Chapter 26, Problem 26.20P

Draw the products formed in each reaction.

a. c.

b. d.

e. g.

f. h.

Interpretation Introduction

(a)

Interpretation: Product formed from coupling reaction is to be predicted.

Concept introduction: Coupling can be done in many ways by using different reagents. Stereospecific products are also formed in many reactions and the product is addition of two alkyl chains.

Answer to Problem 26.20P

The product formed is,

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 which contains new $\text{C-C}$ bond. The reaction of chlorocyclohexene with the reagent results in the formation of $\text{1-propylcyclohex-1-ene}$ as shown in Figure 1.

Figure 1

Conclusion

The product formed is rightfully stated.

Interpretation Introduction

(b)

Interpretation: Product formed from coupling reaction is to be predicted.

Concept introduction: Coupling can be done in many ways by using different reagents. Stereospecific products are also formed in many reactions and the product is addition of two alkyl chains.

Answer to Problem 26.20P

The product formed is,

Explanation of Solution

Suzuki reaction is a type of coupling reaction. The product formed by the reaction is $\text{R-R}$ and can be formed by the reaction the alkyl halide with organoborane. This reaction is carried out in the presence of a base and is stereospecific. The product of the reaction is $\text{3-m-tolylpyridine}$ as shown in Figure 2.

Figure 2

Conclusion

The product formed is rightfully stated.

Interpretation Introduction

(c)

Interpretation: Product formed from coupling reaction is to be predicted.

Concept introduction: Coupling can be done in many ways by using different reagents. Stereospecific products are also formed in many reactions and the product is addition of two alkyl chains.

Answer to Problem 26.20P

The product formed is,

Explanation of Solution

Heck reaction is a type of coupling reaction. The reaction involves the formation of substituted alkene from an unsaturated halide and an alkene. The catalyst used for this reaction is palladium catalyst. It is a substitution reaction and replacement of H of alkene by alkylhalide takes place. The product of the reaction is $\text{3-(2-(furan-2-yl)vinyl)pyridine}$ as shown in Figure 3.

Figure 3

Conclusion

The product formed is rightfully stated.

Interpretation Introduction

(d)

Interpretation: Product formed from coupling reaction is to be predicted.

Concept introduction: Coupling can be done in many ways by using different reagents. Stereospecific products are also formed in many reactions and the product is addition of two alkyl chains.

Answer to Problem 26.20P

The product formed is,

Explanation of Solution

Species containing copper-carbon bonds are known as organocuprate reagents. The reaction involves these reagents acting as nucleophille and reacts with organic halides to form coupling products and contains new $\text{C-C}$ bond. The product of the reaction is $\text{(E)-undec-2-ene}$ as shown in Figure 4.

Figure 4

Conclusion

The product formed is rightfully stated.

Interpretation Introduction

(e)

Interpretation: Product formed from coupling reaction is to be predicted.

Concept introduction: Coupling can be done in many ways by using different reagents. Stereospecific products are also formed in many reactions and the product is addition of two alkyl chains.

Answer to Problem 26.20P

The product formed is,

Explanation of Solution

Suzuki reaction is a type of coupling reaction. The product formed by the reaction is $\text{R-R}$ and can be formed by the reaction the alkyl halide with organoborane. This reaction is carried out in the presence of a base and is stereospecific. The product of the reaction is $\text{(2E, 4E)-hexa-2, 4-diene}$ as shown in Figure 5.

Figure 5

Conclusion

The product formed is rightfully stated.

Interpretation Introduction

(f)

Interpretation: Product formed from coupling reaction is to be predicted.

Concept introduction: Coupling can be done in many ways by using different reagents. Stereospecific products are also formed in many reactions and the product is addition of two alkyl chains.

Answer to Problem 26.20P

The product formed is,

Explanation of Solution

Heck reaction is a type of coupling reaction. The reaction involves the formation of substituted alkene from an unsaturated halide and an alkene. The catalyst used for this reaction is palladium catalyst. It is a substitution reaction and replacement of H of alkene by alkylhalide takes place. The product of the reaction is $\text{(Z)-methyl 3-(4-methoxyphenyl)acrylate}$ as shown in Figure 6.

Figure 6

Conclusion

The product formed is rightfully stated.

Interpretation Introduction

(g)

Interpretation: Products formed from coupling reaction are to be predicted.

Concept introduction: Coupling can be done in many ways by using different reagents. Stereospecific products are also formed in many reactions and the product is addition of two alkyl chains.

Answer to Problem 26.20P

The products formed are,

Explanation of Solution

Suzuki reaction is a type of coupling reaction. The product formed by the reaction is $\text{R-R}$ and can be formed by the reaction the alkyl halide with organoborane. Organoborane can be prepared by treatment of lithium on compounds of borane and the organoborane thus formed is $\text{dimethyl phenylboronate}$ as shown in Figure 7. The reaction of $\text{dimethyl phenylboronate}$ with bromopropene gives product $\text{(E)-prop-1-enylbenzene}$ as shown in Figure 7.

Figure 7

Conclusion

The products formed are rightfully stated.

Interpretation Introduction

(h)

Interpretation: Product formed from coupling reaction is to be predicted.

Concept introduction: Coupling can be done in many ways by using different reagents. Stereospecific products are also formed in many reactions and the product is addition of two alkyl chains.

Answer to Problem 26.20P

The product formed is,

Explanation of Solution

Suzuki reaction is a type of coupling reaction. The product formed by the reaction is $\text{R-R}$ and can be formed by the reaction the alkyl halide with organoborane. Step 1 involves formation of organoborane. Step 2 is the reaction of organoborane formed and alkyl halide to give product $\text{hex-1-enylbenzene}$ as shown in Figure 8.

Figure 8

Conclusion

The product formed is rightfully stated.