Chapter 12, Problem 12.17P

Interpretation Introduction

Interpretation:

The complete, detailed mechanism and the major product, paying close attention to stereochemistry is to be drawn for the given reaction.

Concept introduction:

It is an electrophilic addition reaction of the peroxy group to an alkene. MCPBA contains the ‘peroxy’ $\left(\text{-COOOH}\right)$ group, which acts as an electrophile. Alkene act as a nucleophile and forms an epoxide (oxirane ring) in a concerted first step of the reaction. Rearrangement and rotation about the carbon-carbon double bond in an alkene are not permitted. So, the transfer of oxygen is the same side of the double bond. Therefore, stereochemistry about the carbon-carbon double bond is the same in the product.