Destroyer O-chem #125

[RFDMD]

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Why isn't the answer C, which would give the lowest total subsititution?

Answer is B.... 2-bromo-5,5-dimethylcyclohexanol (Total sub=12)

C is 5-bromo-3,3-dimethylcyclohexanol (total sub=11)


🙄

 

[issa]

Why isn't the answer C, which would give the lowest total subsititution?

Answer is B.... 2-bromo-5,5-dimethylcyclohexanol (Total sub=12)

C is 5-bromo-3,3-dimethylcyclohexanol (total sub=11)


🙄

because the OH has higher priority than CH3

 

[RFDMD]

I agree the OH has the higher priority. It just depends on which way you start around the ring....

If started CW then the total sub's add to be 11,

if CCW then they add up to be 12....

or am I missing something besides a good night's rest...? 😴

OK, Dr. Romano just explained it to me...

The lowest substituent possible get's the priority... Not just total of substituents....

Thanks, Doc....