Chapter 22, Problem 84IP

Interpretation Introduction

Interpretation: A synthesis of phenacetin starting from benzene has to be found

Concept Introduction:

Electrophilic aromatic substitution: Electrophilic aromatic substitution is a reaction in which the hydrogen atom of an aromatic ring is replaced as a result of an electrophilic attack on the aromatic ring.  There are three general steps involved in an electrophilic aromatic substitution.

Williamson ether synthesis: The Williamson ether synthesis is a reaction that converts alcohols (R−OH) into ethers (R−O−R). The first step in this reaction is forming the conjugate base of the alcohol (called an alkoxide) by reacting the alcohol with sodium metal. This reaction forms hydrogen gas (H₂) as a bi-product.

The alkoxide can then be added to a suitable alkyl halide (typically a primary halide) to form the ether via an S_N2 mechanism.

To find: Give a synthesis of phenacetin starting from benzene

Apply a retrosynthetic analysis