Chapter 19, Problem 19.58P

Interpretation Introduction

(a)

Interpretation:

The major product for the given reaction is to be drawn.

Concept introduction:

Lithium dialkylcuprate, ${\left(\text{R}\right)}_{\text{2}}\text{CuLi}$ is called a Gilman reagent which possesses a weak nucleophile, ${\text{R}}^{\text{-}}$. It is used to a common coupling reaction with an alkyl halide, $\text{R’-X}$. Where, R: alkyl, vinyl or aryl group and R’: primary alkyl, secondary alkyl, vinyl or an aryl group; and X: halogen atom either of Cl, Br or I. A Gilman reagent does not undergo coupling reaction with a tertiary alkyl halide, instead elimination reaction may occur. The reaction of the Gilman reagent with vinyl halide is stereospecific as the stereochemistry of reactant retained in the product.

Interpretation Introduction

(b)

Interpretation:

The major product for the given reaction is to be drawn.

Concept introduction:

Lithium dialkylcuprate, ${\left(\text{R}\right)}_{\text{2}}\text{CuLi}$ is called a Gilman reagent which possesses a weak nucleophile, ${\text{R}}^{\text{-}}$. It is used to a common coupling reaction with an alkyl halide, $\text{R’-X}$. Where, R: alkyl, vinyl or aryl group and R’: primary alkyl, secondary alkyl, vinyl or an aryl group; and X: halogen atom either of Cl, Br or I. A Gilman reagent does not undergo coupling reaction with a tertiary alkyl halide, instead elimination reaction may occur. The reaction of the Gilman reagent with vinyl halide is stereospecific as the stereochemistry of reactant retained in the product.

Interpretation Introduction

(c)

Interpretation:

The major product for the given reaction is to be drawn.

Concept introduction:

Lithium dialkylcuprate, ${\left(\text{R}\right)}_{\text{2}}\text{CuLi}$, is called a Gilman reagent which possesses a weak nucleophile, ${\text{R}}^{\text{-}}$. It is used to a common coupling reaction with an alkyl halide, $\text{R’-X}$. Where, R: alkyl, vinyl or aryl group and R’: primary alkyl, secondary alkyl, vinyl or an aryl group; and X: halogen atom either of Cl, Br or I. A Gilman reagent does not undergo coupling reaction with a tertiary alkyl halide, instead elimination reaction may occur. The reaction of the Gilman reagent with vinyl halide is stereospecific as the stereochemistry of reactant retained in the product.

Interpretation Introduction

(d)

Interpretation:

The major product for the given reaction is to be drawn.

Concept introduction:

Lithium dialkylcuprate, ${\left(\text{R}\right)}_{\text{2}}\text{CuLi}$, is called a Gilman reagent which possesses a weak nucleophile, ${\text{R}}^{\text{-}}$. It is used to a common coupling reaction with an alkyl halide, $\text{R’-X}$. Where, R: alkyl, vinyl or aryl group and R’: primary alkyl, secondary alkyl, vinyl or an aryl group; and X: halogen atom either of Cl, Br or I. A Gilman reagent does not undergo coupling reaction with a tertiary alkyl halide, instead elimination reaction may occur. The reaction of the Gilman reagent with vinyl halide is stereospecific as the stereochemistry of reactant retained in the product.