Of all the possible cyclooctanes that have one chloro substituent and one methyl substituent, which ones do not have any asymmetric centers?

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Of all the possible cyclooctanes that have one chloro substituent and one methyl substituent, which ones do not have any asymmetric centers?

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Answer 1 · 2015-09-24T15:19:22

The only isomers without chiral centres are 1-chloro-1-methylcyclohexane, cis-1-chloro-5-methylcyclohexane, and trans-1-chloro-5-methylcyclohexane.

Explanation:

In order for the centres to be achiral, they must have a plane of symmetry passing through them.

The only possibilities are

Cyclooctane

The first structure, 1-chloro-1-methylcyclohexane, has a vertical plane of symmetry that includes, #C-5#, #C-1#, #CH3#, and #Cl#.

The other two structures, cis- and trans-1-chloro-5-methylcyclohexane, have a vertical plane of symmetry that includes #C-1#, #C-5#, and the wedged and dashed bonds that are directly attached to them.

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Of all the possible cyclooctanes that have one chloro substituent and one methyl substituent, which ones do not have any asymmetric centers?

1 Answer

Explanation:

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