Help with Ozonolysis - Organic Chemistry

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Question

Which substrate, when subjected to ozonolysis followed by treatment with dimethyl sulfide, would give only one hydrocarbon product?

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Answer

Ozonolysis is essentially used to cleave a compound at the location of a double bond. For the result to be a single product, the cleavage must occur at a point of symmetry.

4-octene, a symmetrical alkene, would give two equivalents of butanal upon ozonolysis. All of the other compounds are unsymmetrical and would give at least two different non-identical products.

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