1. Unknown X, C5H9Br, doesn't react with bromine or with dilute KMnO4. Upon treatment with H3O+ gives only one product, Y, C5H8. Unlike X, Y decolorizes bromine as well as changes KMnO4 from purple to brown. Catalyze hydrogenation of Y gives methylcyclobutane. Ozonolysis/ reduction of Y give dialdehyde Z, C5H8O2. Outline consistent structure for X, Y and Z. Is there any aspect of the structure of X that is still unknown?
2. Halogens are added to alkenes with anti-stereochemistry through the halonium ion mechanism. However, when 1 phenylcyclohexe reacts with chlorine in CCl4, a mixture of cis and trans isomers of products is obtained. Outline a mechanism to explain this lack of strereospecificity.