(-)-Menthol: spot the stereochemistry flaw

Single question

Final step of the Takasago menthol process: hydrogenate (-)-isopulegol to (-)-menthol with H2 over a Ni catalyst. The reactant, catalyst, and conditions match the published route. Check the absolute configuration on the product.

Stereoretention during alkene hydrogenation

Takasago menthol process

Reading absolute configuration on polysubstituted cyclohexanols

Find the flaw

Click the step that contains the flaw, or pick “No flaw” if you think every step is correct.

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