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Question
Propose structures for hydrocarbons that give the following products on oxidative cleavage by KMnO4 or O3:
Propose structures for hydrocarbons that give the following products on oxidative cleavage by KMnO4 or O3:
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Solution
The correct option is D
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:
The aldehyde and ketone groups at carbons 2 and 6 respectively should have come from ozonolysis
of the above product to the right of the retrosynthetic analysis arrow.
This compound and CO2 are courtesy of the oxidative cleavage of this terminal alkyne:
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:
The aldehyde and ketone groups at carbons 2 and 6 respectively should have come from ozonolysis
of the above product to the right of the retrosynthetic analysis arrow.
This compound and CO2 are courtesy of the oxidative cleavage of this terminal alkyne:
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