Chapter 10, Problem 10.56P

Interpretation Introduction

Interpretation:

The product of the reaction is to be predicted and the complete, detailed mechanism is to be drawn.

Concept introduction:

Epoxides react readily under neutral, basic, and acidic reaction conditions. The mechanism for the epoxides under neutral and basic conditions consists of an ${\text{S}}_{\text{N}}\text{2}$ step followed by a proton transfer reaction. Thus, epoxides can undergo ${\text{S}}_{\text{N}}\text{2}$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides (${\text{R-HN}}^{-}$). Under neutral or basic conditions, a nucleophile attacks an epoxide at the less substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom.