Chapter 12, Problem 12.18P

Interpretation Introduction

Interpretation:

The reactant which can be epoxidized using MCPBA to get the given compound is to be determined.

Concept introduction:

MCPBA contains a peroxycarboxylic acid $\left(\text{-COOOH}\right)$ group, which acts as an electrophile. The oxygen atom from this group simultaneously forms bonds to both carbon atoms of the alkene double bond to form an epoxide (oxirane) ring. The $\text{π}$ electron pair from the double bond forms one bond, while one of the lone pairs of the oxygen atom forms the other bond. The result is a replacement of the $\text{π}$ bond with two $\text{σ}$ bonds.

The cis-trans stereochemistry about the carbon-carbon double bond is retained in the reaction.