Chapter 9, Problem 9.73P

Interpretation Introduction

Interpretation: A stepwise synthesis of propranolol from the given starting materials is to be stated.

Concept introduction: Alcohols react with $\text{NaH}$ and form alkoxide salts. An alkoxide salt contains strong nucleophile $\left({}^{-}\text{OR}\right)$. The nucleophilic attack of ${}^{-}{\text{NH}}_{\text{2}}$ on the electron deficient carbon atom of epichlorohydrin and the nucleophilic attack of ${}^{-}\text{OR}$ on the less substituted carbon of epoxide follow ${\text{S}}_{\text{N}}\text{2}$ pathway.