Chapter 10, Problem 10.71P

Interpretation Introduction

Interpretation:

The sequence of reactions that will exclusively produce $\text{(1-ethylpropoxy)cyclopentane}$ from the same two alcohols given in Problem 10.48 is to be proposed.

Concept introduction:

Under acidic conditions, two molecules of an alcohol react to produce a symmetrical ether. If a mixture of alcohols is used, a total of three ethers – two symmetrical and one non-symmetrical – are produced.

If only a particular ether is to be produced, a different reaction called Williamson ether synthesis needs to be used. In Williamson ether synthesis, a primary alkyl halide is treated with an alkoxide anion to exclusively form one ether. Both the alkyl halide and the alkoxide anion can be generated from the alcohols, the first by treating the corresponding alcohol with ${\text{PBr}}_3$ and the second by treating the corresponding alcohol with a strong base.