addition rxns orgo 1

Hydrogenation

Pd/C or Pt

stereospecific syn addition

electrophilic addition

H-X

racemic mixture

markovnikov addition of H-OH

catalytic h2SO4 or other strong acid

H20

racemic mixture

markovnikov selectivity

Addition of X2

CCl4 (or other nonpolar aprotic solvent)

stereospecific anti addition

markovnikov addition of X-OH (hydrohalogenation)

X2

h2o or other polar protic solvent

regiospecific markovnikov selection

stereospecific anti addition

selective addition of H-OH oxymercuration-demurcuration

1) Hg(OAc)2 , H2O

2) NaBH4, H2O, NaOH

regioselective markovnikov

stereospecific anti addition

anti-markovnikov addition of H-OH Hydroboration-oxidation

1) BH3 , THF solvent

2) H2O2, NaOH

regioselective anti-markovnikov

stereospecific syn addition

epoxidation

racemic

mCPBA

single enantiomer epoxidation

jacobsens catalyst

NaOCl

open epoxide anti-diol synthesis

catalytic H2SO4

H2O (or any proton donator)

stereospecific anti addition

dihydroxylation syn diol synthesis

catalytic OsO4

H2O2

stereospecific syn addition

reductive ozonolysis

O3

cold temo

Me2S. or NaHSO4

Oxidative Ozonoloysis

O3

cold temps

H2O2

creates carboxylic acid

anti- markovnikov addition of H-Br

HBr

ROOR

Racemic