Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 24, Problem 3PP
Interpretation Introduction

Interpretation:

The synthesize of DL-leucine, DL-alanine, and DL-phenylalanine from potassium phthalimide and diethyl αa-bromomalonate.

Concept Introduction:

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Amino acids are synthesized by plants and animals. There are some amino acids which are not synthesized by the higher animals. These amino acids are then taken up by the animals from various other sources.

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There are two types of amino acid-syntheses, which are, from potassium phthalimide, and the Strecker synthesis. The potassium phthalimide type of synthesis uses diethyl αa-bromomalonate and SN2 reactions, and hydrolysis and decarboxylation occur in it.

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The potassium phthalimide method is a modification of the Gabriel synthesis of amines. This method uses potassium phthalimide and diethyl a-bromomalonate to prepare an imido malonic ester.

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Decarboxylation reaction is the reaction in which there is loss of a molecule of carbon dioxide from a compound.

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The reaction of an aldehyde with ammonia and hydrogen cyanide produces an αa-aminonitrile, which on hydrolysis, gives amino acid. This synthetic strategy is called the Strecker synthesis.

Organic Chemistry, Chapter 24, Problem 3PP

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