SolutionsOxidation
1. Which acid is formed?
Give the organic product of: a) propylbenzene with hot KMnO4; b) 1-butanol with KMnO4; c) (E)-3-hexene with hot concentrated KMnO4; d) benzaldehyde with Ag2O.
- Benzoic acid: the chain is oxidized at the benzylic position and the other carbons are lost.
- Butanoic acid.
- Two molecules of propanoic acid, by cleavage of the double bond.
- Benzoic acid.
2. An alkylbenzene that resists
tert-Butylbenzene is not oxidized by KMnO4, whereas toluene gives benzoic acid. Why?
Oxidation starts at a benzylic hydrogen. tert-Butylbenzene has none (its benzylic carbon is quaternary), so the side chain is not attacked.