Chapter 17, Problem 17.79P

Interpretation Introduction

Interpretation:

How the given synthesis would carry out is to be suggested with necessary reagents.

Concept introduction:

Lithium dialkylcuprates $\left({\text{R}}_{\text{2}}\text{CuLi}\right)$ are weak ${\text{R}}^{\text{-}}$ nucleophiles that favor conjugate addition over direct addition.

Sodium borohydride ${\text{(NaBH}}_{\text{4}})$ is a source of hydride ${\text{H}}^{\text{-}}$ that behaves as a reducing agent and reduces ketones $\left({\text{R}}_{\text{2}}\text{ = CO}\right)$ and aldehydes $\left(\text{RCH = O}\right)$ to alcohols $\left(\text{ROH}\right)$.

Alcohols, when heated with acid, undergo $\text{E1}$, an elimination reaction, to yield the alkene. Heat favors elimination over substitution.