Chapter 13, Problem 13.46P

Interpretation Introduction

Interpretation:

The synthesis of the target molecule from the given starting material using any other compound containing at the most one carbon is to be determined.

Concept introduction:

In order to synthesize the target molecule, we can use the same reactant for the formation of two different precursors.

Alcohols $\left(\text{OH}\right)$ are treated with phosphorous tribromide $\left({\text{PBr}}_{\text{3}}\right)$ for conversion to alkyl bromide. Hence, in this manner, the poor leaving group is converted to a good leaving group.

In Williamson ether synthesis, alcohols are converted to ethers by using a strong base and an alkyl halide. Primary alkyl halides give the best yield.

Terminal alkyne can be deprotonated and converted to alkynide anion by using a strong base like $\text{NaH}$. Alkynide anion acts as a strong nucleophile.

The nucleophilic substitution reaction between alkynide anion and alkyl halide results in the formation of a new $\text{C-C}$ bond.