All right, guys. So in these videos, I'm going to teach you how to use free energy in kilojoules per mole to calculate the exact percentages of each conformation that you would get of a cyclohexane. Again, these videos might be beyond the scope of what your professor wants you to know for your test. So I'm going to leave it up to you to if you need to know this or not. You've been warned, so it's time to get into this. It turns out that we can use that delta G value that we get from our A values to calculate those exact percentages at any given temperature. Now the way we do this is through the Gibbs free energy equilibrium constant equation. Just so you guys know, if this equation looks familiar, it's not unique to this type of problem. In fact, pretty much any process that you can describe a free energy difference in can, you can determine an equilibrium through this equation. So this is a very important equation for all of chemistry, not just for cyclohexanes. Okay? Now as you can see, what it says is that let's just go through one term at a time. It says that the delta G for the change in free energy is equal to the negative R. Now remember that R is the gas constant that we used to use in general chemistry and there were 2 different values of R that we used to use. Just note that the one we're using is in joules per mole, so that's 8.134. That's going to be important in a second. Then temperature, temperatures in Kelvin. Remember that I mean it's been a while since we dealt with temperature, but remember that 0 degrees Celsius is equal to 273.15 degrees Kelvin. That's going to be a conversion that we have to use in a little bit. Then you're going to multiply that by the natural log of the equilibrium constant. Well, in order to solve any of these problems for percentages, we need to know the value of the equilibrium constant. Because equilibrium constant by definition tells you what's your products over your reactants. I need to know that fraction. If we go ahead and we solve for K_{E}, I did the math for you. Don't worry. What we get is that the K_{E} is equal to the negative delta G over the R times the T, all to the e. If we can just plug in these variables, we're going to get the equilibrium constant. Now we know what R is. We know what T is. Your calculator tells you what E is. All we need is negative delta G. Do we have a way to find that? Yes, guys. That's through our A values. Our A values tell us what the free energy changes as we go axial. Awesome. Now I do want to make one note of the delta G. Notice that this is negative delta G. But everything that we solved when we're doing A values, we were actually solving for positive delta G because we were actually looking at the less stable one. We're looking at how much energy do we have to put into the system to go to axial. When we use this equation, we're actually going to be inputting the positive delta G here and that's fine. What we're going to be getting is a number that describes basically how we're going to that less stable value. So then over here, what we have is that then we get that K_{E} and now we can solve for the percentages using the definition, products over reactants. Once we get that positive K_{E} number, that positive K_{E} number means that we're actually going towards the favored direction. I'm not sure if you guys remember but if you have a K_{E} over 1, that means you're going to the more favored direction. I'm just telling you guys right now, if we use a positive number for delta G, we're going to get also a positive number. I'm sorry. We're going to get a number that's above 1 for K_{E}. We're going to get this greater than 1. What that means is that our definition of K_{E} has to be the products over the reactants, meaning the more favored conformation over the less favored. Just letting us know that the way that we've arranged this equation, the way that your textbook does it, is that it always does the more favored over the less favored. Meaning that when you get this positive value, it's going to tell you what percentage you're going to have of the equatorial. And then that minus 100 will be your axial. Now here it says that K_{E} is equal to X over one over X. That just has to do with the definition of equilibrium constant. How K_{E} is what your X is what you're making. That's your product. So then one minus whatever you made would be your reactants. Then we don't really want K_{E} here. We want X because we're really trying to figure out how much of this product we're going to get. So if we solve for X, I did that for you. What you're finally going to get is that X is equal to K_{E} over K_{E}+1. If you want to put it in a percentage term, it's times 100. Now that was a ton of words that I just said, a lot of numbers and symbols. I do not need you guys to perfectly understand this as much as I just need you to memorize it and know how to use it. If your professor wants you to solve this on your exam, then these equations should be in your mind. You should have memorized this equation. You should have memorized the definition of K_{E} or how to solve for X. Now we're going to focus on the actual working part, on the actual part that we determine percentages which is so cool. I'm a huge Orgo nerd as you guys know. This is fun. Getting to determine the exact percentage of each cyclohexane. This first one will be a worked example and we'll go ahead and start off with this first one. I'm just going to pause the video and then we'll come back and we'll solve this one together.

