Learning Path
Question & Answer1
Understand Question2
Review Options3
Learn Explanation4
Explore TopicChoose the Best Answer
A
The stability decreases due to increased steric hindrance in the axial position.
B
The stability remains unchanged as both positions are equivalent.
C
The stability increases as the large substituent becomes more stable in the axial position.
D
The stability increases due to less steric hindrance overall.
Understanding the Answer
Let's break down why this is correct
Answer
In a cyclohexane, substituents in the equatorial position are far from the ring’s interior, so they experience little steric clash and the chair is stable. When the ring flips, the equatorial substituent moves to the axial position, bringing it close to the other axial hydrogens on the same side of the ring. This proximity creates 1,3‑diaxial interactions that raise the energy of the flipped chair, making it less stable. For example, a tert‑butyl group in the equatorial site will feel strong steric strain if it becomes axial during a flip, so the molecule prefers to stay in the conformation that keeps the bulky group equatorial. Thus, the presence of a large equatorial substituent makes the flipped chair significantly less stable than the original conformation.
Detailed Explanation
When the cyclohexane ring flips, the large substituent moves from the wide equatorial spot to the tight axial spot. Other options are incorrect because Many students think the two positions are the same because they see the ring flipped; Some believe the bulky group likes axial because it seems more exposed.
Key Concepts
Substituent Effects on Conformation
Ring Flipping Mechanism
Topic
Cyclohexane Chair Conformations
Difficulty
medium level question
Cognitive Level
understand
Practice Similar Questions
Test your understanding with related questions
1
Question 1In a molecule of 1-methylcyclohexane, which conformation minimizes steric hindrance and torsional strain while maximizing stability after a ring flip?
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2
Question 2When considering the ring flipping of 1,2-dimethylcyclohexane, what effect does this process have on the interactions of axial and equatorial substituents as represented in a conformational energy diagram?
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3
Question 3In a substituted cyclohexane, how does the axial position of a bulky substituent influence angle strain and overall stability compared to when it is in the equatorial position?
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4
Question 4When 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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5
Question 5In 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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6
Question 6In 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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7
Question 7In a chair conformation of cyclohexane, which statement best explains the implications of substituent positioning on molecular stability?
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8
Question 8When considering chair conformations of cyclohexane, which arrangement of substituents generally leads to the most stable conformation?
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9
Question 9In 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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