Propose structures for hydrocarbons that give the following products on oxidative cleavage by $K M n O_{4}$ or $O_{3}$ :

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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 $C O_{2}$ :

So we can surmise one part - the keto acid and $C O_{2}$ as coming from:

The compound on the right has a keto group and acetaldehyde together could be attributed
retrosynthetically to:

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Similar questions

Q. Propose structures for hydrocarbons that give the following products on oxidative cleavage by

K M n O_{4}

O_{3}

Propose structures for hydrocarbons that give the following products on oxidative cleavage by $K M n O_{4}$ or $O_{3}$ :
$H O O C (C H_{2})_{8} C O O H$

Q. Propose structure/structures for the hydrocarbon that gives the following products on oxidative cleavage by

K M n O_{4} / H^{\oplus}

Q. Propose structures for the hydrocrbon that gives the following products on oxidative cleavage by

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Q. Assertion :Treatment of one mole of

2

-butene with

O_{3}

followed by.work-up with

H_{2} O_{2}

gives

2

moles of acetic acid. Reason:

H_{2} O_{2}

bring about oxidative cleavage of intermediate cyanide.

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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 $K M n O_{4}$ or $O_{3}$ :