Learning Path
Question & Answer1
Understand Question2
Review Options3
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Explore TopicChoose the Best Answer
A
The axial position increases angle strain and decreases stability.
B
The axial position decreases angle strain and increases stability.
C
The axial position has no effect on angle strain or stability.
D
The axial position decreases angle strain but decreases stability.
Understanding the Answer
Let's break down why this is correct
Answer
Bulky groups in a cyclohexane ring prefer the equatorial orientation because the axial position forces the bond to tilt toward the ring, creating a 60‑degree torsion that pulls the substituent into a crowded space and increases angle strain. In the axial position, the substituent’s bonds are forced into a gauche-like arrangement with neighboring hydrogens, raising steric hindrance and raising the ring’s overall energy. When the same group is placed equatorially, it lies farther from the ring’s interior, minimizing steric clashes and keeping bond angles closer to the ideal 109. 5°, so the ring experiences less angle strain and is more stable. For example, a tert‑butyl group in 1‑tert‑butylcyclohexane prefers the equatorial position, making the compound about 2–3 kcal/mol more stable than its axial isomer.
Detailed Explanation
An axial substituent sits directly above or below the ring, forcing bonds to bend toward the center. Other options are incorrect because Many think axial makes the ring easier to hold, ignoring that the axial group forces adjacent hydrogens to crowd, raising strain; The misconception is that axial and equatorial have the same effect.
Key Concepts
Substituent Positioning
Angle Strain
Topic
Cycloalkane Conformations
Difficulty
medium level question
Cognitive Level
understand
Practice Similar Questions
Test your understanding with related questions
1
Question 1In a cyclohexane derivative with two substituents, one methyl group at the 1-position and another at the 3-position, which configuration will be observed if the methyl at the 1-position is axial and the methyl at the 3-position is equatorial?
mediumChemistry
Practice
2
Question 2When analyzing a cyclohexane derivative with a bulky substituent in the axial position, what effect does ring flipping have on the stability of the molecule?
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Practice
3
Question 3In a substituted cyclohexane where a large substituent is present in the equatorial position, what is the likely impact on the molecule's stability when the ring undergoes flipping?
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Practice
4
Question 4In a cyclohexane derivative featuring both a chlorine atom and a methyl group, which substituent position (axial or equatorial) would likely lead to a more stable chair conformation?
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Practice
5
Question 5In a cyclohexane derivative with a bulky substituent in the equatorial position, how does this affect the molecule's overall stability compared to when the same substituent is in the axial position?
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Practice
6
Question 6In the chair conformation of cyclohexane, substituents in the ____ position are generally more stable due to reduced steric interactions compared to those in the axial position.
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Practice
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