Chapter 26, Problem 26.1P

Interpretation Introduction

(a)

Interpretation: Product of the given coupling reaction is to be predicted.

Concept introduction: Organocuprate reagents $\left({\text{R}}_{\text{2}}\text{CuLi}\right)$ react with halides of organic compounds, $\text{RX}$ to form coupling products. Only one alkyl group of the organocuprate reagent is transferred to form the product, while the other becomes part of reaction’s by-product.

Answer to Problem 26.1P

The product of the given coupling reaction is octane as shown below.

Explanation of Solution

Species containing copper-carbon bonds are known as organocuprate reagents. These reagents act as nucleophille and react with organic halides to form coupling products that contains new $\text{C-C}$ bond. The reaction of chlorohexane with the organocuprate reagent results in the formation of octene is shown in Figure 1.

Figure 1

Conclusion

Product formed from the coupling reaction is shown in Figure 1.

Interpretation Introduction

(b)

Interpretation: Product of the coupling reaction is to be predicted.

Concept introduction: Organocuprate reagents $\left({\text{R}}_{\text{2}}\text{CuLi}\right)$ react with halides of organic compounds $\text{RX}$ to form coupling products.

Only one alkyl group of the organocuprate reagent is transferred to form the product, while the other becomes part of reaction’s by-product.

Answer to Problem 26.1P

The product of the coupling reaction is $\text{2-methylcyclohexene}$ as shown below.

Explanation of Solution

Species containing copper-carbon bonds are known as organocuprate reagents. These reagents act as nucleophille and react with organic halides to form coupling products that contains new $\text{C-C}$ bond. The reaction of $\text{2-bromocyclohexene}$ with the reagent results in the formation of $\text{2-methylcyclohexene}$ is shown in Figure 2.

Figure 2

Conclusion

Product formed from the coupling reaction is shown in Figure 2.

Interpretation Introduction

(c)

Interpretation: Product of the coupling reaction is to be predicted.

Concept introduction: Organocuprate reagents $\left({\text{R}}_{\text{2}}\text{CuLi}\right)$ react with halides of organic compounds $\text{RX}$ to form coupling products.

Only one alkyl group of the organocuprate reagent is transferred to form the product, while the other becomes part of reaction’s by-product.

Answer to Problem 26.1P

The product of the coupling reaction is $\text{4-butyl-1, 2-dimethoxybenzene}$ as shown below.

Explanation of Solution

Species containing copper-carbon bonds are known as organocuprate reagents. These reagents acting as nucleophille and react with organic halides to form coupling products that contains new $\text{C-C}$ bond. The reaction of $\text{4-iodo-1, 2-dimethoxybenzene}$ with the reagent results in the formation of $\text{4-butyl-1, 2-dimethoxybenzene}$ as shown in Figure 3.

Figure 3

Conclusion

Product formed from the coupling reaction is shown in Figure 3.

Interpretation Introduction

(d)

Interpretation: Product of the coupling reaction is to be predicted.

Concept introduction: Organocuprate reagents $\left({\text{R}}_{\text{2}}\text{CuLi}\right)$ react with halides of organic compounds $\text{RX}$ to form coupling products.

Only one alkyl group of the organocuprate reagent is transferred to form the product, while the other becomes part of reaction’s by-product.

Answer to Problem 26.1P

The product of the coupling reaction is $\text{(Z)-6-ethylidene-2, 7-dimethylnon-2-ene}$ as shown below.

Explanation of Solution

Species containing copper-carbon bonds are known as organocuprate reagents. These reagents act as nucleophille and react with organic halides to form coupling products that contains new $\text{C-C}$ bond. The reaction of $\text{(Z)-6-bromo-2-methylocta-2, 6-diene}$ with the reagent results in the formation of $\text{(Z)-6-ethylidene-2, 7-dimethylnon-2-ene}$ is shown in Figure 4.

Figure 4

Conclusion

Product formed from the coupling reaction is shown in Figure 4.