Chapter 20, Problem 20.40P

Draw the product formed when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with each compound.

a. ${\text{CH}}_{\text{2}}=\text{O}$, then ${\text{H}}_{\text{2}}\text{O}$ e. ${\text{CH}}_{\text{3}}\text{COOH}$ h., then ${\text{H}}_{\text{2}}\text{O}$

b., then ${\text{H}}_{\text{2}}\text{O}$ f. $\text{HC}\equiv \text{CH}$ i. ${\text{D}}_{\text{2}}\text{O}$

c. ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{COCl}$, then ${\text{H}}_{\text{2}}\text{O}$ g. ${\text{CO}}_{\text{2}}$, then ${\text{H}}_{\text{3}}{\text{O}}^{+}$ j., then ${\text{H}}_{\text{2}}\text{O}$

d. ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{COOCH}}_{\text{3}}$, then ${\text{H}}_{\text{2}}\text{O}$

Interpretation Introduction

(a)

Interpretation: The product formed when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound 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 a molecule with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 20.40P

The product formed when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound is given below.

Explanation of Solution

The chemical equation when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound is shown below.

Figure 1

The above equation shows that formaldehyde reacts with ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ in the presence of water to form butan $-1-$ ol.

Conclusion

The product formed when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound is shown in Figure 1.

Interpretation Introduction

(b)

Interpretation: The product formed when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound 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 a molecule with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 20.40P

The product formed when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound is given below.

Explanation of Solution

The chemical equation when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound is shown below.

Figure 2

The above reaction indicates that that cyclopentanone reacts with ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ in the presence of water to form $1-$ propylcyclopentanol.

Conclusion

The product formed when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound is drawn in Figure 2.

Interpretation Introduction

(c)

Interpretation: The product formed when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound 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 a molecule with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 20.40P

The product formed when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound is given below.

Explanation of Solution

The chemical equation when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound is shown below.

Figure 3

The above equation shows that propionyl chloride reacts with two equivalents of ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ in the presence of water to form $4-$ ethylheptan $-4-$ ol.

Conclusion

The product formed when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound is shown in Figure 3.

Interpretation Introduction

(d)

Interpretation: The product formed when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound 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 a molecule with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 20.40P

The product formed when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound is given below.

Explanation of Solution

The chemical equation when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound is shown below.

Figure 4

The above equation shows that methyl propionate reacts with two equivalents of ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ in the presence of water to form $4-$ ethylheptan $-4-$ ol.

Conclusion

The product formed when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound is shown in Figure 4.

Interpretation Introduction

(e)

Interpretation: The product formed when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound 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 a molecule with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 20.40P

The products formed when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ treated with the given compound are given below.

Explanation of Solution

The chemical equation when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ treated with the given compound is shown below.

Figure 5

The above equation shows that acetic acid reacts with ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ in the presence of water to form magnesium acetate bromide and propane.

Conclusion

The product formed when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound is shown in Figure 5.

Interpretation Introduction

(f)

Interpretation: The product formed when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound 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 a molecule with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 20.40P

The products formed when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ treated with the given compound are given below.

Explanation of Solution

The chemical equation when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ treated with the given compound is shown below.

Figure 6

The above equation shows that ethyne reacts with ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ in the presence of water to form propane and ethylmagnesium bromide.

Conclusion

The product formed when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound is shown in Figure 6.

Interpretation Introduction

(g)

Interpretation: The product formed when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound 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 a molecule with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 20.40P

The product formed when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound is given below.

Explanation of Solution

The chemical equation when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound is shown below.

Figure 7

The above equation shows that propylmagnesium bromide reacts with ${\text{CO}}_2$ in the presence of hydronium ion to form butyric acid.

Conclusion

The product formed when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound is shown in Figure 7.

Interpretation Introduction

(h)

Interpretation: The product formed when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound 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 a molecule with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 20.40P

The product formed when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound is given below.

Explanation of Solution

The chemical equation when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound is shown below.

Figure 8

The above equation shows that $2,2-$ dimethyloxiranereacts with ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ in the presence of water to form $2-$ methylhexan $-2-$ ol.

Conclusion

The product formed when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound is shown in Figure 8.

Interpretation Introduction

(i)

Interpretation: The product formed when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound 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 a molecule with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 20.40P

The product formed when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound is given below.

Explanation of Solution

The chemical equation when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound is shown below.

Figure 9

The above equation shows that propylmagnesium bromide reacts with ${\text{D}}_{\text{2}}\text{O}$ to produce deuterated alkane.

Conclusion

The product formed when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound is shown in Figure 9.

Interpretation Introduction

(j)

Interpretation: The product formed when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound is to be drawn. 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 a molecule with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 20.40P

The product formed when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound is given below.

Explanation of Solution

The chemical equation when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound is shown below.

Figure 10

The compound $3-$ methylcyclohex-2-enone reacts with ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ in the presence of water to produce $3-$ methyl $-1-$ propyl cyclohex $-2-$ enol.

Conclusion

The product formed when ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$ is treated with the given compound is shown in Figure 10.