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pnoybballin

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The most stable conformation of cis-1,2,4-trimethylcyclohexane has which of the following orientations for the three methyl groups?

A. The chair conformations with 3 equatorial methyls ad 0 axial methyls
B. The chair conformations with 2 equatorial methyls ad 1 axial methyls
C. The chair conformations with 1 equatorial methyls ad 2 axial methyls
D. The chair conformations with 0 equatorial methyls ad 3 axial methyls

The answer is B but why wouldn't it be A?
 
Because A would change the name of the compound. In order to be cis, 2 methyl groups must be oriented in the same direction. I'm fairly certain this is correct...
 
If all of the methyl groups were in the equatorial conformation there would be more steric hindrance caused by the closer hydrogens. Axial conformation of one of those groups would reduce the steric hindrance between them.
 
If all of the methyl groups were in the equatorial conformation there would be more steric hindrance caused by the closer hydrogens. Axial conformation of one of those groups would reduce the steric hindrance between them.

This isn't quite true. You're talking about gauche butane interactions, but they are not applicable to this discussion. The compound is cis-1,2,4-trimethylcyclohexane. All 3 methyl groups are cis to each other, so they are all on the same face. So we have two possible chair conformations:

first: at the 1 position, we're equatorial, and the two position, we're axial, and at the 4 position we're axial (because if you take a single face of a chair conformation of a cyclohexane, the substituents on that face will alternate between axial and equatorial. so if we pick equatorial at the 1 position, whatever's on that face at the 2 position is axial, at the 3 position it's equatorial, at 4 it's axial, at 5 it's equatorial, and at 6 it's axial)

second: at the 1 position, we're axial, at the two position we're equatorial, and at the 4 position we're equatorial.

these are the only two possibilities we have, because we are limited by the fact that they tell us that the methyl groups are all on the same face of the molecule.

so first of all, that eliminates A as an answer choice because it isn't physically possible to have cis-1,2,4-trimethylcyclohexane exist in an all equatorial conformation since the chair form would place either one or two of those groups axial. Now, if we had the 1,2,4-trimethylcyclohexane where the 2 and 4 were cis to each other and the 1 methyl was trans to the other two methyls, then yes, the preferred conformation is the all-equatorial conformation.

so our answer is either b or c. B, which is the second of the two possibilities I mentioned above, is correct because it places the most number of groups equatorial. Placing two groups axial, as in the first possibility I mentioned, is extremely unfavorable, because there is a Me/Me 1,3-diaxial interaction between the methyl groups at positions 2 and 4. Placing just 1 group axial is better, since the primary steric interaction is the Me/H 1,3-diaxial interaction.

The point sharing was making about having two methyl groups in adjacent equatorial positions is, in fact, an unfavorable steric interaction. However, it cannot apply to this problem because the only way you can have two adjacent methyl groups both in equatorial positions is if they are trans to each other. In addition, if you did have a case where there were two methyl groups in adjacent positions trans to each other, ring flipping to put both of them axial would only introduce more strain on the molecule by creating 1,3-diaxial interactions.

lemme know if you have questions, I'll have to check what I wrote in the morning to make sure it's coherent
 
Short answer:

You can't have cis configuration and has a 1,2 equatorial configuration. Do you have a molecular model set? This is very easy to visualize if you do.
 
I found that when first approaching problems like this it's very easy (but wrong) to think, "okay, all cis therefore all equatorial (or all axial)"

the way i learned: the cis refers to the direction of the substituent on the chair conformation

when you draw out a chair conformation, say you place the 1st methyl group up (which would be axial), the next methyl would also have to be up (to make it cis, and therefore it would be equatorial. the 3rd methyl group (on the 4th carbon) would also have to be up and being on the 4th carbon up would be equatorial... the opposite is also possible being equatorial first, then axial, and axial (respectively)


hmm... after reading my explanation i see that I may have confused you more than helped, so if you're not comfortable with chair conformations in your head (or drawing them) this might not be the best advice (although it's correct)
 
img0122n.jpg


I hope that clarifies it a bit, both of those are the molecule you wrote out, except i didn't specifiy that everything BUT the circled are just hydrogens. In one case there are 2 equatorial and 1 axial (more stable) and the other there are 2 axial and 1 equatorial (less stable)

however in both cases either all the methyl groups (circled) are pointing up, or all down (hence they are all cis)

hope that helps
http://img441.imageshack.us/my.php?image=img01221.jpg
 
so B and C can be the correct answers.. i think the Opener made a mistake in typing up the question...
 
so B and C can be the correct answers.. i think the Opener made a mistake in typing up the question...

No, the only right answer is B. The question is asking which is more stable, and having 2 eq and 1 ax is more stable than 1 eq and 2 axial

they are both *possible* configurations but only one is most stable
 
Because A would change the name of the compound. In order to be cis, 2 methyl groups must be oriented in the same direction. I'm fairly certain this is correct...

that's why. they're all cis, so they have to be on the same side of the plane. based on the carbons these methyls are on, you cannot have all 3 be equatorial and still be on the same side of the plane (cis). you need to draw it in chair confirmation to visualize this. once you draw it out once, you'll be able to picture it in your head.

as the person above said, C is definitely wrong because that is not the most stable form. it is A FORM of the molecule, but not the most stable. the most stable form is the one with the most equatorial substituents without changing the name of the molecule.
 
Related question:

If cis-1,2,4-trimethylcyclohexane means all three methyl groups are facing the same direction, what would trans-1,2,4-trimethylcyclohexane look like? For some reason, I though the cis, or trans only referred to to substituents.
 
I think in that case, because you have 3 substituents you can't just say trans, because they obviously can't all 3 be in different positions. i think it would have to be named something like cis-1,4-trans-2-trimethylcyclohexane indicating that the 1 and 4 are cis and the 2 is trans to them. The naming might be incorrect (been a while since i've done ochem nomenclature) but i'm pretty sure you can't just have trans-1,2,4-tri... so to answer your question, that can't be drawn...
 
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