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H₂SO₄ / H₂O
acid-catalyzed hydration of alkenes
Alkene → alcohol (Markovnikov)?
BH₃ then H₂O₂ / OH⁻
hydroboration-oxidation of alkenes
Alkene → alcohol (anti-Markovnikov)?
HBr / HCl / HI
hydrohalogenation of alkenes
Alkene → alkyl halide (Markovnikov)?
HBr / ROOR
radical anti-Markovnikov addition of HBr
Alkene → alkyl halide (anti-Markovnikov)?
Br₂ / CCl₄
halogenation of alkenes
Alkene → vicinal dihalide?
Br₂ / H₂O
halohydrin formation from alkenes
Alkene → halohydrin?
mCPBA
epoxidation of alkenes with mCPBA
Alkene → epoxide?
less substituted carbon
epoxide ring opening basic conditions
Epoxide + OH⁻ attacks where?
more substituted carbon
acid-catalyzed epoxide opening
Epoxide + H⁺ attacks where?
ring strain
Why are epoxides reactive?
mCPBA then OH⁻ / H₂O
epoxide hydrolysis
Alkene → epoxide → diol?