addition reaction reagents

ch. 9 - ch. 8

H-X (with ROOR/H2O2 sometimes)

hydrohalogenation of alkenes

H-X or xs H-X (with ROOR/H2O2 sometimes)

hydrohalogenation of alkynes

H3O+ or H2SO4 with H2O

acid-catalyzed hydration of alkenes

H2SO4, H2O and HgSO4

hydration of alkynes (mercuric ion induces Nu attack(tautomerization occurs to form ketone))

BH3, THF and H2O2, NaOH

hydroboration-oxidation of alkenes and alkynes (alkynes form ketones)

Hg(OAc)2, H2O with NaBH4

oxymercuration-demercuration of alkenes

X2 with Pd, Pt, or Ni

halogenation of alkenes

one equivalent X2 or xs X2 with CCl4

halogenation of alkynes

O3 with DMS or ZnH2O

ozonolysis of alkenes

O3 with H2O

ozonolysis of alkynes

RCO3H with H3O+

anti dihydroxylation of alkenes

OsO4 or KMnO4

syn dihydroxylation of alkenes

X2 with H2O

halohydrin formation of alkenes

NaNH2 with functional group

alkylation of alkynes

H2 with Pd, Pt, or Ni

metal-catalyzed reduction of alkynes

H2 with Lindlar’s cat or Ni2B

poisoned catalyst reduction of alkynes

H2 with Na (metal), NH3 (l)

dissolving metal reduction of alkynes