Alkene Addition Reactions

Hydrohalogenation without ROOR

Reagents: HX (Cl, Br, I)

What adds: H + X

Regio: mark

Stereo: all

Extra Info: carbocation rearrangement

Hydrohalogenation with ROOR

Reagents: HBr, ROOR

What adds: H + Br

Regio: anti mark

Stereo: all

Extra Info: none

Acid-Catalyzed Hydration

Reagents: H₃O⁺ (or H₂O + H₂SO₄)

What adds: H + OH

Regio: mark

Stereo: all

Extra Info: carbocation rearrangement

Oxymercuration-Demercuration

Reagents: 1) Hg(OAc)₂, H₂O
2) NaBH₄

What adds: H + OH

Regio: mark

Stereo: anti

Extra Info: no rearrangement

Hydroboration-Oxidation

Reagents: 1) BH₃·THF
2) H₂O₂, NaOH

What adds: H + OH

Regio: anti mark

Stereo: syn

Extra Info: BH₂ replaced by OH

Hydeogenation

Reagents: H₂, Pd (Pt/Ni also)

What adds: H + H

Regio: none

Stereo: syn

Extra Info: none

Halogenation

Reagents: Br₂ (or Cl₂), CHCl₃

What adds: X + X

Regio: none

Stereo: anti

Extra Info: bromium ion intermediate

Halohydrin

Reagents: Br₂ + H₂O

What adds: Br + OH

Regio: OH more sub side

Stereo: anti

Extra Info: water = nucleophile

Anti-Dihydroxylation

Reagents: 1) mCPBA
                  2) H₃O⁺

What adds: OH + OH

Regio: none

Stereo: anti

Extra Info: epoxide

Syn-Dihydroxylation

Reagents: OsO₄ + NaHSO₃ or cold dilute KMnO₄

What adds: OH + OH

Regio: none

Stereo: syn

Extra Info: cyclic osmate ester

Ozonolysis

Reagents: O₃ + DMS (or Zn/H₂O)

What adds: none

Regio: none

Stereo: none

Extra Info: forms aldehyde/ ketone