Chapter 20, Problem 20.66P

Interpretation Introduction

(a)

Interpretation:

A synthesis of given compound by using the acetyl chloride is to be determined.

Concept introduction:

${\text{LiAlH}}_{\text{4}}$ is the reducing agent. It converts the acid chloride or anhydrides into a primary alcohol. The corresponding alcohol is formed from the reduction of carbonyl a compound. And after removing the hydrogen from alcohol to get alkoxide. Alkoxide ion attack on the carbonyl carbon of the acid chloride and expels the good leaving group and forms the ester as a product.

Interpretation Introduction

(b)

Interpretation:

A synthesis of a given compound by using the acetyl chloride is to be determined.

Concept introduction:

Alkoxide is the convert to alkyl bromide after reaction with ${\text{H}}_{\text{3}}{\text{O}}^{\text{+}}$ and ${\text{PBr}}_3$. Alkyl bromide converts to alkyl lithium in the presence of lithium. Gilman reagents react with the organic halides and substitute the halide group with alkyl or aryl group. Then after the reaction in the presence of acid halide to form a ketone. Finally, reduction of the ketone in alcohol in the presence of the reducing agent ${\text{NaBH}}_{\text{4}}$ and ethanol.

Interpretation Introduction

(c)

Interpretation:

A synthesis of a given compound by using the acetyl chloride is to be determined.

Concept introduction:

Alkyl lithium reagent is the reducing reagent and it convert carboxylic ester into tertiary alcohol followed by acid work.

Interpretation Introduction

(d)

Interpretation:

A synthesis of a given compound by using the acetyl chloride is to be determined.

Concept introduction:

Alkoxide is the convert to alkyl bromide after reaction with ${\text{H}}_{\text{3}}{\text{O}}^{\text{+}}$ and ${\text{PBr}}_3$. Alkyl bromide converts to alkyl lithium in the presence of lithium. Gilman reagents react with the organic halides and substitute the halide group with alkyl or aryl group. Then after the reaction in the presence of acid halide to form a ketone with expelling the halide ion.

Interpretation Introduction

(e)

Interpretation:

A synthesis of a given compound by using the acetyl chloride is to be determined.

Concept introduction:

${\text{NaNH}}_{\text{2}}$ is the strong base and it will deprotonate functional groups with acidic proton such as carbonyl compounds like ester and ketone. Acid halide reacts with sodium amide to form acyl amide. ${\text{LiAlH}}_{\text{4}}$ is the reducing agent. It converts the acyl amide into amine with water.

Interpretation Introduction

(f)

Interpretation:

A synthesis of a given compound by using the acetyl chloride is to be determined.

Concept introduction:

NaOH is a strong base it converts the acyl chloride into carboxylate ion. Carboxylate ion reacts with acyl chloride to form acetic anhydride. Here nucleophilic substitution reaction, acetate ion is acting as a nucleophile.