oxidative cleavage

Question

Hot KMnO4 oxidation of terminal alkene yields carboxylic acid and:

RankGuru · Accepted Answer

1. **Reagent Power**: Hot, acidified or alkaline $KMnO_4$ is an extremely vigorous oxidant that causes oxidative cleavage of $C=C$ bonds.
2. **Internal Double Bonds**: Cleave to form two carboxylic acids (or ketones depending on substitution).
3. **Terminal Double Bonds**: Specifically, the $=CH_2$ group is first oxidized to formaldehyde ($HCHO$) or formic acid ($HCOOH$).
4. **Over-oxidation**: Formic acid is extremely susceptible to further oxidation and is promptly converted to **Carbon dioxide ($CO_2$)** and water.
5. **Summary**: A terminal alkene $R-CH=CH_2$ will yield $R-COOH$ and $CO_2$.

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oxidative cleavage

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