Chapter 20, Problem 20.25P

Interpretation Introduction

(a)

Interpretation:

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

Concept introduction:

An acid chloride $\left(\text{RCOCl}\right)$, on treatment with a lithium dialkylcparate $\left({\text{R}}_{\text{2}}\text{CuLi}\right)$, produces the corresponding ketone $\left({\text{R}}_{\text{2}}\text{C=O}\right)$. Since lithium dialkylcparate $\left({\text{R}}_{\text{2}}\text{CuLi}\right)$ a weak source of the nucleophile, ${\text{R}}^{-}$ does not react with ketones or aldehydes via direct addition. Esters and amides are more stable than acid chloride; thus they do not react with lithium dialkylcparate $\left({\text{R}}_{\text{2}}\text{CuLi}\right)$. Thus, to convert an amide or ester into a ketone, first convert them into an acid chloride.

Interpretation Introduction

(b)

Interpretation:

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

Concept introduction:

An acid chloride $\left(\text{RCOCl}\right)$, on treatment with a lithium dialkylcparate $\left({\text{R}}_{\text{2}}\text{CuLi}\right)$, produces the corresponding ketone $\left({\text{R}}_{\text{2}}\text{C=O}\right)$. Since lithium dialkylcparate $\left({\text{R}}_{\text{2}}\text{CuLi}\right)$ a weak source of the nucleophile, ${\text{R}}^{-}$ does not react with ketones or aldehydes via direct addition. Esters and amides are more stable than acid chloride; thus they do not react with lithium dialkylcparate $\left({\text{R}}_{\text{2}}\text{CuLi}\right)$. Thus, to convert an amide or ester into a ketone, first convert them into an acid chloride.

Interpretation Introduction

(c)

Interpretation:

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

Concept introduction:

An acid chloride $\left(\text{RCOCl}\right)$, on treatment with a lithium dialkylcparate $\left({\text{R}}_{\text{2}}\text{CuLi}\right)$, produces the corresponding ketone $\left({\text{R}}_{\text{2}}\text{C=O}\right)$. Since lithium dialkylcparate $\left({\text{R}}_{\text{2}}\text{CuLi}\right)$ a weak source of the nucleophile, ${\text{R}}^{-}$ does not react with ketones or aldehydes via direct addition. Esters and amides are more stable than acid chloride; thus they do not react with lithium dialkylcparate $\left({\text{R}}_{\text{2}}\text{CuLi}\right)$. Thus, to convert an amide or ester into a ketone, first convert them into an acid chloride.