Question

An unknown compound with empirical formula C3H5 was treated with Br2/CCl4. The bromine solution went from orangish/red to clear immediately at room temperature. Upon treatment with O3 followed by work-up with dimethylsulfide the following products were identified. From the information provided what is/are the most likely structure(s) for this unknown compound.

Answer 1

Answer:

(E)-3-methylpenta-1,3-diene

Explanation:

Bromine water in carbon tetrachloride is used to test for the presence of alkenes. Bromine was added to this unsaturated compound with double bonds, as the reddish color of the solution disappeared. This means bromine was added to the double bonds present in our structure.

Since three products were formed upon ozonolysis, this means we have two double bonds present in our structure, a diene. Besides, a total of 6 carbons are seen in the given structures, so molecular formula of the compound is $C_6H_{10}$.

Ozonolysis occurs when a double bond is broken and oxygen atoms are added to each end of the double bond, that's why we have a total of 3 products.

Our starting material is (E)-3-methylpenta-1,3-diene. You may wish to refer to the file uploaded below which represents the ozonolysis step of breaking the two double bonds and forming the 3 products shown.