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[thomasjr (touch)]

Oxidation reaction of alcohols

1 degree alcohols with PCC  =====> aldehydes

1 degree alcohols with CrO3 (H2SO4/H2O) =====> carboxylic acids

2 degree alcohols with PCC or CrO3 =====> ketones

Oxidation reactions of aldehydes

with CrO3 Na2Cr2O7 K2Cr2O7 KMnO4 =====>carboxylic acids

with Ag2O NH4OH =====> carboxylic acids

----------------------------
Reduction reactions

Aldehydes and ketones

NaBH4/CH3OH(less strong) or LiAlH4->H2O or H2/Pd/C =====> alcohols

αβunsaturated aldehydes and ketones

1. with NaBH4/CH3OH =====> only C=O bond is reduced

2. with H2(1 equiv)/Pd/C =====> only C=C bond is reduced

3. with H2(excess)/Pd/C =====> both double bonds are reduced

Acid Chlorides

1.with LiAlH4->H2O(strong reductant) =====> 1 degree alcohols

2.with LiAlH[OC(CH3)3]3(weak reductant) =====> aldehydes(no reactions with C=O)

Esters

1.with LiAlH4->H2O =====> 1 degree alcohols

2.with DIBAL-H->H2O(weak reductant) =====> aldehydes(reaction stopped at this stage)

Carboxylic acids

with LiAlH4->H2O =====> alcohols

Amides

with LiAlH4->H2O =====> amines


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