DAT Destroyer OC #230 (Nomenclature)

[zhngbrg]

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It asks to name a compound which I attached a picture of. I narrowed it down to

B) 2-bromo-5,5-dimethylcyclohexanol
C) 5-bromo-3,3-dimethylcyclohexanol

I chose C because it was my understanding that after taking priority of the parent molecule into account (in this case the alcohol), the numbering should give the lowest "sum" of the substituent numbers, so C would give 11 while B would give 12. However the answer key says the answer is B without much explanation. Can anyone please explain this to me?

Whoops the title says 230 but its actually question 231.

 

[tommyngu]

You are correct with your logic, but C is incorrect because the bromine is not on carbon 5. It would be 6-bromo-3,3-dimethylcyclohexanol. Simple mistake 🙂
Now if 6-bromo-3,3-dimethylcyclohexanol was an answer choice, I wouldn't know what other rule to use since both answer choices would give you a sum of 12. Hmmmmm