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alkane to haloalkane
X2, UV light
alkene to alkane
H2, nickel catalyst, 150 degrees
alkene to dihaloalkane
X2, 20 degrees
alkene to haloalkane
HX, 20 degrees
haloalkane to alcohol
warm NaOH or KOH, H2O, reflux
alcohol to haloalkane
NaX, H2SO4, 20 degrees
alcohol to aldehyde
acidified potassium dichromate, distil