Chapter 18, Problem 18.95P

Interpretation Introduction

Interpretation:

The synthesis of $\text{2}-\text{methylhexane}$ from $\text{hex-4-en-3-one}$ and any other necessary reagents is to be given.

Concept introduction:

Beta-alkylation of $\text{α,β}$-unsaturated carbonyl compounds is achieved using Gilman reagent (${\text{R}}_{\text{2}}\text{CuLi}$). The $\text{α,β}$-unsaturated carbonyl compounds undergo a conjugate addition ($\text{1, 4-addition}$) with the Gilman reagent (${\text{R}}_{\text{2}}\text{CuLi}$) in which the nucleophile ${\text{R}}^{-}$ exclusively adds at the beta-carbon of the $\text{α,β}$-unsaturated carbonyl compound via conjugate addition. The carbonyl carbon can be converted to ${\text{CH}}_2$ using a Wolf-Kishner reduction or a Clemmensen reduction or Raney-nickel reduction. A retrosynthetic approach is useful in planning a synthesis of the target molecule, using the given starting molecule and any other reagents.