Chapter 21, Problem 21.12P

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.

Answer to Problem 21.12P

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 ${\text{CH}}_{\text{3}}\text{COCl}$, and ${\text{AlCl}}_{\text{3}}$.

Explanation of Solution

The given compound is benzene. The conversion of benzene into acetophenone involves acylation of benzene ring.

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. Thus, 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 ${\text{CH}}_{\text{3}}\text{COCl}$, and ${\text{AlCl}}_{\text{3}}$.

Conclusion

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 ${\text{CH}}_{\text{3}}\text{COCl}$, and ${\text{AlCl}}_{\text{3}}$.

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, $\text{CuI}$.

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

Answer to Problem 21.12P

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 $\left[1\right]{\left({\text{CH}}_{\text{3}}\right)}_2\text{CuLi}$, and $\left[2\right]{\text{H}}_2\text{O}$.

Explanation of Solution

The given compound is benzoylchloride.

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, $\text{CuI}$.

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

Thus, 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 $\left[1\right]{\left({\text{CH}}_{\text{3}}\right)}_2\text{CuLi}$, and $\left[2\right]{\text{H}}_2\text{O}$.

Conclusion

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 $\left[1\right]{\left({\text{CH}}_{\text{3}}\right)}_2\text{CuLi}$, and $\left[2\right]{\text{H}}_2\text{O}$.

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 $\left[1\right]\text{Hg}{\left(\text{OAc}\right)}_2;\left[2\right]{\text{H}}_{\text{2}}\text{O,}{\text{Et}}_2\text{O}\text{or}\text{THF}$.

Answer to Problem 21.12P

The reagents that are needed to convert the given compound into acetophenone are $\left[1\right]\text{Hg}{\left(\text{OAc}\right)}_2;\left[2\right]{\text{H}}_{\text{2}}\text{O,}{\text{Et}}_2\text{O}\text{or}\text{THF}$.

Explanation of Solution

The given compound is ethynylbenzene. The conversion of ethynylbenzene into acetophenone involves oxymercuration of ethynylbenzene.

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 $\left[1\right]\text{Hg}{\left(\text{OAc}\right)}_2;\left[2\right]{\text{H}}_{\text{2}}\text{O,}{\text{Et}}_2\text{O}\text{or}\text{THF}$. Thus, the reagents that are needed to convert the given compound into acetophenone are $\left[1\right]\text{Hg}{\left(\text{OAc}\right)}_2;\left[2\right]{\text{H}}_{\text{2}}\text{O,}{\text{Et}}_2\text{O}\text{or}\text{THF}$.

Conclusion

The reagents that are needed to convert the given compound into acetophenone are $\left[1\right]\text{Hg}{\left(\text{OAc}\right)}_2;\left[2\right]{\text{H}}_{\text{2}}\text{O,}{\text{Et}}_2\text{O}\text{or}\text{THF}$.