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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equatorial

axial

trans

cis

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In the chair conformation of cyclohexane, substituents in the equatorial position are generally more stable. This is because equatorial groups lie flat against the ring, so they do not clash with other atoms. Axial groups point up or down, creating 1,3‑diaxial interactions that raise steric strain. For example, a methyl group prefers the equatorial orientation because it avoids contact with the six axial hydrogens on the same side. Thus, equatorial substituents experience less steric hindrance and are energetically favored.

Detailed Explanation

Equatorial positions give a substituent more room. Other options are incorrect because Axial groups are closer to the chair's own hydrogen atoms; Trans and cis describe how two groups are arranged relative to each other, not how they sit on the ring.

Key Concepts

Chair conformations of cyclohexane

Steric interactions

Molecular stability

Topic

Cyclohexane Chair Conformations

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medium level question

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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 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

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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