4. Alkanes and Cycloalkanes
Equatorial Preference
4. Alkanes and Cycloalkanes
Equatorial Preference
This is the #1 thing you need to know about cyclohexane. So let’s get right into it.
Determining the Best Position
1
concept
Equatorial Preference
4m
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- Blue = Axial. This position sucks, it’s really cramped up. Large groups can’t stand it.
- Green = Equatorial. This position is awesome. Large groups want to flip to this position.
Determining Equatorial Preference
We always want to draw our chairs with the largest groups equatorial. If they are axial, we need to flip the chair.
2
example
Draw the following chair in the most stable conformation.
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Don’t worry about drawing this problem out correctly on the first try, as long as you know how to flip it to the correct chair, that’s all that matters.
3
Problem
ProblemDraw the MOST STABLE conformation of cis-1-tert-butyl-4-methylcyclohexane.
A
B
C
D
Hint: If you don’t know what neopentyl is, it’s ok. Obviously it has 5 carbons, so keep that in mind when deciding equatorial preference!
4
Problem
ProblemDraw the LEAST STABLE conformation of trans-1-tert-butyl-3-neopentylcyclohexane.
A
B
C
D
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Additional resources for Equatorial Preference
PRACTICE PROBLEMS AND ACTIVITIES (36)
- Draw the most stable conformation of c. cis-1-tert-butyl-4-isopropylcyclohexane.
- Draw the most stable conformation of b. 3-isopropyl-1,1-dimethylcyclohexane.
- Draw the most stable conformation of a. ethylcyclohexane.
- Draw the two chair conformations of each compound, and label the substituents as axial and equatorial. In each...
- Draw the two chair conformations of each of the following substituted cyclohexanes. In each case, label the mo...
- The most stable form of the common sugar glucose contains a six-membered ring in the chair conformation with a...
- Use your models to do a chair–chair interconversion on each ring of the conformation of cis-decalin shown in [...
- [TABLE 3-6] shows that the axial–equatorial energy difference for methyl, ethyl, and isopropyl groups increas...
- Draw the most stable conformation of c. trans-1-tert-butyl-3-(1,1-dimethylpropyl)cyclohexane.
- Draw the most stable conformation of b. trans-1-tert-butyl-2-methylcyclohexane.
- Draw the most stable conformation of a. cis-1-tert-butyl-3-ethylcyclohexane.
- a. Draw both chair conformations of cis-1,4-dimethylcyclohexane, and determine which conformer is more stable....
- Draw the two chair conformations of each compound, and label the substituents as axial and equatorial. In each...
- Draw the two chair conformations of each compound, and label the substituents as axial and equatorial. In each...
- Draw the two chair conformations of each of the following substituted cyclohexanes. In each case, label the mo...
- Draw the two chair conformers for each of the following and indicate which conformer is more stable: f. cis-1-...
- Draw the two chair conformers for each of the following and indicate which conformer is more stable: c. trans-...
- Bromine is a larger atom than chlorine, but the equilibrium constants in Table 3.9 indicate that a chloro subs...
- Draw the most stable conformer of the following molecule. (A solid wedge points out of the plane of the paper ...
- Which has a higher percentage of the diequatorial-substituted conformer compared with the diaxialsubstituted c...
- Using the data in Table 3.9, calculate the percentage of molecules of cyclohexanol that have the OH group in a...
- The most stable form of glucose (blood sugar) is a six-membered ring in a chair conformation with its five sub...
- Draw two chair conformations of the molecules below. Indicate which is most stable. (a)
- For each pair of conformations you drew in Assessment 3.41, indicate which is most stable.
- (••) For each pair of conformations shown, choose which is most stable. If both are equally stable, then write...
- (••) For each pair of conformations shown, choose which is most stable. If both are equally stable, then write...
- (•••) For each structure shown, draw the two chair conformations and choose which is most stable. Be sure that...
- (•••) For each structure shown, draw the two chair conformations and choose which is most stable. Be sure that...
- Draw the two chair conformers for each of the following and indicate which conformer is more stable: b. trans-...
- Draw the two chair conformers for each of the following and indicate which conformer is more stable: d. cis-1,...
- a. Draw the more stable chair conformer of cis-1-ethyl-2-methylcyclohexane.
- c. Which compound is more stable: cis-1-ethyl-2-methylcyclohexane or trans-1-ethyl-2-methylcyclohexane?
- c. Which compound is more stable: cis-1-ethyl-2-methylcyclohexane or trans-1-ethyl-2-methylcyclohexane?
- For each of the following structures, draw the most stable chair conformer. a. b.
- b. For each pair, indicate which conformer is more stable.
- When a pyranose is in the chair conformation in which the CH2OH group and the C-1 OH group are both in axial p...