Chapter 20, Problem 20.62P

Interpretation Introduction

Interpretation:

The missing compounds A through G are to be supplied.

Concept introduction:

$\text{Diisobutylaluminium hydride}$ (DIBAH), a specialized reducing agent, reduces an ester to an aldehyde. Thus, A is produced by reducing the starting material to the aldehyde. Under the basic conditions, A reacts with a ketone B in an aldol condensation reaction. $\text{Lithium dialkylcuprate}$ then undergoes a conjugate addition. This is followed by reduction with ${\text{NaBH}}_4$ to produce D. ${\text{PBr}}_{\text{3}}$ then converts the $\text{-OH}$ group to $\text{Br}$ to produce E. The next reaction is Gabriel synthesis. Gabriel synthesis produces a primary amine from a corresponding alkyl halide. Therefore, in the Gabriel synthesis involving E, the primary amine F is produced. F undergoes Hoffman elimination in the final step to produce G.