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

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All substituents in axial positions

All substituents in equatorial positions

A mix of axial and equatorial positions

Substituents randomly placed in either position

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Answer

In a cyclohexane chair, substituents that occupy the equatorial positions experience far fewer steric clashes than those in axial sites, so the most stable conformation places bulky groups equatorially. Axial substituents suffer 1,3‑diaxial interactions with other axial hydrogens, creating strain. Therefore, when choosing between two chair flips, the one that puts the larger group on the equatorial side is preferred. For example, a 2‑tert‑butylcyclohexane adopts the chair where the tert‑butyl group is equatorial, giving the lowest energy state.

Detailed Explanation

Equatorial positions keep the substituents farther from the ring's interior. Other options are incorrect because Misconception: All axial would be best; Mixing axial and equatorial is like balancing a seesaw.

Key Concepts

Chair conformation stability

Steric interactions in cyclohexane

Conformational analysis

Topic

Cyclohexane Chair Conformations

Difficulty

hard level question

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understand

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In a conformational energy diagram for cyclohexane, which of the following conformations corresponds to the highest potential energy due to steric strain?

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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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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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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 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

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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