Chapter 20, Problem 20.39P

Interpretation Introduction

(a)

Interpretation: The product formed by the treatment of $1$-bromobutane with the given reagent is to be drawn.

Concept introduction: The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of products with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 20.39P

The product formed by the treatment of $1$-bromobutane with the given reagent is,

Figure 1

Explanation of Solution

The halogen group of alkyl halide is replaced by $\text{Li}$ when it is treated with $\text{Li}$. In the given reaction, one $\text{Li}$ atom takes the position of halogen and the other $\text{Li}$ atom forms bond with halogen. The product formed by the treatment of $1$-bromobutane with the given reagent is shown in Figure 2.

Figure 2

Conclusion

The product formed by the treatment of $1$-bromobutane with the given reagent is shown in Figure 2.

Interpretation Introduction

(b)

Interpretation: The product formed by the treatment of $1$-bromobutane with the given reagent is to be drawn.

Concept introduction: The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of products with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 20.39P

The product formed by the treatment of $1$-bromobutane with the given reagent is,

Figure 3

Explanation of Solution

The halogen group of alkyl halide forms bond with $\text{Mg}$ when it is treated with $\text{Mg}$. In the given reaction, $1$-bromobutaneon reaction with $\text{Mg}$ in solvent ${\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\right)}_{\text{2}}\text{O}$ form Grignard reagent. The product formed by the treatment of $1$-bromobutane with the given reagent is shown in Figure 4.

Figure 4

Conclusion

The product formed by the treatment of $1$-bromobutane with the given reagent is shown in Figure 4.

Interpretation Introduction

(c)

Interpretation: The product formed by the treatment of $1$-bromobutane with the given reagent is to be drawn.

Concept introduction: The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of products with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 20.39P

The product formed by the treatment of $1$-bromobutane with the given reagent is,

Figure 5

Explanation of Solution

The halogen group of alkyl halide is replaced by $\text{Li}$ when it is treated with $\text{Li}$. In the given reaction, one $\text{Li}$ atom takes the position of halogen and the other $\text{Li}$ atom form bond with halogen. The alkyl lithium on further reaction with $\text{CuI}$ forms Gilman reagent. The product formed by the treatment of $1$-bromobutane with the given reagent is shown in Figure 6.

Figure 6

Conclusion

The product formed by the treatment of $1$-bromobutane with the given reagent isshown in Figure 6.

Interpretation Introduction

(d)

Interpretation: The product formed by the treatment of $1$-bromobutane with $\text{Li}\left(\text{2}\text{equiv}\right)$ and then ${\text{H}}_{\text{2}}\text{O}$ is to be drawn.

Concept introduction: The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of products with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 20.39P

The product formed by the treatment of $1$-bromobutane with $\text{Li}\left(\text{2}\text{equiv}\right)$ and then ${\text{H}}_{\text{2}}\text{O}$ is,

Figure 7

Explanation of Solution

The product formed by the reaction of $1$-bromobutanewith $\text{Li}$ ($2$ equivalent) is ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{Li}$. The organolithium compounds on reaction with ${\text{H}}_{\text{2}}\text{O}$ gives alkane and $\text{LiOH}$. Therefore, the product formed by the treatment of $1$-bromobutane with the given reagent is shown below.

Figure 8

Conclusion

The product formed by the treatment of $1$-bromobutane with $\text{Li}\left(\text{2}\text{equiv}\right)$ and then ${\text{H}}_{\text{2}}\text{O}$ isshown in Figure 8.

Interpretation Introduction

(e)

Interpretation: The product formed by the treatment of $1$-bromobutane with $\text{Mg}$ in solvent ${\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\right)}_{\text{2}}\text{O}$ and then ${\text{D}}_{\text{2}}\text{O}$ is to be drawn.

Concept introduction: The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of products with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 20.39P

The product formed by the treatment of $1$-bromobutane with $\text{Mg}$ and then ${\text{D}}_{\text{2}}\text{O}$ is,

Figure 9

Explanation of Solution

The product formed by the reaction of $1$-bromobutane with $\text{Mg}$ is ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$. The Grignardreagent on reaction with ${\text{D}}_{\text{2}}\text{O}$ gives alkanein which one of the hydrogen atom is replaced by $\text{D}$. Therefore, the product formed by the treatment of $1$-bromobutane with the given reagent is shown below.

Figure 10

Conclusion

The product formed by the treatment of $1$-bromobutane with $\text{Mg}$ in solvent ${\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\right)}_{\text{2}}\text{O}$ and then ${\text{D}}_{\text{2}}\text{O}$ is shown in Figure 10.

Interpretation Introduction

(f)

Interpretation: The product formed by the treatment of $1$-bromobutane with $\text{Li}\left(\text{2}\text{equiv}\right)$ and then ${\text{CH}}_{\text{3}}\text{C}\equiv \text{CH}$ is to be drawn.

Concept introduction: The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of products with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 20.39P

The product formed by the treatment of $1$-bromobutane with $\text{Li}\left(\text{2}\text{equiv}\right)$ and then ${\text{CH}}_{\text{3}}\text{C}\equiv \text{CH}$ is,

Figure 11

Explanation of Solution

The product formed by the reaction of $1$-bromobutane with $\text{Li}$ ($2$ equivalent) is ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{Li}$. The organolithium compounds on reaction with alkyne form lithium acetylideand alkane by abstracting hydrogen atom from alkyne. Therefore, the product formed by the treatment of $1$-bromobutane with the given reagent is shown below.

Figure 12

Conclusion

The product formed by the treatment of $1$-bromobutane with $\text{Li}\left(\text{2}\text{equiv}\right)$ and then ${\text{CH}}_{\text{3}}\text{C}\equiv \text{CH}$ is shown in Figure 12.