Chapter 12, Problem 12.53P

Interpretation Introduction

(a)

Interpretation: The products formed by the reaction of squalene with ${\text{O}}_3$ followed by $\text{Zn},{\text{H}}_{\text{2}}\text{O}$ are to be drawn.

Concept introduction: In the 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. 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 products formed when the given compounds are treated with ozone and $\text{Zn},{\text{H}}_{\text{2}}\text{O}$ are to be drawn.

Concept introduction: In the 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. 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 products formed when the given compounds are treated with ozone and $\text{Zn},{\text{H}}_{\text{2}}\text{O}$ are to be drawn.

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. 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 $\text{Zn},{\text{H}}_{\text{2}}\text{O}$.