Chapter 11, Problem 2LGP

Interpretation Introduction

Interpretation:

The chemically reasonable syntheses possible for $\text{ethyl 2-methylpropyl ether}$(ethyl isobutyl ether) are to be written and the relative merits of the syntheses on the basis of selectivity and efficiency are to be evaluated.

Concept introduction:

In Williamson ether synthesis, between primary alkyl halide and primary alkoxide, the alkyl halide containing the most number of β-hydrogens is more likely to undergo elimination via E2 elimination reactions. Hence, for this type of alkyl halides, the E2 reaction will compete with ${\text{S}}_{\text{N}}\text{2}$ and will affect the selectivity and efficiency of the formation of the desired ether.