2-Isopropyl-5-methylcyclohexan-1-ol (menthol skeleton: OH on C1, isopropyl on C2, CH $_{3}$ on C5) has how many stereoisomers? Count enantiomers and diastereomers as distinct, and give the answer as an integer.

Numerical answer type, tolerance 0.5.

Answer: 8

C1, C2 and C5 are all stereocentres (each carries four different groups, because the ring paths differ). The molecule has no symmetry, so the number of stereoisomers is

2^{3} = 8

(four enantiomeric pairs: menthol, neomenthol, isomenthol and neoisomenthol and their mirror images).

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2-Isopropyl-5-methylcyclohexan-1-ol (menthol skeleton: OH on C1, isopropyl on C2, CH3​ on C5) has how many stereoisomers? Count enantiomers and diastereomers as distinct, and give the answer as an integer.

Answer: 8

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2-Isopropyl-5-methylcyclohexan-1-ol (menthol skeleton: OH on C1, isopropyl on C2, CH $_{3}$ on C5) has how many stereoisomers? Count enantiomers and diastereomers as distinct, and give the answer as an integer.