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The stereochemistry effect of eugenol, cis-isoeugenol and trans-isoeugenol on their catalytic hydrogenation by Ni/g-Al₂O₃ catalyst was investigated. In this investigation, the catalyst is prepared by impregnation of Nickel into solid of γ-Al₂O₃ in methanol as a solvent. The calcination process, which is followed by reduction, is performed on Muchalal reactor at 400 ^oC. After that, the catalytic hydrogenation is carried out under hydrogen gas atmosphere by mixing 10 mL sample and 0.5 g Ni/g-Al₂O₃ catalyst at 200 ^oC for 3 hours. The stereochemistry effect of reactants is evaluated by computer modelling using PM3 semiempirical methods. The mass spectrum of catalytic hydrogenation product from those compounds shows a molecular ion at m/z 164, which proves the existence of 2 -methoxy-4-propylphenol. The eugenol gives the highest conversion (99%), followed by cis-isoeugenol (81%) and trans-isoeugenol (67%). It was found that there is a correlation between the stereochemistry of those compounds and catalytic reactivity.