alcohol --> ether (using primary/unhindered alkyl halide)
Williamson ether synthesis [SN2]
thiol --> sulfide (using sulfonate ester)
williamson ether synthesis [SN2] - w/ sulfur
alkene --> ether (alcohol solvent)
primary alcohol --> symmetrical ether
alcohol dehydration, harsh conditions [SN2]
tertiary alcohol --> unsymmetrical ether (primary alcohol solvent)
alcohol dehydration, mild conditions; make sure solvent does not form carbocation too [SN1]
alkene --> unsymmetrical ether
alkene addition that produces the same carbocation intermediate as alcohol dehydration
alkene --> epoxide (syn addition)
peroxycarboxylic acid (mCPBA, MMPP) [similar to bromonium ion]
halohydrin (O, X are anti) --> epoxide
cyclization of halohydrin ("intramolecular williamson ether") [intra- SN2]
epoxide --> glycol (inversion)
acid-catalyzed epoxide ring opening
epoxid --> glycol (syn)
oxidation with OsO4 [similar to ozonolysis]
two-carbon chain extension
add HBr to alcohol; create Grignard reagant; attack epoxide
sulfonate esters, alkyl halides
primary alcohol --> carboxylic acid
oxidation with KMnO4 (second step = strong acid)
OH --> Br
HBr and H2SO4 acid; use PBr3 to minimize rearrangements
making Grignard reagant
add Mg to alkyl bromide; must use ether solvent (ex. THF)
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