The alkene shown is converted by (i) $BH X_{3}$ in THF and (ii) $H X_{2} O X_{2}$ , $NaOH$ into an alcohol (regiochemistry as in hydroboration-oxidation). Counting configurational stereoisomers (optical and geometrical together) of the constitution of that alcohol, how many are possible? Give your answer as an integer.

Numerical answer type, tolerance 0.5.

Answer: 8

The alkene is 1,5-dimethylcyclohexene. Boron adds to the unsubstituted alkene carbon, so oxidation gives 2,4-dimethylcyclohexan-1-ol. Its three ring stereocentres (C-1, C-2, C-4) are all distinct and the ring has no symmetry, so

2^{3} = 8

stereoisomers exist (confirmed by enumeration).

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Answer: 8

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