Organic Chemistry: Addition Reactions

Hydrohalogenation

Regioselectivity: Markovnikov; anti-Markovnikov in the presence of peroxides R-OO-R

Stereoselectivity: N/A; Enantiomers in equal amounts; racemic

Reagents: HBr, HCl, HI

Details: --

Acid-Catalyzed Hydration

Regioselectivity: Markovnikov

Stereoselectivity: N/A; Enantiomers in equal amounts

Reagents: H3O+, H2O/H2SO4,

Details: Carbocation Rearrangement can occur; Only efficient when rearrangements cannot occur;

Oxymercuration-Demercuration

Regioselectivity: Markovnikov

Stereoselectivity: syn

Reagents: 1. Hg(OAc)2, H2O; 2. NaBH4

Details: No Rearrangement

Hydroboration-Oxidation

Regioselectivity: Anti-Markovnikov

Stereoselectivity: Syn Addition

Reagents: 1. BH3*THF; 2. H2O2, NaOH

Details: Concerted process; Addition of water across a pi bond

Halogenation

Regioselectivity: N/A

Stereoselectivity: Anti Addition

Reagents: Only Br2 and Cl2

Details: --

Halohydrin

Regioselectivity: N/A

Stereoselectivity: Anti Addition

Reagents: Br2 or Cl2 over H20

Details: Hydroxide is installed on the more substituted side of the double bond

Anti-Dihydroxylation

Regioselectivity: N/A

Stereoselectivity: Anti Addition

Reagents: 1. MCPBA; 2. H3O+ or H2SO4

Details: Involves formation of an epoxide; Can involve OH- or OMe- or OEt-

Syn-Dihydroxylation

Regioselectivity: N/A

Stereoselectivity: Syn Addition

Reagents: OsO4/NMO, NaHSO3+H2O; KMnO4,NaOH/cold;

Details:--

Oxidative Cleavage

Regioselectivity: N/A

Stereoselectivity: N/A

Reagents: 1. O3; 2. DMS

Details:Mainly oznolysis

Catalytic Hydrogenation

Regioselectivity: N/A

Stereoselectivity: Syn Addition

Reagents: H2 over a metal

Details:Pt, Pd, and Ni are heterogeneous catalysts; Wilkinson's catalyst is homogeneous