Learning Path
Question & Answer1
Understand Question2
Review Options3
Learn Explanation4
Explore TopicChoose the Best Answer
A
The molecule is more stable with the bulky substituent in the equatorial position.
B
The molecule is equally stable regardless of the substituent position.
C
The molecule is more stable with the bulky substituent in the axial position.
D
The stability cannot be determined without additional information.
Understanding the Answer
Let's break down why this is correct
Answer
A bulky group on the equatorial side of a cyclohexane chair meets fewer neighboring hydrogens, so it avoids the 1,3‑diaxial clashes that happen when the same group sits axially. Because those clashes create steric strain, the axial isomer is higher in energy and less stable. Thus, the molecule with the bulky substituent equatorial is more stable than the axial version. For example, 1‑methylcyclohexane is more stable when the methyl group is equatorial, giving a lower‑energy chair than when the methyl is axial. The energy difference is about 2–3 kcal/mol, making the equatorial form the preferred conformation.
Detailed Explanation
When a large group sits in the equatorial spot, it sits lower and spreads out, so the ring has less crowding. Other options are incorrect because Thinking the positions are equal ignores the fact that axial places a bulky group directly up against many other parts of the ring; It sounds reasonable that the upright axial spot gives more room, but it actually forces the bulky group into close contact with neighboring atoms.
Key Concepts
Energy Comparison of Conformations
Topic
Cyclohexane Chair Conformations
Difficulty
easy 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?
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2
Question 2In 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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3
Question 3When 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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4
Question 4In 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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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 chair conformation of cyclohexane, which statement best explains the implications of substituent positioning on molecular stability?
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7
Question 7In 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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