|
Alkyne to cis-alkene |
|
H2, Ni2B |
| |
|
Alkyne to trans-alkene |
|
1) Li in NH3
2) NH4 Cl |
| |
|
Hydrohalogenation
(Br to an alkene) |
|
H-Br |
| |
|
Hydration
(OH to an alkene) |
|
H30+, H2O |
| |
|
Dihalogenation
(anti-Br addition) |
|
Br2 |
| |
|
Halohydrin Formation
(anti-OH+Br addition) |
|
Br2 in H2O |
| |
|
Markovinov OH addition
(no rearangement) |
|
1)Hg(OAc)2, HOR (C or H)
2) NaBH4, OH- |
| |
|
Anti Markovnikov OH addition |
|
1) BH3, THF
2) H2O2, OH- |
| |
|
syn- 2 OH addition |
|
1)OsO4
2) NaHSO3 |
| |
|
Carbon Triangle addition |
|
CH2I2, Zn (Cu) |
| |
|
Double Bond Cleavage |
|
1) O3
2) Zn, HOAc |
| |
|
Alkyl Halides from Alcohols |
|
PBr3 or SOCl2 |
| |
|
Cl Triangle |
|
CCl2- |
| |
|
Halogenation of Alkenes |
|
Br2 + heat or light |
| |
|
Anti-Markovnikov addition of HBr to Alkenes |
|
Peroxide + heat |
| |
|
Ethers from alcohols |
|
NaH |
| |
|
Epoxides from Alkenes |
|
mCPBA |
| |
|
Anti 1-2 Alcohols from Epoxidation |
|
Open epoxide with H2SO4 in H2O |
| |
|
Carboxylic Acid or Ester to Primary Alcohol |
|
1) Li AlH4, Et2O
2) H2O, H2SO4 |
| |
|
Ketone or Aldehyde to Primary Alcohol |
|
1)NaBH4
2) H2O |
| |
|
Primary Alchohol to Aldehyde |
|
PCC in CH2Cl2 |
| |
|
Primary Alcohol to Carboxylic Acid |
|
KMnO4 in OH-, H2O |
| |
|
Secondary Alcohol to Ketone |
|
H2CrO4 in acetone |
| |
|
Aldehyde to Secondary alc. |
|
Grignard |
| |
|
Ketone to Tertiary alc. |
|
Grignard |
| |
|
Ester to Tertiary alc. |
|
Two Grignards |
| |
|
Alkynides + Ketones or Aldehydes |
|
Secondary or Tertiary alc. |
| |
|
Gringard + Epoxide |
|
R group attacks less-substituted carbon atom in the ring |
| |
