Chapter 24, Problem 24.45SP

(a)

Interpretation Introduction

To determine: The reason corresponding to the fact that an NHS ester is much more reactive than a simple alkyl ester.

Interpretation: The reason corresponding to the fact that an NHS ester is much more reactive than a simple alkyl ester is to be stated.

Concept introduction: The compound containing a good leaving group that has molecular formula ${\text{C}}_{\text{4}}{\text{H}}_{\text{5}}{\text{NO}}_{\text{3}}$ and is used as an activating reagent for carboxylic acid is known as N-hydroxysuccinimide (NHS). It is slightly acidic in nature.

(b)

Interpretation Introduction

To determine: The mechanism for the given reaction that coverts an acid to NHS ester.

Interpretation: The mechanism for the given reaction that coverts an acid to NHS ester is to be predicted.

Concept introduction: The compound containing a good leaving group that has molecular formula ${\text{C}}_{\text{4}}{\text{H}}_{\text{5}}{\text{NO}}_{\text{3}}$ and is used as an activating reagent for carboxylic acid is known as N-hydroxysuccinimide (NHS). It is slightly acidic in nature.

(c)

Interpretation Introduction

To determine: The mechanism for the reaction of NHS ester with an amine, $\text{R}-{\text{NH}}_{\text{2}}$.

Interpretation: The mechanism for the reaction of NHS ester with an amine, $\text{R}-{\text{NH}}_{\text{2}}$ is to be predicted.

Concept introduction: The compound containing a good leaving group that has molecular formula ${\text{C}}_{\text{4}}{\text{H}}_{\text{5}}{\text{NO}}_{\text{3}}$ and is used as an activating reagent for carboxylic acid is known as N-hydroxysuccinimide (NHS). It is slightly acidic in nature.