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alcohol + Na/THF + X-CH3
ether (alcohol)
alkene + alcohol + Hg(oAc)2 + NaBH4/NaOH
ether (alkene)
2x primary alcohol + H2SO4
ether (2x primary alcohol)
tertiary alcohol + EtOH + H2SO4
ether (tertiary alc)
alkene + mCPBA/benzene
epoxide
alkene + Br/H2O + base/NaOH
epoxide
ether + strong acid
cleavage of ethers
epoxide + oEt/HoEt
opens epoxide
OH on more substituted
oET on less substituted
epoxide + CH3OH/H2SO4
opens epoxide
OH on less substituted
oET on more substituted
ethylene oxide (ch2-o-ch2) + gringnard reagent + ether,heat/H3O+
opens epoxide
epoxide + h2o/catH+
trans-glycol
alkene + OsO4/H2O
glycol
glycol + H5IO6
cleavage of glycols