Reagent List for Alkene Reactions

H2/Pd, Pt or Ni

Syn addition of hydrogen, concerted mechanism

Cl2 or Br2

Anti addition of halogen, goes through halonium ion intermediate

KMnO4, OH-

Syn addition of 2 OH groups, concerted mechanism

1. OsO4

2. NaHSO3

Syn addition of 2 OH groups, concerted mechanism

H3O+

Addition of H and OH, goes through a carbocation intermediate, follows Markovnikov's Rule, no specific stereochemistry observed

1. Hg(OAc)2

2. NaBH4

Addition of H and OH, goes through a mercurium ion intermediate, follows Markovnikov's Rule, no rearrangement or specific stereochemistry

1. BH3

2. H2O2, OH-

Syn addition of H and OH, non-Markovnikov Product is observed, syn addition

HBr or HCl

Addition of H and X, goes through a carbocation intermediate, follows Markovnikov's Rule, not stereospecific

HBr or HCl with peroxides

Addition of H and X, goes through a radical intermediate, non-Markovnikov addition, not stereospecific

Br2/H2O or Cl2/H2O

Anti addition of X and OH, goes through a halonium ion intermediate, no rearrangement, OH goes on most hindered carbon of double bond

1. O3

2. Zn, HOAc

Cuts the double bond and produces two carbonyl compounds

KMnO4(aq), H+

Cuts the double bond and produces two carboxylic acids

1. KMnO4, OH-

2. HIO4

1. Makes a syn addition of OH creating a diol

2. Cuts the diol into two carbonyl groups

RCO3H

epoxidation reaction using a peroxyacid (mCPBA)

1. RCO3H

2. H3O+

epoxidation reaction followed by a ring opening reaction to make a vicinal diol with anti configuration.

CH2I2 with Zn(Cu)

Simmons-Smith reaction forms a cyclopropyl ring