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H2SO4, heat
E1
rearrangement possible
turns to alkene
SOCl2/pyridine or PBr3
forms alkyl halide
via Sn2, OH to X
PCC or DMP
stops at aldehyde
Primary OH turns to aldehyde
Secondary OH turns to ketone
Jones (CrO3/H2SO4), KMnO4
COOH formed