Chapter 13, Problem 64IP

Interpretation Introduction

Interpretation: The product of the given reaction to be predicted.

Concept Introduction:

Ring-opening reactions of epoxide:

• Generally, Epoxides have significant ring strain (high in energy), thus it undergoes reaction in which the ring is opened and alleviates the strain. Ring-opening occurs under conditions involving a strong nucleophile or under acid-catalyzed conditions.
• The reaction transformation involves two mechanistic step:

1. 1. I. Nucleophilic attack via ${\text{S}}_{\text{N}}\text{2}$ process.
   2. II. Proton transfer.

• Regiochemistry: if the epoxide is unsymmetrical, the nucleophile attacks at the less hindered position (less substituted).
• Stereochemistry:  when the attack takes place at the chiral center, inversion of configuration is observed. Only the center being attacked undergoes an inversion of configuration.

To Identify: The product of the given reaction to be identified.