Chiral Examples 2

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Chiral Examples 2

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Let's do a few more examples of seeing if either an atom or
an entire molecule is chiral.
So here I have a molecule.
Let's see if we can identify any chiral centers, or any
chiral atoms, or asymmetric carbons, all words for the
same thing, although I guess you could have chiral centers
that aren't necessarily carbon, but it tends to be
carbon most of the time, especially in Organic
Chemistry class.
So if we look here, the one that kind of jumps out, this
carbon right here is bonded to three
hydrogens and another carbon.
So this is obviously not going to be a chiral center.
It's bonded to three of the same group.
These three guys are all bonded to two hydrogens each,
so they're all bonded to two of the same group, so they
can't be chiral centers.
This carbon right here is bonded to three hydrogens,
once again, three of the same group, not going to be a
chiral center.
This one looks interesting.
It looks like it could be a good candidate it for a chiral
center, or a chiral carbon, or an asymmetric carbon.
Over here on the left, it's bonded to a methyl group, so
this is a methyl group, and here on the right, it's bonded
to a butyl group.
Over here, it's bonded to an OH, and then over here, it's
bonded to an H, so this is definitely a chiral carbon.
We could put a little asterisk here.
That's how they often denote that this is a chiral carbon.
And if this doesn't make sense to you, because you might say,
hey, Sal, look, this carbon is bonded to two other carbons.
Isn't that the same thing?
But the point here is that we're not looking at what
atoms it's directly bonded to.
We're looking at the groups that it's bonded to.
In this case, this hydrogen is a group and an atom.
Over here, it's an entire group.
It's an entire butyl group.
We have four carbons here.
We only have one over here.
Another way to think about it, we could have drawn this
molecule like this.
We could have had a carbon in the center, and maybe this
methyl group is popping out like this.
You have your CH3, and then you would have this hydrogen
coming out maybe in the plane, and then behind it, you would
have the butyl group.
So kind of the back leg of the tripod, you'd have a butyl,
and what is that?
That's C4H9, right?
That's six plus-- C4H9, so it's C4H9 in the back, and
then above it, you have your OH.
Above it, in a different color, you have your OH.
And when you look at it like this, it looks just like the
other chiral carbons that we had identified in actually the
last video.
It looks very similar to something like this.
And when you take its mirror image,
this is the same molecule.
Here, I kind of made it a little bit more three
dimensional, but if you take the mirror image of either
one, you're going to find that no matter how you try to
rotate it or shift it, you won't be able to superimpose
it on its mirror image for the same reasons
as the other ones.
And I challenge you to, if you can.
So this is a chiral carbon.
This is a chiral center, we could say.
Or we could even call it an asymmetric carbon.
It could be considered a stereocenter or
a stereogenic center.
All of those are valid things to call this
carbon right there.
And this is also a chiral molecule.
Now let's look at this blue example right here.
And if we wanted to name it, just so we get a little bit of
review, we could start at this fluorine right there: one,
two, three, four, five.
This is what?
This is 1, 3-difluorocyclopentane.
So that was a nice review of naming.
But let's think about whether we have any chiral centers
here and whether the molecule as a whole is chiral.
So the immediate ones that we can kind of dismiss-- and
actually let me get rid of this numbering because I don't
want you think that there are somehow three hydrogens there.
That was the number three hydrogen, number three carbon,
number two carbon, and so on so forth, But let me get rid
of them now that we've named the molecule.
I don't want to confuse how many hydrogens we have at any
of these points.
So let's look at the carbons.
Well, we could immediately dismiss that carbon, that
carbon, and that carbon, because each of those are
bonded to two hydrogens.
If we wanted to break it out, they would look like this.
So they're bonded to carbons, carbons, and then they're
bonded to hydrogens.
Now, these might be different groups.
These might be different types of alkane groups that it's
bonded to, so that doesn't necessarily throw it out of
the running.
But these two, the two hydrogens that it's bonded to,
are definitely the same atom, the same group.
