Chapter 12, Problem 12.19P

Interpretation Introduction

Interpretation:

The missing compounds (products) for the given reaction sequence from A to C are to be identified.

Concept introduction:

Alcohols, when heated with a strong acid, undergo an $\text{E1}$ elimination reaction to yield alkene. Heat favors elimination over substitution. The alkene that has been formed, as a result of the above reaction, is converted to an epoxide using the reagent MCPBA (peroxyacid). It is an electrophilic addition reaction of the peroxy group to an alkene. MCPBA contains the ‘peroxy’ $\left(\text{-COOOH}\right)$ group, which acts as an electrophile and alkene acts as a nucleophile.

Epoxides undergo ${\text{S}}_{\text{N}}\text{2}$, a type of reaction with strong nucleophiles, such as ${\text{HO}}^{\text{-}}$. As the reaction is ${\text{S}}_{\text{N}}\text{2}$, inversion of the configuration is observed in the substituted product. If chiral products are produced, then a mixture of stereoisomers is produced as a final product.