ORGANIC CHEMISTRY-W/STUD.SOLN.MAN.
ORGANIC CHEMISTRY-W/STUD.SOLN.MAN.
10th Edition
ISBN: 9781260001099
Author: Carey
Publisher: MCG
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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.

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