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

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

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