Alkene Reactions

hydrohalogenation conditions

H-X

hydrohalogenation adds

H, X

hydrohalogenation syn or anti?

both

hydrohalogenation regioselectivity

markovnikov

hydrohalogenation rearrangement?

yes

acidic hydration conditions

H2SO4, H2O

acidic hydration adds

H, OH

acidic hydration syn or anti?

both

acidic hydration regioselectivity

markovnikov

adicid hydration rearrangements?

yes

oxymercuration-demercuration conditions

Hg(OAC)2, H20, NaBH4

oxymercuration-demercuration adds

H, OH

oxymercuration-demercuration syn or anti?

anti

oxymercuration-demercuration regioselectivity

markovnikov

oxymercuration-demercuration rearrangement?

no

hydroboranation-oxidation conditions

BH3, H2O2, NaOH, H2O

hydroboranation-oxidation adds

H, OH

hydroboranation-oxidation syn or anti?

syn

hydroboranation-oxidation regioselectivity

anti-markovnikov

hydroboranation-oxidation rearrangements?

no

dihydroxylation conditions

OsO4, NaHSO3, H2O

dihydroxylation adds

OH, OH

dihydroxylation syn or anti?

syn

dihydroxylation rearrangement?

no

hydrogenation

H2, Pd/C

hydrogenation adds

H, H

hydrogenation syn or anti?

syn

hydrogenation rearrangement?

no

halogenation conditions

X2 (not F2)

halogenation adds

X, X

halogenation syn or anti?

anti

halogenation rearrangement?

no

halohydrin conditions

X2, H2O or ROH

halohydrin adds

X, OR/OH

halohydrin syn or anti?

anti

halohydrin regioselectivity

markovnikov

halohydrin rearrangement

no

epoxide + ring-opening conditions

MCPBA, strong nuc, H3O+

epoxide + ring-opening adds

OH, nuc (R/H)

epoxide + ring-opening syn or anti?

anti

epoxide + ring-opening regioselectivity

markovnikov

epoxide + ring-opening rearrangement?

no