Organic Chemistry Alkene Reactions

Addition of HX

Reagents: HCl, HBr, HI

Follows Markovnikov

Free Radical Addition of HBr

Reagents: HBr with a peroxide (H2O2/R-O-O-R)

Anti-Markovnikov

Hydration

Reagents: H+/H2O, H3O, dilute H2SO4, dilute H2PO4, 50% H2SO4

Markovnikov addition

Rearrangements possible through carbocation

Oxymercuration - Demercuration

Reagents: Hg(OAc)2/H2O & NaBH4 (reducer)

Markovnikov addition

No rearrangement

Anti-addition (two things add to opp. sides of double bond)

Hydroboration

Reagents: BH3 . THF & peroxide/NaOH (oxidizer)

Anti-Markovnikov

Syn addition

No rearrangement

Halogenation

Reagents: Cl2, Br2, sometimes I2

Anti addition

Halohydrin

Reagents: Cl2, Br2, and I2 in (and) H2O

Markovnikov

Anti-addition

Hydrogenation

Reagents: H2 and catalyst (Pt, Pd, Ni)

Syn addition

Addition of Carbenes: CH2N2

Addition of Carbenes: Simmons-Smith

Reagents: CH2I2 and Zn, CuCl

Addition of Carbenes: Alpha Elimination

Reagents: CHCl3, CHBr3, base

Epoxidation

Reagents: MCPBA

Opening of Epoxide Ring (H2O)

Reagents: H2O, H+

Opening of Epoxide Ring (Str. nucleophile)

Reagents: CH3CO3H & H+/CH3OH or CH3CO3H/CH3SH

Syn Diol (OsO4)

Reagents: OsO4 & H2O2/ROOR or KMnO4

Oxidative Cleavage with KMnO4

Reagents: KMnO4

Ozonolysis

Reagents: O3 & (CH3)2S

Gentler than KMnO4, keeps aldehyde