ORGANIC CHEMISTRY,SOLN.MAN.+...-ACCESS
ORGANIC CHEMISTRY,SOLN.MAN.+...-ACCESS
4th Edition
ISBN: 9781119659471
Author: Klein
Publisher: WILEY
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Chapter 25.3, Problem 2LTS
Interpretation Introduction

Interpretation:

Racemic tryptophan prepared by using amidomalonate synthesis need to be shown.

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,SOLN.MAN.+...-ACCESS, Chapter 25.3, Problem 2LTS

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

To describe: how tryptophan can be synthesized using amidomalonate synthesis.

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Please answer 1, 2 and 3 on the end
In the box below, specify which of the given compounds are very soluble in polar aprotic solvents. You may select more than one compound. Choose one or more: NaCl NH4Cl CH3CH2CH2CH2CH2CN CH3CH2OH hexan-2-one NaOH CH3SCH3
On the following structure, select all of the atoms that could ACCEPT a hydrogen bond. Ignore possible complications of aromaticity. When selecting be sure to click on the center of the atom.

Chapter 25 Solutions

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