Chapter 17, Problem 17.28P

Interpretation Introduction

(a)

Interpretation:

The major product of the given reaction is to be predicted.

Concept introduction:

Lithium dialkylcuprates, ${\text{R}}_{\text{2}}\text{CuLi}$, are the most common organocuprates. They are also referred to as Gillman reagents. Lithium dialkylcuprate is a source of nucleophile ${\text{R}}^{\text{-}}$, which adds to the $\text{β-}$ carbon of $\text{α,β-}$ unsaturated carbonyl via conjugate addition. The resulting enolate anion is then protonated by ${\text{NH}}_{\text{4}}{}^{\text{+}}$ from ${\text{NH}}_{\text{4}}\text{Cl}$. Lithium dialkylcuprates do not tend to undergo direct addition to a polar $\text{π}$ bond.

Interpretation Introduction

(b)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Lithium dialkylcuprates, ${\text{R}}_{\text{2}}\text{CuLi}$, are the most common organocuprates. They are also referred to as Gillman reagents. Lithium dialkylcuperate is a source of the nucleophile ${\text{R}}^{\text{-}}$, which adds to the $\text{β-}$ carbon of a $\text{α,β-}$ unsaturated carbonyl via conjugate addition. The resulting enolate anion is then protonated by ${\text{NH}}_{\text{4}}{}^{\text{+}}$ from ${\text{NH}}_{\text{4}}\text{Cl}$. Lithium dialkylcuprates do not tend to undergo direct addition to a polar $\text{π}$ bond.

Interpretation Introduction

(c)

Interpretation:

The major product of the given reaction is to be predicted.

Concept introduction:

Lithium dialkylcuprates, ${\text{R}}_{\text{2}}\text{CuLi}$, are the most common organocuperates. They are also referred to as Gillman reagents. This Lithium dialkylcuperate is a source of the nucleophile ${\text{R}}^{\text{-}}$, which adds to the $\text{β-}$ carbon of an $\text{α,β-}$ unsaturated carbonyl via conjugate addition. The resulting enolate anion is then protonated by ${\text{NH}}_{\text{4}}{}^{\text{+}}$ from ${\text{NH}}_{\text{4}}\text{Cl}$. Lithium dialkylcuprates do not tend to undergo direct addition to a polar $\text{π}$ bond.