an-unknown-compound-x-absorbs-5-equivalents-of-hydrogen-to-give-n-butylcyclopent

Question

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.
Chemical reaction showing ozonolysis of an alkyne to form various products.

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

Accepted Answer

Whether the alkene is cis or trans is not certain.

Structure of a compound with a triple bond and a cyclopentane ring, highlighting a different double bond position.

Answer

The position of the triple bond in the proposed structure is not certain.

Structure of a compound with a triple bond and a cyclopentane ring.

Answer

The position of the double bonds in the proposed structure is not certain.

Structure of a compound with a triple bond and a cyclopentane ring, showing a different double bond position.

Answer

Whether compound X has a triple bond is not certain.

Structure of a compound with a triple bond and a cyclopentane ring, showing another variation of double bond position.

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