Chiral Examples 1

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Chiral Examples 1

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In the last video we learned a little bit about what a chiral
molecule or what a chiral carbon or a chiral atom is.
What I want to do in this video is go through a bunch of
examples and see if we can identify if there are any
chiral atoms and to also see if we're dealing
with a chiral molecule.
So let's look at our examples here.
So here I have, what is this?
This is chlorocyclopentane.
So the first question is do we have any chiral atoms?
And when we look at our definition that we thought of
chiral atoms, it all comes from this notion of handedness
and not being able to be superimposable on your mirror
image, but we said that they're usually carbons bonded
to four different groups.
Let's see, do we have any carbons here bonded to four
different groups?
Well, all the CH2's, they're bonded to another CH2
and then two H'2.
I could draw it like this: H and H.
So they're bonded to two of the same group, so none of
these CH2's are good candidates for being a chiral
center or chiral carbon.
They're both bonded to-- or all of them are bonded to two
hydrogens and two other very similar-looking CH2 groups,
although you have to look at the entire group
that it's bonded to.
But they're all definitely bonded to two hydrogens, so
it's not four different groups.
If we look at this CH right here, we could
separate it out like this.
We could separate the H out like this, and so since it's
bonded to a hydrogen.
This carbon is bonded to a chlorine, and then it's bonded
to-- well, it's not clear when you look at it right from the
get-go whether this group is different than this group.
But if you go around, if you were to split it half-way like
this, or maybe another better way to think about is if you
were to go around this molecule in that direction,
the counterclockwise direction, you would encounter
a CH2 group, and then you encounter a CH2 group, and
then you would encounter a third, and then you would
encounter a fourth CH2 group, then you would come back to
where you were before.
So you would encounter four CH2's and then you'd come back
to where you were before.
If you go in this direction, what happens?
You encounter one, two, three, four CH2's and you come back
to where you were before.
So all of this, this bottom group, depending on how far
you want to extend it, and this top group, are really the
same group.
So this is not a chiral center or not a chiral carbon.
It's not bonded to four different groups.
And this is also not a chiral molecule, because it does not
have a chiral center.
And to see that it's not a chiral molecule-- let me see
if I can backtrack this back to the way I
wrote it right before.
So you see that it's not a chiral molecule.
There's a couple of ways you could think about it.
The easiest way, or the way my brain likes to think about it,
is just to think about its mirror image.
Its mirror image will look like this.
So if that's the mirror, you would have a chlorine.
Then you have a CH, CH2, CH2, and you have a CH2, CH2, and
then you complete your cyclopentane.
Now, in this situation, is there any way to rotate this
to get this over there?
Well, if you just took this molecule right here and you
just rotated it 180 degrees, what would it look like?
Well, maybe a little over-- yeah, well, not quite 180
degrees, but if you were to rotate it so that the chlorine
goes about that far, you would get this exact molecule.
You would get something.
It would look a little bit different.
It would look like this.
Let me see if I can do it justice.
It would look like this.
You would have a CH2.
So let me let me do it up here where I have a
little bit more space.
If I were to rotate this about that far, I would get a CH.
You get the chlorine and then you have your CH2, and then
you have another CH2, CH2, and then you would
have your CH2 up there.
If you were to rotate this all the way around, or actually
this is almost exactly 180 degrees, it
would look like this.
And the only difference between this and this is just
how we drew this bond here.
I could have easily, instead of drawing that bond like
that, I could draw it facing up like that, and these are
the exact same molecule.
So this molecule is also not chiral.
So let's go to this one over here.
So what is this?
This is a bromochlorofluoromethane, just
to practice our naming a little bit.
But it's very clear that we are bonded to
four different groups.
All of the different groups, or the atoms in this case that
are bonded to this carbon, are different, so this carbon is a
chiral center.
And it should also be pretty clear that it is
also a chiral molecule.
If you were to take its mirror image, and this is very
similar to the example we did in the first video on
chirality, but its mirror image will look like this.
You have the bromine on the right now.
The hydrogen is still in back, and you have the
fluorine above it.
No matter how you try to rotate this thing, if you try
to get the bromine all the way over there, all the way to
that position, then the hydrogen would be in this
position and the chlorine would be in that position.
