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Question

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:


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