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Addition of HX
H-Br
(Mark and No Stereo Specificity)
Addition of HX - Free Radical Addition
H-Br and ROOR
(Anti Mark and No Stereo Specificity)
Direct Hydration
H3O+ and dil H2SO4
(Mark, No Stereo Specificity, Shifts (H or CH3)
Oxymercuration - Demercuration
1) HgOac, H2O or CH3OH
2)NaBH4
(Mark and Anti addition)
Hydroboration
1) BH3, THF
2) H202, OH-
(Antimark and Syn addition)
Diazomethane
1) NNCH2
(Cyclopropane Addition)
Simmons Smith
1) CH2I2 with Zn,CuCl2
(Cyclopropane Addition)
Alpha Elimination
1) CHCl3 with KOH, H2O
(Carbene Formation)
Addition of Halogens
Br2, Cl2, and sometimes I2 in CCl4
(Mark and anti addition)
Formation of Halohydrin
Br2 and Cl2 in H2O
(Mark and anti addition)