Chapter 13.10, Problem 19ATS

Interpretation Introduction

Interpretation: The mechanism for the formation of the diol has to be given and has to indicate the ${}^{\text{18}}\text{O}$ in the diol product.

Concept Introduction:

The reactions of Epoxides with strong nucleophiles requires a strong driving force that helps in the removal of ring strain associated with the three-membered ring of an Epoxide. These ring opening reactions also occur under acidic conditions.

     

When the epoxide is unsymmetrical, the nucleophile attacks at the more substituted position of the protonated epoxide ring.

The mechanism of acid-catalyzed ring opening of an Epoxide occurs in two steps.

In first step, the protonation of Epoxide occurs.

In second step, the attack of nucleophile occurs in the protonated Epoxide by ${\text{S}}_{\text{N}}\text{2}$ process.