Chapter 8, Problem 8.60SP

Interpretation Introduction

Interpretation: The given question stated that unknown X, ${\text{C}}_{\text{5}}{\text{H}}_{\text{9}}\text{Br}$ does not react with bromine or dilute ${\text{KMnO}}_{\text{4}}$. When treated with potassium-tert-butoxide it gives only one product, Y, ${\text{C}}_{\text{5}}{\text{H}}_{\text{8}}$. The X and Y decolorize bromine and changes ${\text{KMnO}}_{\text{4}}$ from purple to brown. Methylcyclobutane is obtained during catalytic hydrogenation of Y, whereas ozonolysis of Y gives dialdehyde Z ${\text{C}}_5{\text{H}}_8{\text{O}}_2$. The structure of X, Y, and Z and the aspect of the structure of X that is still unknown is to be predicted.

Concept introduction: Hydrogenation is a chemical process in which alkene reacts with hydrogen gas in the presence of catalyst like platinum to give saturated compounds.

Ozonolysis is the oxidative cleavage of the double bond, where $\text{C=C}$ bond breaks and hence formation of $\text{C}-\text{O}$ bond takes place. During oxidative cleavage, ketone or aldehyde formation takes place.

To determine: The structure of X, Y, and Z and the aspect of the structure of X that is still unknown.