10. Addition Reactions
Oxidative Cleavage
Problem 8-60
Textbook Question
Textbook QuestionUnknown 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 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. Is there any aspect of the structure of X that is still unknown?
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