Main content
Organic chemistry
Course: Organic chemistry > Unit 3
Lesson 3: Conformations of alkanesConformational analysis of butane
How to analyze the staggered and eclipsed conformations of butane.
Want to join the conversation?
- What is the difference between torsional strain and steric hindrance?(26 votes)
- Torsional strain is the increase in potential energy in the eclipsed Newman projection due to the repulsion between the electron clouds of 2 neighboring carbon atoms.
Steric hinderance is the strain that causes an increase in potential energy due to the repulsion between the electron clouds of 2 bulky substituents on carbons that are not neighboring .
If u look atof this video....steric hindrance is caused due to the repulsion of electron clouds of hydrogens attached to carbons 1 and 4 (not neighbors).....whereas torsional strain is caused due to the repulsion of electron clouds of hydrogens 2 and 3(which are neighbors) 0:56(28 votes)
- Are there similar terms for anti and gauche when talking about the eclipsed confirmation?(4 votes)
- Yes, but only when you have a unique functional group to differentiate them.
For example, ethane (C2H6), there would be no reason to differentiate between the eclipsed conformations (nor, the anti or gauche, which is why they are collectively referred to as staggered in that situation).
However, in butane (C4H10, the one in this video), the front and back carbons in the Newman projections each have a methyl group, and we use those to identify anti or gauche. This means we an also identify one unique eclipsed situation. If the methyl groups eclipse each other, it's referred to as the totally eclipsed conformation (or sometimes the cis conformation, but this is not a the same as cis-trans isomers, so keep that in mind). If the methyl groups eclipse a hydrogen, it's an eclipsed conformation.
The totally eclipsed conformation is even less stable/more potential energy state than the eclipsed conformations, which you can see in the potential energy graph for this video.(12 votes)
- I am not in school right now, but i am studying at home. I was on chemguide.co.uk and the practie problem said to draw but-2-en-1-ol, and i drew the -oh on the left, but they claim it must invariably be drawn on the right. Can anyone please tell me why, i would greatly appreciate it.(3 votes)
- It depends where the double bond is. In IUPAC naming, alcohol takes priority in naming over double bonds (i.e. you start counting carbons from the alcohol functional group). So, the alcohol needs to be on the end of the 4 carbon molecule and the double bond need to be between C2 and C3. Whether you start it on the right or the left doesn't matter as long as your double bond follows suit and switches sides as well.(3 votes)
- What does "degenerate" mean in this sense?4:05(1 vote)
- I believe it means that the two eclipse conformations have the same energy.(6 votes)
- What videos is he referring to at? 6:09(2 votes)
- He was talking about conformational analysis of ethane and propane
Those are the last two videos prior to this one-conformational analysis of butane.
In those videos, he found the energy cost between hydrogens, hydrogen-methane.(2 votes)
- Question about the eclipsed conformation that you showed around... Can it still be eclipsed if the methyl group on the top carbon is eclipsing one of the bottom hydrogens? I thought they had to be "eclipsing" the same substituents. 00:34(1 vote)
- Who does this voice over?(1 vote)
- Wait, the diagram assumes that the hydrogens on the methyl groups don't rotate, right?(1 vote)
- your corbon atoms are not in a zigzag order, i don't understand why. ? shouldn't they be in a zig zag pattern.?(1 vote)
- "and remember, in some earlier videos we talked about the energy cost associated with a pair of eclipsed hydrogens as 4 KJ/mol" I'm watching all these videos in order - this is the last video under Stereochemistry for CHEMICAL PROCESSES under MCAT. In which video(s) was this mentioned? The energy costs here were not mentioned in any of the videos I have seen thus far. 6:09
Thanks!(1 vote)
Video transcript
- [Voiceover] Here we
have the butane molecule, and this is carbon one, carbon two, carbon three, and finally carbon four. And if we stare down the
carbon two three bond, so here I'm rotating the molecule so we stare down the
carbon two three bond. This is a staggered confirmation of butane. And if we rotate the front carbon, and keep the back carbon stationary, I rotate 60 degrees, and we're going to get
an eclipse conformation. So I left it a little bit off so you can still see
the bonds in the back. So from the eclipse conformation of butane I rotate again, and we get a staggered conformation. Rotate another 60 degrees here, and we get an eclipsed conformation, and I'm gonna turn it to its side, so we can see how close
these methyl groups are in space. So if I rotate around, you can see with the model set, these hydrogens actually hit. So those hydrogens are close enough where they hit in the model set, and that's called steric hindrance, or steric strain. So back to the eclipsed
conformation of butane. If we rotate again, then we get a staggered conformation, we're gonna rotate again
to get another eclipsed again, slightly, a little bit off so you can still see the
bonds in the back here, and rotate one more time to get back to our staggered conformation. Here's an energy diagram
showing the different conformations we saw in the video. And these pictures are just stills from the actual video. We started with the staggered conformation of butane right here, which has a certain potential energy, and we went from this staggered conformation to this eclipsed conformation right here
by rotating 60 degrees. It takes energy to go from
the staggered conformation to this eclipsed conformation. The eclipsed conformation
is higher in energy, the eclipse conformation is less stable. Remember, the higher the potential energy, the less stable the conformation. The lower the potential energy, the more stable, so the staggered is more stable than the eclipsed. The energy difference between
these two conformations, let me go ahead and draw a dash line here. So this energy difference
between these two conformations turns out to be approximately 16 kilojoules per mole. So it takes energy to go from
the staggered conformation to this eclipse conformation. >From the eclipsed conformation we rotated 60 degrees and we got this staggered conformation. Notice this staggered conformation is a little higher in energy than our first staggered conformation. So if I draw a line right here, we can see there's an energy difference between our two staggered conformations. So the energy difference turns out to be approximately 3.8 kilojoules per mole. Going from this staggered conformation up here to this eclipse
