📚 Learning Guide
Cyclohexane Chair Conformations
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In 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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Choose 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

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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 1

In 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 2

When 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 3

In 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 4

When 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 5

In 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 6

In 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 7

In a chair conformation of cyclohexane, which statement best explains the implications of substituent positioning on molecular stability?

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8
Question 8

When considering chair conformations of cyclohexane, which arrangement of substituents generally leads to the most stable conformation?

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9
Question 9

In 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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