Chapter 17, Problem 17.48P

Interpretation Introduction

(a)

Interpretation:

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

Concept introduction:

Organometallic compounds have a polar covalent $\text{C-M}$ bond. For example, the Grignard reagent ($\text{RMgX}$) has a polar $\text{C-Mg}$ bond and an alkyl lithium reagent ($\text{RLi}$) has a polar covalent $\text{C-Li}$ bond. Since carbon is bonded with an electropositive element, it possesses the partial negative charge and acts as the nucleophile as well as the base and can be treated as ${\text{C}}^{\text{-}}$ donor. Thus, it is used to form a new $\text{C-C}$ bond with electrophilic carbon. The nucleophilic part (${\text{R}}^{\text{-}}$) of the organometallic reagent shows a nucleophilic addition reaction with carbonyl compounds. An imine on treatment with the organometallic reagent, Grignard reagent ($\text{RMgX}$) or an alkyl lithium reagent ($\text{RLi}$) followed by the acidic workup yields an amine.

Interpretation Introduction

(b)

Interpretation:

The mechanism of the specified reaction is to be drawn and the major product is to be predicted.

Concept introduction:

Organometallic compounds have a polar covalent $\text{C-M}$ bond. For example, the Grignard reagent ($\text{RMgX}$) has a polar $\text{C-Mg}$ bond and an alkyl lithium reagent ($\text{RLi}$) has a polar covalent $\text{C-Li}$ bond. Since carbon is bonded with an electropositive element, it possesses the partial negative charge and acts as the nucleophile as well as the base and can be treated as ${\text{C}}^{\text{-}}$ donor. Thus it is used to form a new $\text{C-C}$ bond with an electrophilic carbon. The nucleophilic part (${\text{R}}^{\text{-}}$) of the organometallic reagent shows a nucleophilic addition reaction with carbonyl compounds. An imine on treatment with the organometallic reagent, Grignard reagent ($\text{RMgX}$) or an alkyl lithium reagent ($\text{RLi}$) followed by the acidic workup yields an amine.

Interpretation Introduction

(c)

Interpretation:

The mechanism of the specified reaction is to be drawn and the major product is to be predicted.

Concept introduction:

Organometallic compounds have a polar covalent $\text{C-M}$ bond. For example, the Grignard reagent ($\text{RMgX}$) has a polar $\text{C-Mg}$ bond and an alkyl lithium reagent ($\text{RLi}$) has a polar covalent $\text{C-Li}$ bond. Since carbon is bonded with an electropositive element, it possesses the partial negative charge and acts as the nucleophile as well as the base and can be treated as ${\text{C}}^{\text{-}}$ donor. Thus it is used to form a new $\text{C-C}$ bond with an electrophilic carbon. The nucleophilic part (${\text{R}}^{\text{-}}$) of the organometallic reagent shows a nucleophilic addition reaction with carbonyl compounds. An imine on treatment with the organometallic reagent, Grignard reagent ($\text{RMgX}$) or an alkyl lithium reagent ($\text{RLi}$) followed by the acidic workup yields an amine.