- 1. A Review of General Chemistry5h 5m
- Summary23m
- Intro to Organic Chemistry5m
- Atomic Structure16m
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- Octet Rule12m
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- Skeletal Structure14m
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- Condensed Structural Formula15m
- Degrees of Unsaturation15m
- Constitutional Isomers14m
- Resonance Structures46m
- Hybridization23m
- Molecular Geometry16m
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- 2. Molecular Representations1h 14m
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- 4. Alkanes and Cycloalkanes4h 19m
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- Equatorial Preference14m
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- A-Values17m
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- 16. Conjugated Systems6h 13m
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- 20. Phenols55m
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- 22. Carboxylic Acid Derivatives: NAS2h 51m
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- 23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
- 24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
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- 25. Condensation Chemistry2h 9m
- 26. Amines1h 43m
- 27. Heterocycles2h 0m
- Nomenclature of Heterocycles15m
- Acid-Base Properties of Nitrogen Heterocycles10m
- Reactions of Pyrrole, Furan, and Thiophene13m
- Directing Effects in Substituted Pyrroles, Furans, and Thiophenes16m
- Addition Reactions of Furan8m
- EAS Reactions of Pyridine17m
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- 28. Carbohydrates5h 53m
- Monosaccharide20m
- Monosaccharides - D and L Isomerism9m
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- Mutarotation11m
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- 29. Amino Acids3h 20m
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- Reactions of Amino Acids: Esterification7m
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- 30. Peptides and Proteins2h 42m
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- 32. Lipids 2h 50m
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- Negishi Coupling Reaction16m
- Buchwald-Hartwig Amination Reaction19m
- Eglinton Reaction17m

# A-Values - Online Tutor, Practice Problems & Exam Prep

To calculate the percentages of cyclohexane conformations using Gibbs free energy, apply the equation ΔG = -RT ln(KE). Here, R is the gas constant (8.314 J/mol·K) and T is temperature in Kelvin. The equilibrium constant (KE) is derived from the ratio of products to reactants, indicating favored conformations. A KE greater than 1 suggests a preference for equatorial over axial conformations. The final percentage of equatorial conformations can be calculated as x = KE / (KE + 1) × 100, where x represents the favored conformation.

Now that we know how to calculate the difference in flip energy, we can plug that information into the famous Equilibrium Constant equation to determine exact K_{e} of the reaction.

### Calculating Chair Equilibrium

#### Video transcript

Gas Constant correct number:8.**314**

Once we have the Ke of the equilibria, we can solve for x, which will be the percentage of my most favored chair.

Estimate the equilibrium composition of the chair conformers of the following cyclohexanes at room temp:

*cis*-1,3-diethylcyclohexane

#### Problem Transcript

Did you remember to use the correct Gas Constant number?! (*8.314)*

Estimate the equilibrium composition of the chair conformers of trans-1-methyl-3-phenylcyclohexane at room temperature.

#### Problem Transcript

*Note:* The correct value for methyl should be **7.6**, not 4.2

With that, the correct answer should be closer to __88__% / __12__% for the percentage of both chairs using the correct value for R (8.314). Hope that makes sense!

## Do you want more practice?

More sets### Here’s what students ask on this topic:

What are A-values in organic chemistry?

A-values, or axial values, are numerical values that represent the free energy difference between axial and equatorial positions in cyclohexane conformations. These values help predict the stability of different substituents in cyclohexane rings. A higher A-value indicates a greater preference for the equatorial position due to steric hindrance in the axial position. Understanding A-values is crucial for determining the most stable conformation of substituted cyclohexanes.

How do you calculate the percentage of equatorial and axial conformations in cyclohexane?

To calculate the percentage of equatorial and axial conformations in cyclohexane, use the Gibbs free energy equation: $\mathrm{\Delta G}=-\mathrm{RT}ln(K$_{E} _{E} is derived from the ratio of products to reactants. The percentage of equatorial conformations is calculated as $x=\frac{K}{}$_{E}_{E}

Why is the equatorial position more stable than the axial position in cyclohexane?

The equatorial position in cyclohexane is more stable than the axial position due to reduced steric hindrance. In the axial position, substituents experience 1,3-diaxial interactions with hydrogen atoms on the same side of the ring, leading to increased steric strain. In contrast, the equatorial position allows substituents to be more spread out, minimizing these interactions and resulting in a more stable conformation.

How does temperature affect the equilibrium between axial and equatorial conformations in cyclohexane?

Temperature affects the equilibrium between axial and equatorial conformations in cyclohexane by influencing the Gibbs free energy change (ΔG). As temperature increases, the equilibrium constant $K$_{E} can shift, altering the ratio of equatorial to axial conformations. Higher temperatures generally increase the energy available to overcome steric hindrance, potentially leading to a higher proportion of axial conformations. However, the exact effect depends on the specific ΔG values for the substituents involved.

What is the significance of the Gibbs free energy equation in determining cyclohexane conformations?

The Gibbs free energy equation $\mathrm{\Delta G}=-\mathrm{RT}ln(K$_{E} _{E}, which indicates the ratio of equatorial to axial conformations. By knowing ΔG, which can be derived from A-values, and the temperature, one can determine the favored conformation and calculate the exact percentages of each conformation. This is crucial for understanding the stability and behavior of substituted cyclohexanes.

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