In a chair conformation of cyclohexane, when a substituent is placed in an equatorial position, it is always more stable than when it is in an axial position.

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In a cyclohexane chair, each carbon can hold a substituent either pointing outwards (equatorial) or up and down (axial). Axial groups clash with other axial hydrogens on the same side of the ring, creating 1,3‑dipolar steric strain that raises the energy. Equatorial groups avoid these close contacts because they lie in the plane of the ring and are farther from other substituents. Thus an equatorial substituent is lower in energy and more stable. For example, a methyl group on carbon 1 prefers the equatorial position over the axial one because the axial position would force it into a steric clash with the axial hydrogens on carbons 3 and 5.

Detailed Explanation

When a group sits in an equatorial spot, it can spread out and avoid bumping into other axial hydrogens. Other options are incorrect because Some students think large groups can do better in axial positions.

Key Concepts

Chair Conformations

Steric Hindrance

Substituent Effects

Topic

Cyclohexane Chair Conformations

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easy level question

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understand

Practice Similar Questions

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Question 1

In 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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Question 2

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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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

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

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Question 8

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

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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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