Chapter 18.5, Problem 11P

Interpretation Introduction

(a)

Interpretation: The reagents that are needed to convert the given compound into acetophenone $\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{COCH}}_{\text{3}}\right)$ are to be predicted.

Concept introduction: The acylation of aromatic rings is facilitated by Friedel-Crafts acylation reaction. In this reaction, acyl chlorides are used as acylating agents, and Lewis acids like ${\text{AlCl}}_{\text{3}}$ are used as catalyst.

Interpretation Introduction

(b)

Interpretation: The reagents that are needed to convert the given compound into acetophenone $\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{COCH}}_{\text{3}}\right)$ are to be predicted.

Concept introduction: Lithium dialkylcuprate yields ketone, when it is treated with an acyl chloride, followed by hydrolysis. This reagent is obtained from the reaction of organolithium reagent with cuprous iodide, $\text{CuI}$.

$2{\text{R}}^{\text{'}}\text{Li}+\text{CuI}\to {\text{R}}^{\text{'}}{}_2\text{CuLi}+\text{LiI}$

Interpretation Introduction

(c)

Interpretation: The reagents that are needed to convert the given compound into acetophenone $\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{COCH}}_{\text{3}}\right)$ are to be predicted.

Concept introduction: The oxymercuration reaction is an electrophilic addition reaction that converts an alkene into an alcohol and an alkyne into a ketone. The reagents required for this reaction are $\left[1\right]\text{Hg}{\left(\text{OAc}\right)}_2;\left[2\right]{\text{H}}_{\text{2}}\text{O,}{\text{Et}}_2\text{O}\text{or}\text{THF}$.