Chapter 26.4, Problem 8P

Interpretation Introduction

Interpretation:

The steps in the synthesis of valine from diethyl acetamidomalonate are to be outlined. A reason for the low yield of about $31\%$ for this method is to be given.

Concept Introduction:

The hydrogen bonded to the carbon between the two ester groups of diethylmalonate is acidic because of the adjacent electron withdrawing groups.

Deprotonation with a strong base such as an alkoxide generates a carbanion which can act as a nucleophile.