Organic Chemistry: Principles and Mechanisms (Second Edition)
Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
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Chapter 12, Problem 12.57P
Interpretation Introduction

Interpretation:

The mechanism for the given Simmons-Smith reaction is to be completed.

Concept introduction:

The Simmons-Smith reaction is an addition of CH2 across the double bond of the alkene to form a cyclopropane ring in the product. The mechanism for this transformation is very similar to that for epoxidation of an alkene by peracids. It involves a concerted action, with the bond making and bond breaking process occurring simultaneously.

Zn-C, C-I and C=C bonds are broken, and simultaneously, new C-C and Zn-I bonds are formed.

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Organic Chemistry: Principles and Mechanisms (Second Edition)

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