Chapter 12, Problem 12.20P

Interpretation Introduction

(a)

Interpretation: The alkene which yields the given oxidative cleavage products is to be predicted.

Concept introduction: In presence of ozone and $\text{Zn},{\text{H}}_{\text{2}}\text{O}$, 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 $\text{Zn},{\text{H}}_{\text{2}}\text{O}$.

Interpretation Introduction

(b)

Interpretation: The alkene which yields the given oxidative cleavage products is to be predicted.

Concept introduction: In presence of ozone and $\text{Zn},{\text{H}}_{\text{2}}\text{O}$, 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 $\text{Zn},{\text{H}}_{\text{2}}\text{O}$.

Interpretation Introduction

(c)

Interpretation: The alkene which yields the given oxidative cleavage products is to be predicted.

Concept introduction: In presence of ozone and $\text{Zn},{\text{H}}_{\text{2}}\text{O}$, 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 $\text{Zn},{\text{H}}_{\text{2}}\text{O}$.