HBr -->
add more negative to more substituted carbon
H2O, H+ -->
OH goes on more substituted. Protonate, Cation Capture, Deprotonate
Br2 -->
added trans, cation formation, cation capture, mechanism forms a triangle
Br2, H2O -->
OH adds to more substituted. Cation capture, inversion, mechanism forms a triangle
CH3CO3H, H2O -->
adds OH OH trans, mechanism forms a triangle
H2SO4, Heat -->
removes OH, protonate, eliminate, deprotonate
Mechanisms that add OH
H2O H+, Hg(OAc)2 H2O NaBH4, BH3THF H2O2 NaOH
HBr, Peroxides -->
adds H and Br either cis or trans
Hg(OAc)2, H2O, NaBH4 -->
add OH markovnikov
BH3-THF, H2O2, NaOH -->
adds OH and H cis, antimarkovnikov
Hg(OAc)2, ROH, NaBH4 -->
adds OR markovnikov
H2, Pt
adds two H cis
PhCO3H -->
adds one O cis
OsO4, H2O2 -->
adds two OH cis