Chapter 21, Problem 21.60P

What reagents are needed to convert each compound to $2-\text{butanone}\left({\text{CH}}_{\text{3}}{\text{COCH}}_{\text{2}}{\text{CH}}_{\text{3}}\right)$?

a. b. c. ${\text{CH}}_3\text{COCl}$ d. ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{C}\equiv \text{CH}$ e. ${\text{CH}}_{\text{3}}\text{C}\equiv {\text{CCH}}_{\text{3}}$

Interpretation Introduction

(a)

Interpretation: The reagents needed to convert given compound to $2-\text{butanone}$ are to be predicted.

Concept introduction: Potassium dichromate is a strong oxidizing agent. Potassium dichromate is used in many organic reactions to oxidize organic compounds. Chromium atom present in Potassium chromate itself gets reduced from oxidation state six to a lower oxidation state and oxidizes the other compound.

Answer to Problem 21.60P

The reagent needed to convert given compound to $2-\text{butanone}$ is ${\text{K}}_{\text{2}}{\text{Cr}}_{\text{2}}{\text{O}}_{\text{7}}$.

Explanation of Solution

The given compound can be converted into $2-\text{butanone}$ using ${\text{K}}_{\text{2}}{\text{Cr}}_{\text{2}}{\text{O}}_{\text{7}}$. The oxidation reaction between the given compound and ${\text{K}}_{\text{2}}{\text{Cr}}_{\text{2}}{\text{O}}_{\text{7}}$ is represented as,

Figure 1

Conclusion

The reagent needed to convert given compound to $2-\text{butanone}$ is ${\text{K}}_{\text{2}}{\text{Cr}}_{\text{2}}{\text{O}}_{\text{7}}$.

Interpretation Introduction

(b)

Interpretation: The reagents needed to convert given compound to $2-\text{butanone}$ are to be predicted.

Concept introduction: Gilman reagent is an organometallic compound. Gilman reagent is lithium dialkylcuprate that is used to add alkyl group in an organic compound. Gilman reagent reacts with any organic halide and substitute the halide group by an alkyl group.

Answer to Problem 21.60P

The reagents needed to convert given compound to $2-\text{butanone}$ are ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{CuLi}$ and ${\text{H}}_{\text{2}}\text{O}$.

Explanation of Solution

The given compound can be converted into $2-\text{butanone}$ using ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{CuLi}$ and ${\text{H}}_{\text{2}}\text{O}$. The reaction between the given compound, ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{CuLi}$ and ${\text{H}}_{\text{2}}\text{O}$ is represented as,

Figure 2

Conclusion

The reagents needed to convert given compound to $2-\text{butanone}$ are ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{CuLi}$ and ${\text{H}}_{\text{2}}\text{O}$.

Interpretation Introduction

(c)

Interpretation: The reagents needed to convert given compound to $2-\text{butanone}$ are to be predicted.

Concept introduction: Gilman reagent is an organometallic compound. Gilman reagent is lithium dialkylcuprate that is used to add alkyl group in an organic compound. Gilman regent reacts with any organic halide and substitute the halide group by alkyl group.

Answer to Problem 21.60P

The reagent needed to convert given compound to $2-\text{butanone}$ is ${\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\right)}_{\text{2}}\text{CuLi}$ and ${\text{H}}_{\text{2}}\text{O}$.

Explanation of Solution

The given compound can be converted into $2-\text{butanone}$ using ${\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\right)}_{\text{2}}\text{CuLi}$ and ${\text{H}}_{\text{2}}\text{O}$. The reaction between the given compound, ${\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\right)}_{\text{2}}\text{CuLi}$ and ${\text{H}}_{\text{2}}\text{O}$ is represented as,

Figure 3

Conclusion

The reagent needed to convert given compound to $2-\text{butanone}$ is ${\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\right)}_{\text{2}}\text{CuLi}$ and ${\text{H}}_{\text{2}}\text{O}$.

Interpretation Introduction

(d)

Interpretation: The reagents needed to convert given compound to $2-\text{butanone}$ are to be predicted.

Concept introduction: When an alkyne reacts with mercury sulfate solution in a strong acidic medium a ketone is formed and this reaction is known as the oxymercuration of alkynes. The oxymercuration of alkyne is a very effective method to convert an alkyne into a ketone.

Answer to Problem 21.60P

The reagent needed to convert given compound to $2-\text{butanone}$ is ${\text{HgSO}}_{\text{4}}$, ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ and ${\text{H}}_{\text{2}}\text{O}$.

Explanation of Solution

The given compound can be converted into $2-\text{butanone}$ using ${\text{HgSO}}_{\text{4}}$, ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ and ${\text{H}}_{\text{2}}\text{O}$. The oxymercuration reaction between the given compound, ${\text{HgSO}}_{\text{4}}$, ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ and ${\text{H}}_{\text{2}}\text{O}$ is represented as,

Figure 4

Conclusion

The reagent needed to convert given compound to $2-\text{butanone}$ is ${\text{HgSO}}_{\text{4}}$, ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ and ${\text{H}}_{\text{2}}\text{O}$.

Interpretation Introduction

(e)

Concept introduction: When an alkyne reacts with mercury sulfate solution in a strong acidic medium a ketone is formed and this reaction is known as the oxymercuration of alkynes. The oxymercuration of alkyne is a very effective method to convert an alkyne into a ketone.

Answer to Problem 21.60P

The reagent needed to convert given compound to $2-\text{butanone}$ is ${\text{HgSO}}_{\text{4}}$, ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ and ${\text{H}}_{\text{2}}\text{O}$.

Explanation of Solution

The given compound can be converted into $2-\text{butanone}$ using ${\text{HgSO}}_{\text{4}}$, ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ and ${\text{H}}_{\text{2}}\text{O}$. The oxymercuration reaction between the given compound, ${\text{HgSO}}_{\text{4}}$, ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ and ${\text{H}}_{\text{2}}\text{O}$ is represented as,

Figure 5

Conclusion

The reagent needed to convert given compound to $2-\text{butanone}$ is ${\text{HgSO}}_{\text{4}}$, ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ and ${\text{H}}_{\text{2}}\text{O}$.