority to our four groups. So now we're ready for step two. Orient the groups so that
the lowest priority group is projecting away from us in space. So let's go back to our
original dot structure here. We said that this way around the ring was the highest priority. So this got a number one. Next, going this way around the ring was second highest
priority, so a number two. Our methyl group was a number
three, and our hydrogen was a number four. Our lowest priority group
is going away from us. Our hydrogen, our hydrogen is on a dash. So that's going away from us in space. So now we have, finally onto step three. And let me change colors again because it's getting a little busy here. So step three, determine if
the sequence one, two, three is clockwise or counterclockwise. So if I look one, two, three
and I go around the circle, here's one, here's two and here's three. So going around one, two,
three in a circle is this way, all right? That is clockwise, right? You can see that's clockwise right here. And so clockwise is R. So the configuration of
this chiral center is R. Now let's look at this compound. So we have only one chiral
center to worry about, it's this one right here. Let's think about the atoms
that are directly bonded to our chiral center. Well, there's a bromine
directly bonded to it, a chlorine, and over
here would be a carbon; and that we have another carbon. So we prioritize our groups
in terms of atomic number. Bromine has the highest atomic
number out of those atoms so we give bromine a number one. Next would be chlorine
with atomic number of 17. So that's number two. Then we have a tie for our carbons. So we need to see what is
directly bonded to those carbons. So for the carbon on the right here, this carbon is directly
bonded to a carbon here, a carbon here, and then
of course a hydrogen. So we write that in as
carbon, carbon, hydrogen. And then for the carbon on
the left, so this carbon, that carbon's bonded to a
carbon and two hydrogens. So we write in carbon, hydrogen, hydrogen. We look for the first point of difference. So we have carbon versus carbon. So that's a tie. So we keep going and we
get carbon versus hydrogen. So the carbon wins, and this group gets the higher priority. So this isopropyl group
is a higher priority than this ethyl group. So that means the isopropyl
group is gonna get a number three. So this is three. And the ethyl group is
the lowest priority. It gets a number four. Now that we've assigned
priority to our groups, we need to orient the molecules
so the lowest priority group is pointing away from us. And the lowest priority
group is group number four. So I'm going to a video in
a second, and in the video I'm gonna show you two
different ways to think about putting this group going
away from you in space. So one way would be to
just think about an axis through this carbon here and then rotate, and then rotate around
this axis until your lowest priority group is pointing away from you. Another way to think about it
is like a Newman projection. If you stare down, if
you stare down this bond, let me go ahead and change colors here, if you look down at this
carbon, carbon bond here, so if you put your eye along this axis, so here's your eye, that
would mean your lowest priority group, your ethyl group, would be going away from you. So that's another way to think about looking at the model or the molecule, I should
say, in a way where the lowest priority group points away from you. So here's our compound. Let's say that red represents bromine, so there's bromine; and
yellow represents chlorine. So our goal is to rotate
this to put our lowest priority group going away from us. So we think about an axis
through our chiral center, we'll rotate it so the ethyl
group is pointing away. And now we can see that our
red bromine is to the left, our yellow chlorine is to the right, and the isopropyl group is up in space. We go back to where we where. This time let's think
about a Newman projections. So we're staring down, staring down this carbon, carbon bond. So let's rotate the molecule. And it's a little bit
different perspective but we're still able to see
a red bromine to the left, a yellow chlorine to the right
and an isopropyl group up. So here's what we saw when we stared down our carbon, carbon bond. So this carbon is our chiral center. So that's this one right here. And then I used red for bromine and then I used yellow for chlorine. So we can see that our bromine, our bromine is to the left here, and this was the highest priority group. The chlorine is to the right. That was the second highest priority. And then we have our
isopropyl group here up. So that's one, two, three,
with our lowest priority group pointing away from us. So all we have to do now
is go around in a circle and see what we get. So we're going from one to
two to three in a circle. That means we're going
this way around our circle, and that of course is counterclockwise. So counterclockwise is S. So the configuration of
this chiral center is S.