R−CH=CH−R+H2→Ni,80∘CR−CH2−CH2−R\mathrm{R}-\mathrm{CH}=\mathrm{CH}-\mathrm{R}+\mathrm{H}_{2} \xrightarrow{\mathrm{Ni}, 80^{\circ} \mathrm{C}} \mathrm{R}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{R}R−CH=CH−R+H2Ni,80∘CR−CH2−CH2−R
CH2=CH2+[O]+H2O→HCl→KMnO4HOCH2−CH2OH\mathrm{CH}_{2}=\mathrm{CH}_{2}+[\mathrm{O}]+\mathrm{H}_{2} \mathrm{O} \xrightarrow[\mathrm{HCl}]{\stackrel{\mathrm{KMnO}_{4}}{\rightarrow}} \mathrm{HOCH}_{2}-\mathrm{CH}_{2} \mathrm{OH}CH2=CH2+[O]+H2O→KMnO4HClHOCH2−CH2OH
2R−C≡C−H+2Na(s)⟶NaOH2R−C≡Na(s)+H2( g)2 \mathrm{R}-\mathrm{C} \equiv \mathrm{C}-\mathrm{H}+2 \mathrm{Na}(\mathrm{s}) \stackrel{\mathrm{NaOH}}{\longrightarrow} 2 \mathrm{R}-\mathrm{C} \equiv \mathrm{Na}(\mathrm{s})+\mathrm{H}_{2}(\mathrm{~g})2R−C≡C−H+2Na(s)⟶NaOH2R−C≡Na(s)+H2( g)
CH3CH2CH2OH+[O] K2Cr2O7 dilute H2SO4CH3CH2CHO+H2O\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}+[\mathrm{O}] \underset{\text { dilute } \mathrm{H}_{2} \mathrm{SO}_{4}}{\mathrm{~K}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7}} \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CHO}+\mathrm{H}_{2} \mathrm{O}CH3CH2CH2OH+[O] dilute H2SO4 K2Cr2O7CH3CH2CHO+H2O
