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hydrohalogenation
Mark
CCR possible
Addition of H and X (Cl,Br, or I)
Conditions: HCl, HBr, HI
hydration
Mark
Conditions: h2so4, h2o, h3o+
Addition of H and OH
hydroboration-oxidation
Anti-Mark
Syn, no CC
Conditions: BH3 - THF, H2O2, NaOH
hydrogenation
Syn
Addition of H and H
Conditions: H2/D2 & Pd, Pt, NI,
halogenation
Anti (inversion of stereochem)
Addition of X and X (Cl, Br)
Cyclic intermediate
Conditions: X2
hydroxyhalogenation
OH is on the more substituted position
Anti (inversion)
Cyclic Intermediate
Adds OH and X
Conditions: Br2, H2O
dihydroxylation - SYN
Syn
Conditions: OsO4, NMO
Adds OH and OH
dihydroxylation - ANTI
Anti
Attacks epoxide
Conditions: mCPBA, OH-, H2O
epoxidation
Syn
Forms epoxide
Conditions: mCPBA
ozonlysis
conditions: O3, DMS or Zn/H2O