Given that cis- and trans -isomers of 2-butene give different cyclopropane products in the Simmons-Smith reaction. The structures of both the products are to be given and the difference is to be explained. Concept introduction: The reaction given is an example of Simmons-Smith reaction. When CH 2 I 2 is treated with Zn/Cu couple, iodomethylzinc iodide, ICH 2 ZnI, is formed. This ICH 2 ZnI transfers a CH 2 group to the double bond in alkene to form a cyclopropane ring in the product. The reaction occurs with syn stereochemistry. To give: The structures of the products produced when cis- and trans -isomers of 2-butene react in Simmons-Smith reaction and to explain the difference.

Question

Provide the reasonable steps to achieve the following synthesis.

Answer 1

Question

Chapter 8.SE, Problem 47AP

Interpretation Introduction

Interpretation:

Given that cis- and trans-isomers of 2-butene give different cyclopropane products in the Simmons-Smith reaction. The structures of both the products are to be given and the difference is to be explained.

Concept introduction:

The reaction given is an example of Simmons-Smith reaction. When CH₂I₂ is treated with Zn/Cu couple, iodomethylzinc iodide, ICH₂ZnI, is formed. This ICH₂ZnI transfers a CH₂ group to the double bond in alkene to form a cyclopropane ring in the product. The reaction occurs with syn stereochemistry.

To give:

The structures of the products produced when cis- and trans-isomers of 2-butene react in Simmons-Smith reaction and to explain the difference.

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Answer 2

Question

Chapter 8.SE, Problem 47AP

Interpretation Introduction

Interpretation:

Given that cis- and trans-isomers of 2-butene give different cyclopropane products in the Simmons-Smith reaction. The structures of both the products are to be given and the difference is to be explained.

Concept introduction:

The reaction given is an example of Simmons-Smith reaction. When CH₂I₂ is treated with Zn/Cu couple, iodomethylzinc iodide, ICH₂ZnI, is formed. This ICH₂ZnI transfers a CH₂ group to the double bond in alkene to form a cyclopropane ring in the product. The reaction occurs with syn stereochemistry.

To give:

The structures of the products produced when cis- and trans-isomers of 2-butene react in Simmons-Smith reaction and to explain the difference.

Expert Solution & Answer

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Answer 3

Question

Chapter 8.SE, Problem 47AP

Interpretation Introduction

Interpretation:

Given that cis- and trans-isomers of 2-butene give different cyclopropane products in the Simmons-Smith reaction. The structures of both the products are to be given and the difference is to be explained.

Concept introduction:

The reaction given is an example of Simmons-Smith reaction. When CH₂I₂ is treated with Zn/Cu couple, iodomethylzinc iodide, ICH₂ZnI, is formed. This ICH₂ZnI transfers a CH₂ group to the double bond in alkene to form a cyclopropane ring in the product. The reaction occurs with syn stereochemistry.

To give:

The structures of the products produced when cis- and trans-isomers of 2-butene react in Simmons-Smith reaction and to explain the difference.

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Answer 4

Question

Chapter 8.SE, Problem 47AP

Interpretation Introduction

Interpretation:

Given that cis- and trans-isomers of 2-butene give different cyclopropane products in the Simmons-Smith reaction. The structures of both the products are to be given and the difference is to be explained.

Concept introduction:

The reaction given is an example of Simmons-Smith reaction. When CH₂I₂ is treated with Zn/Cu couple, iodomethylzinc iodide, ICH₂ZnI, is formed. This ICH₂ZnI transfers a CH₂ group to the double bond in alkene to form a cyclopropane ring in the product. The reaction occurs with syn stereochemistry.

To give:

The structures of the products produced when cis- and trans-isomers of 2-butene react in Simmons-Smith reaction and to explain the difference.

Expert Solution & Answer

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Answer 5

Chapter 8.SE, Problem 47AP

Interpretation Introduction

Interpretation:

Given that cis- and trans-isomers of 2-butene give different cyclopropane products in the Simmons-Smith reaction. The structures of both the products are to be given and the difference is to be explained.

Concept introduction:

The reaction given is an example of Simmons-Smith reaction. When CH₂I₂ is treated with Zn/Cu couple, iodomethylzinc iodide, ICH₂ZnI, is formed. This ICH₂ZnI transfers a CH₂ group to the double bond in alkene to form a cyclopropane ring in the product. The reaction occurs with syn stereochemistry.

To give:

The structures of the products produced when cis- and trans-isomers of 2-butene react in Simmons-Smith reaction and to explain the difference.

Answer 6

Chapter 8.SE, Problem 47AP

Interpretation Introduction

Interpretation:

Given that cis- and trans-isomers of 2-butene give different cyclopropane products in the Simmons-Smith reaction. The structures of both the products are to be given and the difference is to be explained.

Concept introduction:

The reaction given is an example of Simmons-Smith reaction. When CH₂I₂ is treated with Zn/Cu couple, iodomethylzinc iodide, ICH₂ZnI, is formed. This ICH₂ZnI transfers a CH₂ group to the double bond in alkene to form a cyclopropane ring in the product. The reaction occurs with syn stereochemistry.

To give:

The structures of the products produced when cis- and trans-isomers of 2-butene react in Simmons-Smith reaction and to explain the difference.

Answer 7

Chapter 8.SE, Problem 47AP

Interpretation Introduction

Interpretation:

Given that cis- and trans-isomers of 2-butene give different cyclopropane products in the Simmons-Smith reaction. The structures of both the products are to be given and the difference is to be explained.

Concept introduction:

The reaction given is an example of Simmons-Smith reaction. When CH₂I₂ is treated with Zn/Cu couple, iodomethylzinc iodide, ICH₂ZnI, is formed. This ICH₂ZnI transfers a CH₂ group to the double bond in alkene to form a cyclopropane ring in the product. The reaction occurs with syn stereochemistry.

To give:

The structures of the products produced when cis- and trans-isomers of 2-butene react in Simmons-Smith reaction and to explain the difference.

Answer 8

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Ch. 8.1 - Prob. 1P Ch. 8.1 - How many alkene products, including E,Z isomers,...Ch. 8.2 - Prob. 3P Ch. 8.2 - Addition of HCl to 1, 2-dimethylcyclohexene yields...Ch. 8.3 - Prob. 5P Ch. 8.3 - Prob. 6P Ch. 8.4 - Prob. 7P Ch. 8.4 - From what alkenes might the following alcohols...Ch. 8.5 - Prob. 9P Ch. 8.5 - What alkenes might be used to prepare the...

Chapter 8 Solutions