Problem

The following questions relate to a cyclohexane ring depicted in the chair conformation sh...

The following questions relate to a cyclohexane ring depicted in the chair conformation shown.

(a) Is a methyl group at C-6 that is “down” axial or equatorial?


(b) Is a methyl group that is “up” at C-1 more or less stable than a methyl group that is up at C-4?


(c) Place a methyl group at C-3 in its most stable orientation. Is it up or down?


Sample Solution (a) First indicate the directional properties of the bonds to the ring carbons. A substituent is down if it is below the other substituent on the same carbon atom. A methyl group that is down at C-6 is therefore axial.

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