We have an axis of symmetry through that atom, so it
cannot be a stereogenic center.
It cannot be an asymmetric carbon.
It cannot be a chiral center or a chiral atom, so we can
knock those guys out of the running.
But this guy and that guy seem pretty interesting.
Because if we were to break it out a little bit, you could
break it out like that and break it out like, so writing
a CH and actually show the bond to the hydrogen.
And this guy is bonded to one hydrogen, one fluorine.
And then if we were to work our way around the cycle, and
these cyclic molecules are a little bit-- it's sometimes a
little tricky to identify whether you're bonded to the
same group or different groups.
But actually, let me not make it too messy while we try to
figure this out.
To figure out whether it's bonded to the same group,
let's kind of take a walk around the cycle, around the
cyclopentane ring.
If we go this way, if we go on a counter-- we'll do it in
different color.
If we go in a counterclockwise direction from the carbon in
question, we're going to hit a CH2.
Then we're going to hit a CH.
So we're going to hit a CH2, then we're going to hit a CH.
If we go this way, we're going to hit a CH2 and then we're
going to hit another CH2.
So this guy is fundamentally-- this bond is bonded to a
different group than that bond up there is.
It's also bonded to a hydrogen,
also bonded to a fluorine.
So this is bonded to four different groups, so this is a
chiral carbon, so that is a chiral center.
Now, the exact same argument can be made for this carbon
right here.
You can make that exact same argument, that, look, if you
were to walk counterclockwise from this, you'd hit a CH2,
then a CH2.
If you were to go clockwise, you'd have CH2, then a CH,
which happens to be connected to a fluorine.
So you're actually going to see something different,
depending whether you're going down into that group or into
that group.
And then it's also bonded to a hydrogen and a fluorine, four
different groups.
This is also a chiral center.
Another way to think about it, and it's actually interesting
to compare it to this molecule up here, which was not chiral
and did not have a chiral center, this molecule up
here-- let me draw it a little different to make it a little
bit more clear.
So this one, I could draw it like this.
If you have the chlorine like that, over here, we thought
about this as a potential chiral center, and it's kind
of playing the same role as in that example down here, but
you see over here, this is not a chiral center because
there's actually an axis of symmetry for this molecule
that goes through that carbon.
So you can actually just draw an axis of symmetry that goes
exactly through that carbon.
The way I drew it, it's not completely neat, but you can
see that that is the reflection of that, if I were
to draw the bonds actually a little bit more symmetric.
Over here, if we try to do the exact same thing, if we try to
draw an axis of symmetry over here, if we try to draw an
axis of symmetry, we can make that bond to the fluorine go
through our axis of symmetry,, we'll see that that still is
not the reflection of this because we have
a fluorine up here.
We don't have a fluorine over here.
Now, we can do the same thing with this end.
If you try to do an axis of symmetry, fluorine up there,
no fluorine over here.
So each of these are definitely chiral centers,
while this carbon up here was not a chiral center.
Now, the next question is, well, this thing's got two
chiral centers, two chiral carbons.
It's probably a chiral molecule.
Everything else we've seen so far, if you had a chiral
center, you had a chiral molecule.
But let's take its mirror image.
To take its mirror image, let me clear out some real estate
over here, So let me clear out this.
Let me clear it out.
So what's the mirror image going to look like?
Let me draw first the mirror.
So the mirror image, you're going to have a
fluorine over there.
Then you're going to bond to a carbon, which is also bonded
to a hydrogen.
That's going to bond to a CH2.
That's going to bond to a CH.
That's the mirror image of that,
which bonds to a fluorine.
That's the mirror image of that.
And then you go down.
This is the mirror image of CH2 here.
This is the mirror image of this.
You connect them.
Now, these are mirror images of each other.
But they are also the exact same molecule.
I could just literally move this guy over to the right,
and it would be superimposed.
They are exactly the same.
So even though we have two chiral atoms, two chiral
carbons, the molecule as a whole is not chiral.
It is a non-chiral molecule.