Chapter 10.11, Problem 33P

Interpretation Introduction

Interpretation:

The preparation of the target molecule in the preceding synthesis using 4-penten-1-ol as the starting material is to be drawn. The reaction that gives higher yield of target molecule has to be given.

Concept Introduction:

Intramolecular reaction: Intramolecular reactions are reactions taking place within one molecule.

S_N2 Reaction: It is a nucleophilic substitution reaction in which the rate determining step depends on both of the molecules involved. The bond making and the bond breaking process happens simultaneously in this reaction resulting in the formation of product with inversed configuration.

Structure of the substrate plays major role in the reactivity of ${\text{S}}_{\text{N}}2$ reaction. If the substrate is more substituted then the rate of the reaction will becomes slower. Since the mechanism of ${\text{S}}_{\text{N}}2$ reaction proceeds through backside attack on the substrate, it depends on steric factor that if more groups attached near the leaving group the reactivity becomes slower. Hence, primary substrate favors ${\text{S}}_{\text{N}}2$ mechanism. The ${\text{S}}_{\text{N}}2$ reactivity increases in molecule with better leaving group.

Williamson ether synthesis: Ether can be synthesized by the reaction of an alkyl halide with an alkoxide ion. This reaction is called the Williamson ether synthesis.

$\text{R-Br}\text{+}{\text{R-O}}^{\text{-}}\to \text{R-O-R}\text{+}{\text{Br}}^{\text{-}}$

Where $\text{R-Br}$ is alkyl halide and ${\text{R-O}}^{\text{-}}$ is alkoxide ion.