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Organic chemistry
Introduction to chirality
Introduction to chirality (handedness), and how chirality is related to the groups bonded to a central carbon. Created by Sal Khan.
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- You take the mirror image of the left hand, and it looks like the right hand. As he demonstrated, you turn the left hand 180 degrees so that the thumb is on the left side. How does that not superimpose the right hand? On the right hand, the thumb is on the left side, and so is the left hand flipped 180 degrees? Same thing for the CFCH3Br molecule. If you flip the 180 CFCH3Br molecule 180 degrees, shouldn't the Br be in place of the CH3 in the original molecule, instead of the H? Thanks(48 votes)
- The hands are not superimposable. Imagine those two hands he drew have the palms facing away from you. If you were to rotate the left hand 180 degrees, yes it would have the same silhouette, but it would be palm up, whereas the right hand is still palm down. So no, they are not superimposable. A palm up left hand is not the same as a palm down right hand.(107 votes)
- At minute, Sal establishes that opposite hands are enantiomers of one another, but he says they are not "superimposable". Technically you can superimpose anything onto anything. I think the phase should be "not superposable", which means the hands do not coincide exactly when they are superimposed. 1:12(6 votes)
- I believe you have missed the point, or he didn't elaborate enough:
Non-superimposable merely means "not the same in 3D".
the point is not to just stack something on another. that is pointless
the idea is that you can not overlay your left hand on your hand (it's mirror image) with thumbs overlapping (superposing) thumbs and or pinkies with pinkies (and no you can't turn one hand upside-down and put them together like you're praying). The fact that right and left handed gloves exist proves this. They will never be the same in 3-D. That is what non-superimposable means. And that is why chirality matters. (Enzymes are the gloves).(22 votes)
- Out of curiosity, what is the name of the molecule he's drawing at? 4:10(2 votes)
- 1-bromo-1-fluoroethane(14 votes)
- what is stereochemistry?(3 votes)
- Stereochemistry is the study of the arrangements of atoms in space. It includes such topics as cis/tans isomerism, chair/boat conformations, and optical isomers — anything that involves the 3-D arrangement of atoms in space.(6 votes)
- Surely it is super imposable on its mirror at the beginning if you rotate it in the 3rd dimension? or is this just a model that only works in 2D?(2 votes)
- Not at all. Your right hand is a mirror image of your left hand. But no matter what you do in three dimensions, you're not going to fit a left-handed glove on your right hand or vice versa and have it fit. That is what superimposable means...are they identical? Of course not, otherwise gloves would be sold like most socks.(8 votes)
- does this mean that if there are no chiral atoms present, the molecule is not chiral ?(2 votes)
- No. Both responses are incorrect.
1. There are chiral molecules that have no chiral centers. Look up "allenes"
2. This is what I believe the second contributor meant. Cis and trans double bonds are sterogenic centers in that two different compounds are possible that are stereoisomers (diasteromers). However, that is not sufficient. You must have two cumulated alkenes (c=c bonds next to each other) with at least 2 substituents to have "axial" chirality.
There is also helical chirality. The DNA double helix is chiral. It is a right handed helix.
That is another topic however.(7 votes)
- I actually cannot understand why will the molecule be not superimposble (at). 5:36(2 votes)
- He is arguing, correctly, that the images are NOT superimposable because the carbon is chiral.(3 votes)
- Your definition of chirality is actually the definition of an enantiomer. They are the non superimposable mirror images. Diasteriomers are also chiral but are not mirror images.(0 votes)
- A chiral molecule as he defined it is accurate. A chiral molecule is an enantiomer of its mirror image. As well, a chiral molecule and its mirror image are enantiomers.
Diasteriomers have multiple stereocenters, each diasteriomer also often has an enantiomer. You're thinking of Meso compounds where a Diasteriomer isn't chiral since it doesn't have an enantiomer. Some Diasteriomers are indeed achiral (Meso compounds).
For instance, 2,3-dichlorobutane has 3 stereoisomers. You can draw it in a chiral form, where it has an enantiomer, then take the diasteriomer of it to find that it also has an achiral form. (You could also go the other way around, starting with the achiral form).(9 votes)
- I've heard people talk about the "chirality" of neutrinos, is it related to the chirality shown in this video?(1 vote)
- Not exactly.
All particles have a quantum mechanical "spin".
Particles that are "spinning" clockwise as they move forward are said to have a right-handed spin.
Particles that are "spinning" counterclockwise as they move forward are said to have a left-handed spin.
Neutrinos always have a left-handed spin, and antineutrinos have a right-handed spin.
