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.