Chapter 20, Problem 20.47P

Interpretation Introduction

(a)

Interpretation:

The product with detailed mechanism for the given reaction is to be predicted by identifying whether the reaction has occurred or not.

Concept introduction:

${\text{NaBH}}_{\text{4}}$ is the reducing agent that mainly reduces carbonyls to alcohols. ${\text{NaBH}}_{\text{4}}$ is not that strong reducing agent, and thus, cannot reduce the amide carbonyls.

Interpretation Introduction

(b)

Interpretation:

The product with detailed mechanism for the given reaction is to be predicted by identifying whether the reaction has occurred or not.

Concept introduction:

${\text{LiAlH}}_{\text{4}}$ is the reducing agent that mainly reduces carbonyls to alcohols. ${\text{LiAlH}}_{\text{4}}$ is a strong reducing agent, and thus can reduce the amide to corresponding amine in solvent THF.

Interpretation Introduction

(c)

Interpretation:

The product with detailed mechanism for the given reaction is to be predicted by identifying whether the reaction has occurred or not.

Concept introduction:

${\text{NaBH}}_{\text{4}}$ is the reducing agent mainly reduces carbonyls to alcohols. ${\text{NaBH}}_{\text{4}}$ is not that strong reducing agent, and thus cannot reduce the carboxylic acid’s carbonyls, rather it deprotonates it to carboxylate ion.

Interpretation Introduction

(b)

Interpretation:

The product with detailed mechanism for the given reaction is to be predicted by identifying whether the reaction has occurred or not.

Concept introduction:

${\text{LiAlH}}_{\text{4}}$ is the reducing agent mainly reduces carbonyls to alcohols. ${\text{LiAlH}}_{\text{4}}$ is a strong reducing agent, and thus can reduce the carboxylic acid to aldehyde which on further reduction gives primary alcohol.