conformation takes energy. So if I draw a line here,
so indicating the bottom, this energy difference is approximately 19 kilojoules per mole. So approximately 19 kilojoules per mole, and notice that this eclipse conformation is higher in energy. Let me change colors here. This eclipse conformation is higher in energy than
this eclipse conformation. So if we draw a line right here, we can see there's an energy difference of approximately three
kilojoules per mole. So this is the least stable conformation. This conformation, this
eclipse conformation has the highest potential energy. >From this eclipse conformation we could go to this staggered, so that's a decrease in potential energy. Notice this staggered has the same energy as this staggered conformation, so they are degenerate. Going from this staggered conformation up here to this eclipsed, it would take energy, and notice this eclipse conformation is the same in energy
as this one over here. So if I draw a line, you can
see it's the same energy. So these two are degenerate. These two eclipse
conformations are degenerate. And finally, going from
this eclipse conformation back down to our staggered conformation this is lower in energy. Now let's look at the conformations in more detail, and we'll start with this staggered conformation of butane. And let's go ahead and number the carbons. If this carbon is number one, as we called it in the video. That carbon is attached to this carbon, which is carbon number two. We stare down the carbon two, three bond to get
our Newman projection and in the video, you can't
see carbon number three, because carbon number
two is in front of it. But when you're drawing
a Newman projection, you represent the carbon in back, in this case carbon number three, with a circle. So this circle here represents
carbon number three. And finally, this would
be carbon number four. Let's think about the dihedral angle between our two methyl groups, so between this methyl group and this methyl group. Well, that would be 180 degrees so hopefully you can see there's 180 degrees
between our two groups. So the dihedral angle is 180 degrees. This conformation is called
the anti conformation. And the anti conformation is
lowest in potential energy, therefore, the anti-conformation is the most stable
conformation for butane. And that's because we take
these bulky methyl groups and we put them as far
away from each other as we possibly can. And all of our bonds are staggered, so if you think about these bonds here, everything is staggered. So that makes this the
most stable conformation. If we rotate 60 degrees
from the anti conformation, in the video, I kept the
back carbon stationary, and I rotated the front carbon. We would get this conformation. And this is an eclipsed conformation. So think about this bond eclipsing this bond and this hydrogen eclipsing this hydrogen. I didn't draw them as
being completely eclipsed, just so we could actually
see what's going on here. And remember, in some
of the earlier videos we talked about the energy cost associated with a pair
of eclipsed hydrogens, as four kilojoules per mole. So this energy cost is
four kilojoules per mole. We also talked about the energy cost from a methyl group eclipsing a hydrogen. So in the video on propane. And this was approximately
six kilojoules per mole, so six kilojoules per
mole for a methyl group eclipsing a hydrogen. That's the same situation
we have down here. A hydrogen and a methyl
group eclipsing each other, so this should be an energy
cost of six kilojoules per mole, too. If we add all of those up, so this would be four plus six is 10, plus another six is 16, we can see that's the energy difference between these two confirmations, so 16 kilojoules per mole higher. So this eclipsed conformation is higher in potential energy. Let's look at the other
eclipsed conformation. So that's the one over here. This is the highest in potential energy, so this must be the
least stable conformation for butane. If we look here, we
have a pair of hydrogens eclipsing each other, so that should be four kilojoules per mole. We have another pair
of hydrogens eclipsing each other so that's another
four kilojoules per mole. And then we have two
methyl groups eclipsing each other, so think about this bond, and this bond eclipsing each other, and these methyl groups being right on top of each other. So what's the energy cost associated with two methyl groups? A methyl group eclipsing a methyl group? We can figure that out, because we know the total energy cost is 19 kilojoules per mole. So this is what we don't know, so I'll call that X. So what is X? Well, if we add everything up, it should get 19, so 19 is the total. And we have four, and four, and X. So four plus four plus X is equal to 19. So obviously X is equal to 11. So 11 kilojoules per mole, is the energy cost associated with a methyl group eclipsing
another methyl group. So there's torsional strain there, but there's also steric strain, or steric hindrance,
which we saw in the video. These two methyl groups, the hydrogens can
actually get close enough to touch in the video when you're using a model set. And that is destabilizing. So if you have increased steric hindrance, that destabilizes your conformation. And that's why this conformation, this eclipsed conformation is the highest in potential energy. It's the least stable. So if I draw a line over here, just remember that this
eclipsed conformation is even higher in potential energy than this eclipsed conformation because of these two methyl groups
being so close together. And finally, let's look at
our staggered conformation. So our other staggered
conformation is right here. Notice this staggered conformation is higher in energy than our anti. So if we look at our methyl groups, we think about the dihedral angle, so if I think about the angle between these methyl groups here, that is 60 degrees, and we say that this is the gauche conformation, so let me go ahead and write this as the gauche conformation. And for the gauche conformation, this is a little bit higher in energy than for the anti-conformation. And that's because these two methyl groups are closer together in space. We don't really have to worry
about torsional strain here but we do have to worry
about steric hindrance. So these hydrogens on these methyl groups can get pretty close to each other in the gauche conformation, and that has a destabilizing effect, therefore having a higher potential energy for this conformation. So the gauche conformation,
while it's staggered, this is more stable than
our eclipsed conformations. The gauche conformation is not as stable as the anti-conformation
because these methyl groups are relatively close together in space.