Chapter 8, Problem 8.18P

Interpretation Introduction

(a)

Interpretation:

The product of $\text{E2}$ elimination involving $\text{D}$ atom, indicated in the given substrate, is to be drawn.

Concept introduction:

Deuterium $\text{D}$ is an isotope of a hydrogen atom, which can also be eliminated along with the leaving group in $\text{E2}$ elimination. In case of $\text{E2}$ elimination, the eliminating groups (leaving group and $\text{H}$ or $\text{D}$) must be anti to each other. If the substrate has both hydrogen atom and deuterium atom attached to the carbon adjacent to the leaving group, then elimination can occur in two ways. In one way, hydrogen atom is eliminated along with the leaving group, and in the other way, the $\text{D}$ atom is eliminated along with the leaving group, thus forming a mixture of diastereomer.

Interpretation Introduction

(b)

Interpretation:

The product of $\text{E2}$ elimination involving $\text{H}$ atom indicated in the given substrate is to be drawn.

Concept introduction:

Deuterium $\text{D}$ is an isotope of hydrogen atom, which can also be eliminated along with the leaving group in $\text{E2}$ elimination. In case of $\text{E2}$ elimination, the eliminating groups (leaving group and $\text{H}$ or $\text{D}$) must be anti to each other. If the substrate has both, hydrogen atom and deuterium atom, attached to the carbon adjacent to the leaving group, then elimination can occur two ways. In one way, hydrogen atom is eliminated along with the leaving group, and in the other way, the $\text{D}$ atom is eliminated along with the leaving group, thus forming a mixture of diastereomer.