SolutionsOxidation of Alcohols

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1. Products

Give the oxidation product of each alcohol:

1-Butanol with PCC in CH₂Cl₂
1-Butanol with KMnO₄ in basic medium (and acidification)
2-Butanol with H₂CrO₄
2-Methyl-2-butanol with H₂CrO₄

Butanal.
Butanoic acid.
Butanone.
It is not oxidized: it is a tertiary alcohol.

2. Stopping at the aldehyde

Why is it hard to obtain aldehydes by oxidizing primary alcohols in water?

Because in water the aldehyde forms its hydrate, which is easily oxidized to the carboxylic acid. PCC, soluble in organic solvents, allows working without water.

3. Oxidation state of chromium

How does the oxidation state of chromium change when a secondary alcohol is oxidized with chromic acid?

It goes from +6 to +4: chromium is reduced while the carbon of the alcohol is oxidized from 0 to +2.

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