ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG(LL)
ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG(LL)
4th Edition
ISBN: 9781119659587
Author: Klein
Publisher: WILEY
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Chapter 25, Problem 89IP
Interpretation Introduction

Interpretation:

Alkyl halide required for preparation of tyrosine via amidomalonate synthesis and the polymeric material formed from the alkyl halide need to be identified.

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-STUD.SOLNS.MAN+SG(LL), Chapter 25, Problem 89IP

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

Polymerization can occur when an nucleophilic center and an electrophilic center is present in the compound.  These centers if present in the same compound a polymer can be formed.

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ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG(LL)

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