ORGANIC CHEMISTRY-WILEYPLUS+ETEXT PKG.
ORGANIC CHEMISTRY-WILEYPLUS+ETEXT PKG.
4th Edition
ISBN: 9781119830269
Author: Klein
Publisher: WILEY
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Chapter 25, Problem 57PP
Interpretation Introduction

Interpretation:

Why there is a difference in yield when alanine and valine is prepared via amidomalonate synthesis need to be explained.

Concept introduction:

Amidomalonate synthesis is a process in which a halide is converted to a aminoacid with two new carbon atoms (comes from amidomalonate).  By use of this method a new alkyl groups can be introduced.  A general scheme of this synthesis is shown below,

ORGANIC CHEMISTRY-WILEYPLUS+ETEXT PKG., Chapter 25, Problem 57PP

Steps involved in amidomalonater synthesis are,

  • Deprotonation of α carbon in amidomalonate
  • Alkylation of enolate
  • Hydrolysis of ester using aqueous acid
  • Decarboxylation at high temperature

Please remember that if the primary alkyl halide reactivity is more than secondary alkyl halide due to less steric hindrance.

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Chapter 25 Solutions

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