Organic Chemistry
Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
Question
Chapter 26, Problem 26.1P
Interpretation Introduction

(a)

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

Concept introduction: Organocuprate reagents (R2CuLi) react with halides of organic compounds, 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.

Expert Solution
Check Mark

Answer to Problem 26.1P

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

Organic Chemistry, Chapter 26, Problem 26.1P , additional homework tip  1

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 C-C bond. The reaction of chlorohexane with the organocuprate reagent results in the formation of octene is shown in Figure 1.

Organic Chemistry, Chapter 26, Problem 26.1P , additional homework tip  2

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 (R2CuLi) react with halides of organic compounds 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.

Expert Solution
Check Mark

Answer to Problem 26.1P

The product of the coupling reaction is 2-methylcyclohexene as shown below.

Organic Chemistry, Chapter 26, Problem 26.1P , additional homework tip  3

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 C-C bond. The reaction of 2-bromocyclohexene with the reagent results in the formation of 2-methylcyclohexene is shown in Figure 2.

Organic Chemistry, Chapter 26, Problem 26.1P , additional homework tip  4

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 (R2CuLi) react with halides of organic compounds 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.

Expert Solution
Check Mark

Answer to Problem 26.1P

The product of the coupling reaction is 4-butyl-1, 2-dimethoxybenzene as shown below.

Organic Chemistry, Chapter 26, Problem 26.1P , additional homework tip  5

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 C-C bond. The reaction of 4-iodo-1, 2-dimethoxybenzene with the reagent results in the formation of 4-butyl-1, 2-dimethoxybenzene as shown in Figure 3.

Organic Chemistry, Chapter 26, Problem 26.1P , additional homework tip  6

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 (R2CuLi) react with halides of organic compounds 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.

Expert Solution
Check Mark

Answer to Problem 26.1P

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

Organic Chemistry, Chapter 26, Problem 26.1P , additional homework tip  7

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 C-C bond. The reaction of (Z)-6-bromo-2-methylocta-2, 6-diene with the reagent results in the formation of (Z)-6-ethylidene-2, 7-dimethylnon-2-ene is shown in Figure 4.

Organic Chemistry, Chapter 26, Problem 26.1P , additional homework tip  8

Figure 4

Conclusion

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

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Chapter 26 Solutions

Organic Chemistry

Ch. 26 - Problem 26.11 What product is formed when each...Ch. 26 - Prob. 26.12PCh. 26 - Problem 26.13 Draw the products formed when each...Ch. 26 - Problem 26.14 What products are formed when ...Ch. 26 - Problem 26.15 Draw the product formed from...Ch. 26 - What product is formed by ring-closing metathesis...Ch. 26 - Problem 26.17 What starting material is needed to...Ch. 26 - 26.18 In addition to organic halides, alkyl...Ch. 26 - 26.19 What product is formed by ring-closing...Ch. 26 - 26.20 Draw the products formed in each...Ch. 26 - What organic halide is needed to convert lithium...Ch. 26 - 26.22 How can you convert ethynylcyclohexane to...Ch. 26 - 26.23 What compound is needed to convert styrene...Ch. 26 - 26.24 What steps are needed to convert to octane...Ch. 26 - Prob. 26.25PCh. 26 - Prob. 26.26PCh. 26 - 26.27 Draw the products (including stereoisomers)...Ch. 26 - 26.28 Treatment of cyclohexene with and forms...Ch. 26 - Prob. 26.29PCh. 26 - 26.30 What starting material is needed to prepare...Ch. 26 - Prob. 26.31PCh. 26 - Prob. 26.32PCh. 26 - When certain cycloalkenes are used in metathesis...Ch. 26 - 26.34 Draw the products formed in each reaction. ...Ch. 26 - Prob. 26.35PCh. 26 - Draw a stepwise mechanism for the following...Ch. 26 - Sulfur ylides, like the phosphorus ylides of...Ch. 26 - Although diazomethane is often not a useful...Ch. 26 - Prob. 26.39PCh. 26 - Prob. 26.40PCh. 26 - Prob. 26.41PCh. 26 - Prob. 26.42PCh. 26 - 26.43 Devise a synthesis of each compound using a...Ch. 26 - 26.44 Devise a synthesis of each compound from...Ch. 26 - 26.45 Devise a synthesis of each compound from...Ch. 26 - 26.46 Devise a synthesis of each substituted...Ch. 26 - Biaryls, compounds containing two aromatic rings...Ch. 26 - Prob. 26.48PCh. 26 - 26.49 Draw the product formed from the...Ch. 26 - Prob. 26.50PCh. 26 - 26.51 Devise a synthesis of each of the following...Ch. 26 - Prob. 26.52PCh. 26 - 26.53 The following conversion, carried out in the...Ch. 26 - Prob. 26.54PCh. 26 - 26.55 Dimethyl cyclopropanes can be prepared by...Ch. 26 - Prob. 26.56P
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