Chapter 25, Problem 25.63P

Interpretation Introduction

Interpretation:

When an ether is exposed to air for a prolonged time, it undergoes a radical chain reaction with oxygen gas to form explosive hydroperoxides. The overall reaction between $\text{diethyl ether}$ and ${\text{O}}_{\text{2}}$ is shown. A complete, detailed mechanism for this reaction, including an initiation step, propagation steps, and two possible termination steps is to be provided.

Concept introduction:

A free radical chain reaction involves free radicals in a cyclic sequence of steps, called propagation steps, which are responsible for converting overall reactants into overall products. An initiation step is responsible for producing the free radical that enters the propagation cycle. A termination step removes free radicals from the propagation cycle and is responsible for slowing the overall reaction. Oxygen is a diradical, so it can abstract an $\text{H}$ atom to generate the initial radical that enters the propagation cycle.