Chapter 20, Problem 20.64P

Interpretation Introduction

Interpretation:

The missing compounds A through G are to be supplied.

Concept introduction:

The starting alkene undergoes hydroboration-oxidation to form the primery alcohol A. The alcohol is oxidized to the carboxylic acid B by ${\text{KMnO}}_{\text{4}}$, followed by acid work up. The carboxylic acid reacts with ${\text{CH}}_{\text{2}}{\text{N}}_{\text{2}}$ to form the methyl ester C. The ester undergoes addition of two ${\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{}^{\text{-}}$ nucleophiles by a Grignard reaction to form tertiary alcohol D. This alcohol undergoes a dehydration reaction to form risubstituted alkene. The alkene then undergoes hydroboration-oxidation to form the less substituted alcohol F. The alcohol is deprotonated by NaH to form an ${\text{O}}^{\text{-}}$ nucleophile that reacts with ester C to form the new ester G.