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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Chair conformation with the methyl group in the equatorial position

Boat conformation with the methyl group in the axial position

Chair conformation with the methyl group in the axial position

Twisted boat conformation with the methyl group in the equatorial position

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Answer

The most stable form of 1‑methylcyclohexane is the chair conformation with the methyl group in the equatorial position. In this shape the ring has minimal torsional strain and the methyl group avoids the 1,3‑diaxial contacts that occur when it is axial. A chair flip interchanges axial and equatorial positions, so the lowest‑energy form is the one where the methyl group ends up equatorial after the flip. This arrangement keeps the ring’s bonds in staggered alignment and reduces steric crowding, giving the molecule its greatest stability.

Detailed Explanation

When the methyl group is on the equatorial side, it stays farther away from the ring hydrogen atoms. Other options are incorrect because A boat shape always has more strain than the chair; Axial groups in the chair face 1,3‑interactions with hydrogens three atoms away.

Key Concepts

Chair and Boat Conformations

Torsional Strain

Ring Flipping

Topic

Cycloalkane Conformations

Difficulty

hard level question

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understand

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

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