OCHEM Exam 3 reactions =

Hydrogenation

H2 (plus metal catalyst), stereospecific (syn-addition of H)

Markovnikov Addition: Electrophilic addition

alkene reacts with H-X producing racemic mixture, regioselective (markovnikov), NOT stereoselective (C+ int), racemic mixture

Markovnikov Addition (H2O)

cat. H2SO4, TsOH, with H2O as nucleophile. regioselective (markovnikov) but not stereoselective

Markovnikov addition of X2 (X=Cl, Br, I)

X2 electrophile, Non-polar aprotic solvent (CCl4), regioselective (markovnikov), stereospecific (anti-addition)

markovnikov addition: Hydrohalogenation

X2 (X=Cl, Br, I), polar protic solvent, regioselective (markovnikov), stereospecific (anti-addition)

Markovnikov addition: Oxymercuration-demercuration

1) Hg(OAc)2, H2O and 2)NaBH4, H2O, NaOH. Regioselective (markovnikov) and stereospecific (anti-addition)

Anti-Markovnikov

addition of nucleophile to less substitued carbon

Markovnikov

Addition of nucleophile to more susbtituted carbon

ANTI-markovnikov: Hydroboronation Oxidation

1) BH3, THF 2)H2O2, NaOH, regioselective (anti-markovnikiv), stereospecific (syn addition, to same side)

Epoxidation

mCPBA, not enatiomer selective

Expoxidation (single enantimer)

Jacobsens Catalyst (Chiral) gives the O

Diol Synthesis (