Chapter 17, Problem 3LGP

Interpretation Introduction

Interpretation:

The details of the mechanism for the reaction between mixed anhydride and Z-Ala-Leu, and how carbon dioxide and ethanol are formed in the mechanisms are to be discussed.

Concept introduction:

The reaction between nucleophile and acyl compounds is called nucleophilic acyl substitution.

Nucleophilic acyl substitution describe a class of substitution reactions involving nucleophiles and acyl compounds. In this type of reaction, a nucleophile—such as an alcohol, amine, or enolate—displaces the leaving group of an acyl derivative—such as an acid halide, anhydride, or ester.

A mixed anhydride is a carboxylic acid anhydride.

Acid chlorides react with amines to form amides.

The carboxylic acid is converted into acid chlorides in the presence of thionyl chloride.

Decarboxylation is the loss of carbon dioxide.