The cyclohexane ring is the parent chain; either methyl-bearing carbon could be carbon #1.
The octane chain is the parent; the lowest number sequence is generated when the chlorine is bonded to carbon #2.
The cyclohexane ring is the parent; the lowest number sequence is generated when the geminal dimethyl group is bonded to carbon #1, proceeding counter-clockwise around the ring.
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click on the button to view the parent chain and the correct numbering sequence.