And no matter how you try to flip this around or rotate it
or shift it, you will never be able superimpose this molecule
on that molecule right there.
So that is a chiral center and this is a chiral molecule.
And there's a word for these two versions.
We're going to go into the naming of them later on.
It's a little bit more involved.
We'll have a whole separate video on it.
But these two versions of bromochlorofluoromethane, they
sometimes have different chemical properties.
And these are called enantiomers.
And enantiomers are just the mirror images.
Each enantiomer is a mirror image of each other, but they
are stereoisomers.
This is all just terminology.
Stereoisomers.
You're familiar with the word isomer, and isomer just means
that you have the same atoms in your molecule.
But then you have different types of isomers.
You have constitutional isomers that say, OK,
different things are connected to different things.
Stereoisomers, the same things are all
connected to the same things.
You have a carbon connected to only a fluorine, a chlorine
connected to the carbon, a hydrogen connected to the
carbon, a bromine connected to the carbon.
So all of the same things are connected to the same things,
but they're a three-dimensional
configuration.
That's where we're dealing with the stereo part.
Stereochemistry is the study of three-dimensional
chemistry, as essentially understanding the actual
three-dimensional structure of things.
So stereoisomers mean that we have the same constituents,
the same atoms. They have the same
connections to each other.
Bromine is still connected to carbon, which is still
connected to hydrogen.
That's all true over here.
But their three-dimensional
orientation is still different.
And in this case where they are mirror images of each
other, we call them enantiomers.
And I should probably make one clarification.
In the last few videos, I've been a little bit, you know,
sometimes I'll say configuration and sometimes I
use the word conformation.
So sometimes I'll use the word configuration and sometimes I
use the word conformation, and I actually should be a little
bit more, or I should have been a little bit more exact
about these.
When you're talking about a configuration, you're actually
talking about a different structure.
To go from one configuration to another configuration, you
would actually have to break bonds and kind
of reassemble them.
So these are different configurations.
Because in order for them to be able to be the same thing,
you would have to swap maybe the bromine and the hydrogen
in there where they are relative to the carbon, so
these are different configurations.
Confirmations are really just different shapes or different
orientations of the same molecule.
So when we talked about cyclohexane being in a boat,
so this is cyclohexane being in a boat conformation, or
this is cyclohexane being in a chair conformation, it's the
exact same molecule with the exact same connections.
We didn't detach any bonds or reattach any bonds.
They just flipped around a little bit.
So these are two different conformations.
These are two different configurations.
To go from one configuration to another, you have to
rearrange bonds.
Now let's look at this molecule over here.
Can we identify any stereocenters or chiral
carbons or chiral atoms?
And you have this carbon right here.
Let's see, this carbon right here is bonded to a chlorine,
a hydrogen, a bromine, and then another carbon.
So this is bonded to four different things, so this is a
chiral carbon.
Sometimes they put a little asterisk there.
If we look at this carbon right here you can-- well,
it's bonded to a fluorine and another carbon, but it's
bonded to two hydrogens, so it's not chiral.
It has two of the same things that it's bonded to.
You can even see a little axis of symmetry through it.
If you look at that, you can kind of flip it over, and it's
going to be the same thing.
But this one right here, that is a chiral center.
That is a chiral center, or chiral carbon, or chiral atom,
or a symmetric carbon.
You'll see it used in different ways.
And because this molecule has got that chiral center, you'll
see that if you were to take its mirror image, it would be
an enantiomer.
This is not superimposable on its mirror image.
We could even try to draw it.
And just so you know, you don't always have to do the
mirror image on the right side.
We can draw the mirror image on the left side.
So if we want to draw its mirror image, it
would look like this.
You would have a fluorine, carbon, carbon, chlorine.
You have your two hydrogens, and then you would have a
hydrogen here, and then you would have your bromine here.
No matter what you try to do, if you try to flip this around
or whatever, you will never be able superimpose this on top
of this, so these are enantiomers.
These are both stereoisomers relative to each other.
And either of these, regardless of which one you
pick, are chiral molecules.
I'm over the time that I normally want to go in the
video, so in the next video I'll do even more.