CHM 203 Reagents Flashcards
Primary Alcohol Oxidation
Make Aldehyde from Alcohol
PCC/DCM
Primary Alcohol Oxidation
Make Carboxylic Acid from Alcohol
H2CrO4/H2SO4
Secondary Alcohol Oxidation
Make Ketone from Alcohol
PCC/DCM
Alcohol Halogenation
Remove OH, Add Halogen
PBr3 or SOCl2(tosyl chloride)/Pyridine(py)
Free Radical Halogenation
- Br2/CCl4, hv
- MgO, Et2O
- Ketone OR Epoxide
- H3O+/H2O
Diol Synthesis (trans)
NaOH/H2O
starting from a cyclic epoxide
Diol Synthesis (cis)
KMnO4/NaOH, H2O
starting from a double bond on a hexane
Diol Synthesis (cis)
OsO4/H2O2
starting from a double bond on a hexane
Alkene Reduction
H2, Pd/C or ClRh(PPh3)3
Cycloproponation (H)
CH2I2/Zn, Cu
starting from double bond on hexane
Cycloproponation (Cl)
HCCl3 in HOBut/tOBut
starting from alkene
Cycloproponation (Br)
CHBr3 in HOBut/tOBut
starting from alkene
Hydration of Alkene
Markovnikov
- Hg(OAc)2
2. NaBH4/NaOH
Hydration of Alkene
Anti-Markovnikov
- “BH3”/THF
2. H2O2/NaOH
Epoxidation
starting from double bond on hexane
- Br2 or Cl2/H2O
2. NaOH
Epoxidation
syn, starting from alkene
mCPBA/DCM
Ozonolysis
- O3/DCM
2. (CH3)2S
Halogenation of Alkynes
adding H/X
H-X
Halogenation of Alkynes
adding H/X or Base/X
H-X/H-Base
Halogenation of Alkynes
adding X/X
X2/DCM
Synthesis of Alkyne Carbanion
NaNH2/NH3
Ketone Synthesis
HgSO4/H2SO4
Aldehyde Synthesis
- R2BH/THF
2. H2O2/NaOH
Alkyne Synthesis
terminal
- NaNH2/NH3
2. H3O+
Alkyne Synthesis
substituted
- HOBut/KOBut
2. H3O+
Alkyne Hydrogenation
trans
- Na, NH3
2. H3O+
Alkyne Hydrogenation
cis
H2, Pd/Pb/C (Lindler’s)
