HX
——>
Hydrohalogenation
- Halogen is added to more substituted Carbon on the double bond
HBr
———>
ROOR
Radical Addition
- Anti Markovnikov addition of H and Br
- Occurs in presence of Peroxide ROOR
H20
—————>
Catalytic Acid
Acid Catalyzed Hydration
- Markovnikov addition of H and OH
- Converts Alkene to an Alcohol
- Carbocation Rearrangements are possible
1) Hg(OAc)2, H2O, THF
———————————>
2) NaBH4
Oxymercuration - Demercuration
- Markovnikov addition of H and OH
- if 1 chiral center is formed, then there are 2 products
- if 2 chiral centers are formed, then there are 4 products
- NO CARBOCATION REARRANGEMENTS
1) BH3, THF
——————>
2) H2O2, NaOH
Hydroboration Oxidation
- Anti Markovnikov addition of H and OH
- Stereospecific SYN addition
- No Carbocation Rearrangements
Br2 or Cl2
—————>
CCl4
Dihalogenation
- Anti Addition of Br2 or Cl2
- Stereospecific
- Involves formation of Halonium Ion Intermediate
- Practice Mechanism!
Br2 or Cl2
—————>
H2O
Halohydrin Formation
- Anti Addition of Br/Cl and an OH group
- Involves formation of Halonium Intermediate, followed by water attacking most substituted ring carbon
- Stereospecific
RCO3H
————>
mCPBA
Epoxidation
- Results in an Epoxide
- If product is Chiral, both enantiomers will be formed
1) RCO3H, mCPBA
—————————>
2) H3O+
Anti Dihydroxylation
- Anti Addition of two OH
- Alkene is reacted with Peroxyacid such as RCO3H or mCPBA
- the epoxide that forms is reacted with aqueous acid (acid and H2O) or aqueous base (NaOH and H2O)
- Practice Mechanism!
1) OsO4 1) KMnO4, NaOH
————> ————————>
2) H2O2 Cold
SYN Dihydroxylation
- the addition of two OH on an Alkene in SYN fashion
- product will include its associated enantiomer
Reductive Workup
1) O3
———————————>
2) DMS or Zn, HOAc
Oznolysis Reductive Workup
- cleaves carbon-carbon double bond to produce two carbonyl containing compounds
- if an Alkene carbon is bonded to a hydrogen, a reductive workup converts the Alkene carbon to an ALDEHYDE
- if an Alkene carbon is bonded to two carbon atoms, a keytone is produced regardless of workup used
Oxidative Workup
1) O3
————>
2) H2O2
Oznolysis Oxidative Workup
- cleaves carbon-carbon double bond to produce two carbonyl containing compounds
- if an Alkene carbon is bonded to a hydrogen, a oxidative workup converts the Alkene carbon to a carboxylic acid
- if an Alkene carbon is bonded to two carbon atoms, a keytone is produced regardless of workup used
H2
—————>
Pd, Pd/C, Pt
Catalytic Hydrogenation
- Reduces an Alkene to an Alkane
- Alkene will react with Hydrogen atoms on surface of a metal catalyst
- Either side of the Alkene can interact with the metal catalyst in a SYN fashion
- Both Enantiomers are formed
