Chapter 18, Problem 18.50P

Interpretation Introduction

Interpretation:

A synthesis of diethylcarbamazine from the given starting materials has to be given.

Concept introduction:

Retro synthesis: It is a technique of planning an organic synthesis by the reverse approach. In this technique, the starting materials are obtained by cleaving the target molecule into logical synthons. Synthons are precursor fragments of the target compound when it is cleaved. Depending on the stability, the synthons are classified as logical and illogical synthons. Logical synthons are highly stable precursor fragments, and illogical synthons are less stable precursor fragments of the target compound.

Base catalysed ring opening of epoxide:

The nucleophile will attack at the less substituted position under basic conditions and then the alkoxide ion gets proton from alcohol which form the product.

Acid chlorides are most often prepared by treating a carboxylic acid with thionyl chloride.

Chloroformates:

They are the class of organic compounds which are colourless and having a formula $\text{ROC}\left(\text{O}\right)\text{Cl}$

Reaction of Chloroformates with amines:

$\text{ROC}\left(\text{O}\right)\text{Cl}\text{+}{\text{H}}_{\text{2}}{\text{NR}}^{\text{'}}\to \text{ROC}\left(\text{O}\right)\text{-N}\left(\text{H}\right){\text{R}}^{\text{'}}\text{+}\text{HCl}$

The product will be carbamates.