Chapter 23, Problem 47PP

Interpretation Introduction

Interpretation:

The synthesis of decane from $\text{1-}$ pentene should be identified using Corey–Posner/Whitesides–House reaction.

Concept Introduction:

Preparation of organolithium: They are prepared by reaction of organohalide in presence of two equivalents of $Li$.

    $\text{R-X}\stackrel{\text{Li}\left(\text{2eq}\right)}{\to }\text{R-Li + LiX}$

Preparation of Grignard reagents: They are prepared by reaction of organohalide in presence $Mg$ in ether solvent.

    $\text{R-X}\underset{E{t}_{2}O}{\overset{Mg}{\to }}\text{R-Mg-X}$

Reaction between Grignard reagent and water: Grignard reagents are strong bases which in presence of water forms hydrocarbon easily.

Corey–Posner–Whitesides–House reaction: It involves reaction between ${\text{R}}_{\text{2}}\text{CuLi}$ and organyl halide that results in formation of alkane and organocopper and lithium halide species as byproducts.

Gillman reagent: The lithium copper reagent compound $(R_{2}CuLi)$ are very useful because unlike Grignard reagent and organolithium reagents, they react with organic halides to replace the halide group with an alkyl (R) group.

• Organocuprate $(R_{2}CuLi)$ are also known as Gilman Reagent.
• It is prepared from an organolithium compound by reaction with cuprous iodide in diethyl ether or THF as follows.

  

Hydrogenation: It involves addition of hydrogen to another compound in presence of $H_2$ with catalyst namely nickel, palladium or platinum.