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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Chlorine in the equatorial position

Methyl in the axial position

Both substituents in axial positions

Chlorine in the axial position

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Answer

In a cyclohexane chair, bulky groups want to be equatorial because that position keeps them away from the other axial hydrogens, reducing 1,3‑diaxial clashes. Chlorine is larger than a hydrogen but smaller than a methyl group, so it still prefers the equatorial side to avoid steric crowding. The methyl group is even bulkier, so it also strongly favors the equatorial position. If the chlorine were axial and the methyl equatorial, the chair would experience significant strain from both groups; flipping the chair so both are equatorial gives the lowest energy. Thus, the more stable conformation has both substituents in the equatorial positions.

Detailed Explanation

A chlorine atom prefers the equatorial position because it is larger than hydrogen and wants to avoid close contacts with neighboring axial hydrogens. Other options are incorrect because Students often think that a small methyl group can fit axially without issue, but it still creates 1,3‑diaxial interactions with nearby hydrogens; Choosing both chlorine and methyl axial would double the steric strain, because each axial group pushes against three neighboring axial hydrogens.

Key Concepts

Substituent Effects on Conformation

Topic

Cyclohexane Chair Conformations

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easy level question

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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 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 4

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 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

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

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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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