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primary alcohol + HX (Sn2 rxn)
secondary or tertiary alcohol + HX (Sn1)
hydroxyl group to better LG
PBr3, pyridine (inversion)
SOCl2, pyridine (inversion)
MsCl, pyridine (retention)
TsCl, pyridine (retention)
hydroxyl to better LG
alcohol + NaH or NaNH2 + alkyl halide
williamson ether synthesis (alcohol to ether)
alcohol + [H+]
ether synthesis via an acid catalyst (creates ONLY symmetrical ethers)
ether + HBr or HI
acid cleavage of ethers (cleaved into alkyl halides)
epoxide + grignard or alcohols or water
epoxide opening (basic conditions, attack less substituted side)
epoxide + hydrohalic acids or acids/ water w/ acid catalyst
epoxide opening (acidic conditions, attack more substituted sides)