H2, Pd/C
Alkane
H2, Lindlar Cat.
Cis alkene
NaNH2, NH3 (l)
Trans alkene
***DO NOT USE ON TERMINAL ALKYNES
H3O+
Alcohol
Br2, H2O
Halohydrin
Br2, ROH
Haloether
Hg(OAc)2, H2O, NaBH4
Alcohol without alkyl shift
Hg(OAc)2, ROH, NaBH4
Ether without alkyl shift
H+ cat., CH3OH
Ether (alkyl shift)
BH3, THF, H2O2, NaOH
Alcohol (Anti-Markovnikov, syn)
Hg2+, H3O+
Ketone
R2BH, H2O2, NaOH
Aldehyde (Anti-Markovnikov)
O3, Me2S
Ketone(s) and/or aldehyde(s)
O3, H2O2
Ketone(s) and/or carboxylic acid(s)
HBr, ROOR
Anti-Markovnikov addition of Br
NaN3, H2, Pd/C
SN2
Alkyl halide to Alkane-NH2