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Alkyne Oxidative Cleavage
Alkyne Oxidative Cleavage
10. Addition Reactions / Alkyne Oxidative Cleavage / Problem 4

An unknown compound X absorbs 5 equivalents of hydrogen to give n-butylcyclopentane when it is treated with hydrogen gas in the presence of a platinum catalyst. The following products are obtained when X is treated with an excess of ozone, followed by dimethyl sulfide and water.


Propose a structure for the unknown compound X. Is there any uncertainty in the structure that you proposed?

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