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Alkene Hydrogenation
H2 + Pd/C or Pt0
Alkene Hydrohalogenation
HCl, HBr, HI
Alkene Hydration Carbocation
H2SO4 + H2O
Alkene Isomerization
H2SO4
Alkene Halogenation
Cl2, Br2
Alkene Halohydrin Synthesis
Br2, Cl2 and HOH
Alkene Oxymercuration-Reduction
Hg(OAc)2, HOH
NaBH4, NaOH
Alkene Hydroboration-Oxidation
BH3
H2O2, NaOH
Alkene Epoxidation
mCPBA, peracetic acid, or trifluoroperacetic acid
Alkene Syn-Dihydroxylation
OsO4 (stoich)
H2S or Zn metal
Alkene Ozonolysis (Reductive Workup)
O3
S(CH3)2
Alkene Ozonolysis (Oxidative Workup)
O3
H2O2, H2O
Alkyne Reduction
H2 and Pd/C or Pt0
Alkyne Partial Reduction Cis Alkene
H2 and Pd/CaCO3, Pb(OAc)2, and Quinoline
Lindlar’s Catalyst
Pd/CaCO3, Pb(OAc)2, and Quinoline
Alkyne Partial Reduction Trans Alkene
Na metal (radical), NH3 (l)
Alkyne Hydrohalogenation
HCl, HBr
Alkyne Halogenation
Br2, Cl2
Alkyne Hydration + Carbonyl Most Subbed
HgSO4, H2SO4 and H2O
Alkyne Hydration Hydroboration-Oxidation Carbonyl Least Subbed
(C6H11)2BH
H2O2, NaOH