Propose structures for hydrocarbons that give the following products on oxidative cleavage by KMnO4 or O3:
A
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B
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C
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D
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Solution
The correct option is B Non-terminal alkynes, on oxidative cleavage yield carboxylic acids. Lack of symmetry around the triple bond would yield a mixture of acids. Terminal alkynes - on a similar reaction yield a carboxylic acid and CO2:
So we can surmise one part - the keto acid and CO2 as coming from:
The compound on the right has a keto group and acetaldehyde together could be attributed retrosynthetically to: