Alkene Reagents Flashcards
Hydrohalogenation
- H & X are added across a double bond
- Markovnikov
Acid-catalyzed hydration
- H & OH are added across a double bond
- In presence of steric hindered acid
- C+ rearrangements
- Syn + Anti addition
Oxymercuration-Demercuration
- H & OH are added across a double bond
- Markovnikov
- Anti-addition
Hydroboration-Oxidation
- H & OH are added across a double bond
- Anti-Markovnikov
- Syn-addition
Catalytic Hydrogenation
- H & H are added across a double bond
- syn addition
* Pt, Pd, Ni
Halogenation
- X & X are added across a double bond
- Anti-addition
Halohydrin formation
X & OH are added across a double bond
- OH group is generally installed at the more substituted position
- Anti-addition
1.) RCO3H or MCPBA or MMPP
2.) H3O+ or H2O + OH-
Anti Dihydroxylation
- OH & OH are added across a double bond
- Anti-addition
Unsymmetrical Epoxides
1.) RCO3H or MCPBA or MMPP
2.) Nuc-
3.) H2O
Unsymmetrical Epoxides
- Nuc & OH are added across a double bond
- Nuc attacks less subs. C, then O- gets protonated
- Anti-addition
Unsymmetrical Epoxides
1.) RCO3H or MCPBA or MMPP
2.) H3O+ or H2SO4 (or H-X as acid+nuc)
3.) Weak Nuc
Unsymmetrical Epoxides
- Nuc & OH are added across a double bond
- O gets protonated first, then Nuc attacks more subs. C
- Anti-addition
Syn Dihydroxylation
- OH & OH are added across a double bond
- Syn-addition
Ozonolysis
C=C bond is completely split apart to form two C=O bonds
Hydrohalogenation
- H & X are added across a double bond
- Anti-Markovnikov
Oxidation of benzylic position
- must have a H
- can use KMnO4/H3O+ Heat
Free radical bromination of benzylic position
Hydrogenation of benzene
- must be high heat & high pressure
Hydrogenation of allylic position
- vinyl group is selective
