Chapter 26.4, Problem

Interpretation Introduction

Interpretation:

A retrosynthetic analysis to plan a synthesis of isoleucine from $\text{2-methyl-1-butanol}$ is to be used and equations for the synthesis are to be written.

Concept Introduction:

Amino acids can be synthesized by the reaction of an aldehyde with ${\text{NH}}_{\text{4}}\text{Cl and NaCN}$. It is known as the Strecker synthesis.

This is a double nucleophilic addition reaction that converts the aldehyde to an amino acid having one more carbon atom.

Hydrolysis of the nitrile group converts the nitrile to the carboxylic acid group.

Aldehydes can be obtained by the oxidation of primary alcohols with pyridinium chlorochromate. This reagent stops the oxidation at the aldehyde stage.