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QUESTION
Unknown X, C5H9Br, does not react with bromine or with dilute KMnO4. Upon treatment with potassium t-butoxide, X gives only one product Y, C5H8.
Unknown X, C5H9Br, does not react with bromine or with dilute KMnO4. Upon treatment with potassium t-butoxide, X gives only one product Y, C5H8. Unlike X, Y decolorizes bromine and changes KMnO4 from purple to brown. Catalytic hydrogenation of Y gives methylcyclobutane. Ozonolysis-reduction of Y gives dialdehyde Z, C5H8O2. Propose consistent structures for X, Y, and Z.
