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H20, H+, H3O

1) Hg2, H2O / 2) NaBH4

1) BH3 / 2) H2O2, NaOH

Br2, H2O

Br2

O3

H2, Lindlar (Pd, Ni)

OsO4

H-X (X = Br, Cl)

H2, Lindlar (Pd, Ni)

1) (sia)2 BH / 2) NaOH, H2O2
(sia)2 BH used for terminal alkynes. BH3 for internal alkynes.

1) Br2 / 2) 3 (-)NH2 / 3) H2O

(-)NH2 or NaH or LDA

R - CH2 Br

(on an alkyne) H20, H2SO4 or H30
Chlorine free radical reaction

Bromine free radical reaction
