Chapter 23, Problem 23.91P

Interpretation Introduction

Interpretation:

The structure of compounds A-H in the given synthesis is to be determined.

Concept introduction:

The synthesis of monoacylated product is formed in the electrophilic aromatic substitution from acyl chloride and arenes. Here, Friedel-Craft acylation occurs to form the ketone. The ketone is reduced to the isopentyl benzene. The alkyl group is an ortho/para director, and owing to sterics, nitration occurs primarily at the para position. The amine is formed when nitro group is reduced. which is then transformed into the diazonium ion. which reacts with $\text{CuCN}$ to form the nitrile. The nitrile undergoes a Grignard reaction to form the ketone, which is reduced to the secondary alcohol.