Chapter 13.12, Problem 23ATS

Interpretation Introduction

Interpretation: The efficient synthesis of the conversion of compound $1$ to compound $2$ has to be determined.

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.

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.

Under acidic condition, attack takes place at more substituted place.

Under basic condition, attack takes place at less substituted place.

PCC [Pyridinium chlorochromate]:

It is a selective oxidizing agent and it well work with secondary alcohols. Secondary alcohol reaction with PCC (oxidizing agent) provides ketone.