In that sense, the two particles are chiral because their spins are nonsuperimposable mirror images of each other.(5 votes)
- At, when the mirror image of the first molecule is being drawn, the wedge does not change to a dash but instead remains as a wedge facing a different side. I was under the impression that it would be the case that the wedge would turn into a dash and vice versa in the mirror image. Is this not correct? And if so, why? 4:30(1 vote)
- The mirror in this case is perpendicular to the screen. Let's pretend that I'm standing with my arms out to the sides and facing a mirror; in my left hand I'm holding a bottle of milk, and in my right hand I'm holding a box of cereal. Now pretend that you're standing to my right and watching me. So the box of cereal (my right hand) is closer to you in real life. Now if you peek over into the image in the mirror, mirrored-me will be holding the box of cereal in mirrored-me's left hand. The hands that I'm holding the objects in have switched in mirrored-me, but the box of cereal that mirrored-me is holding will still be closer to you. This is just like what happened in the video. The wedge is still coming out of the page (i.e. still closer to you), but if you spin the right hand molecule 180 degrees (around its vertical CF axis) and try to overlay it on the left-hand molecule, you'll see that the wedge has become a dash - the CH3 and the H have "switched hands". Does that make sense?(3 votes)
Video transcript
If I were to draw a hand, and
let me just draw a hand really fast, so I'll draw
a left hand. It looks something like that. That is a left hand. Now, if I were to take its
mirror image, let's say that this is a mirror right there,
and I want to take its mirror image, and I'll draw the
mirror image in green. So its mirror image would look
something like this. Not exact, but you
get the idea. The mirror image of a left
hand looks a lot like a right hand. Now, no matter how I try to
shift or rotate this hand like this, I might try to maybe
rotate it 180 degrees, so that the thumb is on the other side
like this image right here. But no matter what I do, I will
never be able to make this thing look like
that thing. I can shift it and rotate it,
it'll just never happen. I will never be able to
superimpose the blue hand on top of this green hand. When I say superimpose,
literally put it exactly on top of the green hand. So whenever something is not
superimposable on its mirror image-- let me write this down--
we call it chiral. So this hand drawing
right here is an example of a chiral object. Or I guess the hand is an
example of a chiral object. This is not superimposable
on its mirror image. And it makes sense that it's
called chiral because the word chiral comes from the
Greek word for hand. And this definition of
not being able to be superimposable on its mirror
image, this applies whether you're dealing with chemistry,
or mathematics, or I guess, just hands in general. So if we extend this definition
to chemistry, because that's what we're
talking about, there's two concepts here. There are chiral molecules,
and then there are chiral centers or chiral-- well, I call
them chiral atoms. They tend to be carbon atoms, so
sometimes they call them chiral carbons. So you have these
chiral atoms. Now, chiral molecules are
literally molecules that are not superimposable on
their mirror image. I'm not going to write
the whole thing. You know, not superimposable--
I'll just write the whole thing. Not superimposable
on mirror image. Now, for chiral atoms, this is
essentially true, but when you look for chiral atoms within a
molecule, the best way to spot them is to recognize that these
generally, or maybe I should say usually, are carbons,
especially when we're dealing in organic chemistry,
but they could be phosphoruses or sulfurs, but usually are
carbons bonded to four different groups. And I want to emphasize
groups, not just four different atoms. And to kind of
highlight a molecule that contains a chiral atom or chiral
carbon, we can just think of one. So let's say that I have a
carbon right here, and I'm going to set this up so this
is actually a chiral atom, that the carbon specific is a
chiral atom, but it's partly a chiral molecule. And then we'll see examples
that one or both of these are true. Let's say it's bonded
to a methyl group. From that bond, it kind of
pops out of the page. Let's say there's a
bromine over here. Let's say behind it, there is a
hydrogen, and then above it, we have a fluorine. Now if I were to take the mirror
image of this thing right here, we have your carbon
in the center-- I want to do it in that same blue. You have the carbon in the
center and then you have the fluorine above the carbon. You have your bromine now
going in this direction. You have this methyl group. It's still popping out of the
page, but it's now going to the right instead of to
the left, So CH3. And then you have the hydrogen
still in the back. These are mirror images, if you
view this as kind of the mirror and you can see on both
sides of the mirror. Now, why is this chiral? Well, it's a little bit of a
visualization challenge, but no matter how you try to rotate
this thing right here, you will never make it exactly
like this thing. You might try to rotate it
around like that and try to get the methyl group over here,
to get it over there. So let's try to do that. If we try to get the methyl
group over there, what's going to happen to the other groups? Well, then the hydrogen group is
going-- or the hydrogen, I should say. The hydrogen atom is going to
move there and the bromine is going to move there. So this would be superimposable
if this was a hydrogen and this was a
bromine, but it's not. You can imagine, the hydrogen
and bromine are switched. And you could flip it and do
whatever else you want or try to rotate it in any direction,
but you're not going to be able to superimpose them. So this molecule right here is
a chiral molecule, and this carbon is a chiral center, so
this carbon is a chiral carbon, sometimes called
an asymmetric carbon or a chiral center. Sometimes you'll hear
something called a stereocenter. A stereocenter is a more general
term for any point in a molecule that is asymmetric
relative to the different groups that it is joined to. But all of these, especially
when you're in kind of in introductory organic chemistry
class, tends to be a carbon bonded to four different
groups. And I want to to stress that
it's not four different atoms. You could have had a methyl
group here and a propyl group here, and the carbon would still
be bonded directly to a carbon in either case, but that
would still be a chiral carbon, and this would still
actually be a chiral molecule. In the next video, we'll
do a bunch of examples. We'll look at molecules, try
to identify the chiral carbons, and then try to
figure out whether the molecule itself is--