Chapter 19.3, Problem 19.6P

(a)

Interpretation Introduction

Interpretation:

The conversion of benzoic acid to 3-methyl-1-phenyl-1-butanone by the help of a lithium diorganocopper reagent has to be shown.

Concept introduction:

Gilman reagent:

It is generally represented as ${\text{R}}_{\text{2}}\text{CuLi}$ and it is a lithium and copper reagent which is used to form a new carbon-carbon bond formation in organic synthesis.

Reaction of Gilman reagent with acid chlorides:

(b)

Interpretation Introduction

Interpretation:

The conversion of benzoic acid to 3-methyl-1-phenyl-1-butanone by the help of a lithium diorganocopper reagent has to be shown.

Concept introduction:

When two molecules of an ester undergo condensation, then it is called claisen condensation. Like in aldol reaction, in claisen condensation one molecule is a nucleophile and the other molecule is an electrophile.

A claisen condensation reaction is a reversible reaction and occurs in the presence of a strong base.

The first step of claisen condensation is the removal of a proton from alpha carbon by a base and then the addition of enolate ion formed to the second ester molecule forming a β-ketoester.