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hydrohalogenation
H,X
favors mark
racemic mixture
H-X
hydrobromination
H-Br
favors anti-mark
racemic mixture
Hydration
H,OH
favors mark
racemic
H2SO4 dilute
Hydroboration Oxidation
BH3 THF
H2O2, NaOH
syn addition
favors anti mark
Halogenation
X,X
makes two chiral centers
Hydroxyhalogenation
OH,X
X2, H2O
Hydrogenation
H2
typically mark
syn addition
syn-dihydroxylation
catalytic OsO4
H2O
syn addition
anti-dihydroxylation
mCPBA, H2O
anti addition
ozonolysis
O3,DMS
breaks pi bond and replaces w/O