Oxidation and reduction

alkene to alkane

Pd/C, H2

syn addition

aldehyde to alcohol

Pd/C, H2

ketone to alcohol

Pd/C, H2

alkyne to alkene syn addition

H2, lindlar’s catalyst

alkyne to alkene anti addition

Na+, NH3

epoxide to alcohol

LiALH4, H2O

least substituted side (Sn2)

C-X, to C-H

LiAlH4

syn addition, (Sn2)

tosylates to C-H

LiAlH4

syn addition, (Sn2)

alkene to epoxide

MCPBA, syn addition

dihydroxylation alkene to 2Oh syn diol

1) OSO4, 2) NaHSO3, H2O

dihydroxylation alkene to 2 OH anti diol

1) MCPBA, 2) KOH

oxidative cleavage of alkenes

1) O3, 2) Me2S or Zn+H2O

oxidative cleavage of alkynes

1) O3, 2) H2O

oxidation of secondary alcohol

PCC

ketones

oxidation of primary alcohol (PCC)

PCC

aldehyde

oxidation of primary alcohol (Jones)

Jones (CrO3, H2SO4, H2O)

carboxylic acid

oxidation of aldehyde to carboxylic acid

Jones (CrO3, H2SO4, H2O)

carboxylic acid

PCC

pyridine + CrO3Cl