Chapter 12, Problem 12.30P

Interpretation Introduction

Interpretation: The product formed when the given diene is treated with ${\text{O}}_{\text{3}}$ followed by ${\text{CH}}_{\text{3}}{\text{SCH}}_{\text{3}}$ is to be drawn.

Concept introduction: In presence of ozone and ${\text{CH}}_{\text{3}}{\text{SCH}}_{\text{3}}$, oxidative cleavage occurs. In oxidative cleavage both the sigma and pi bond of the alkene is broken and two carbonyl compounds are formed. Depending upon alkyl substituents aldehyde or ketone is formed. When ozone is added to the alkene, unstable intermediate molozonide is formed which rearranges to ozonide. This ozonide is reduced to form two carbonyl compounds in presence of ${\text{CH}}_{\text{3}}{\text{SCH}}_{\text{3}}$.