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Oxidative cleavage of alkenes to ketones/carboxylic acids using KMnO4

Description: Alkenes treated with KMnO4 are cleaved into carbonyl compounds. The type of carbonyl compound depends on the substitution pattern of the alkene.

Notes: The reaction is generally run with aqueous acid and heat.

Examples:

Notes: Note that all C–H bonds attached to alkenes are oxidized to C–OH bonds, but alkene carbons with only carbons attached become ketones. Note that the last example is a cyclic alkene that goes to a linear product.

Mechanism: The detailed mechanism for this reaction is generally not considered important for the purposes of Org 1 / Org 2, although the first step is dihydroxylation of the alkene.