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

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Equatorial substituents are more stable due to reduced steric hindrance.

Axial substituents are always more stable regardless of the size.

Substituents can freely rotate between axial and equatorial positions without energy cost.

Only bulky substituents affect the stability of chair conformations.

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Answer

In a chair conformation, substituents that are axial sit directly above or below the ring and clash with other axial hydrogens, creating 1,3‑diaxial interactions that raise the energy. Because the equatorial position opens up to the rest of the molecule, it has less steric strain and is therefore lower in energy. Thus a substituent prefers the equatorial orientation whenever possible. For example, 1‑methylcyclohexane adopts the chair where the methyl group is equatorial, because the axial isomer would suffer severe steric hindrance and be less stable.

Detailed Explanation

When a group sits in an equatorial spot, it is farther from the other atoms in the ring. Other options are incorrect because The belief that axial groups are always better ignores that axial groups touch nearby atoms; Changing a group from axial to equatorial is not a free move.

Key Concepts

Cyclohexane Chair Conformations

Substituent Positioning and Sterics

Molecular Stability

Topic

Cyclohexane Chair Conformations

Difficulty

medium level question

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understand

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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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Question 2

In a substituted cyclohexane with a bulky tert-butyl group and a smaller ethyl group, which configuration minimizes steric hindrance and maximizes stability in the chair conformation?

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Question 3

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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Question 4

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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Question 5

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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Question 6

Arrange the following conformational changes of cyclohexane from least to most stable: A. Chair conformation, B. Twist-boat conformation, C. Boat conformation, D. Half-chair conformation.

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Question 7

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

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Question 8

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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