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R-OH, NaOH, heat, conc. H2SO4, heat, Na, HCl / PCl3 / PCl5 / SOCl2,…
R-OH
PCC / CH2Cl2
secondary alcohol - ketone
tertiary alcohol - no reaction
primary alcohol - aldehyde
CH3MgBr
i) ether
ii) H2O+
alcohol from grignard
nucleophilic addition
alkene
dehydration
alkyl halide
nucleophilic substitution
alkene
hydration
R-O -Na+
sodium alkoxide
ROOR'
esterification
R-X
conversion to haloalkene
NaOH, heat
conc. H2SO4, heat
Na
HCl / PCl3 / PCl5 / SOCl2
aldehyde/ketone