Organic Chemistry
Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 24, Problem 4PP
Interpretation Introduction

Interpretation:

The Strecker synthesis of DL-phenylalanine is to be outlined, and by preparing the starting aldehyde using acrolein and methanethiol, Strecker synthesis of DL-methanethiol is to be outlined.

Concept introduction:

舧 Amino acids are organic compounds containing amine (NH2) and carboxyl (COOH) functional group along with a side chain (R group) specific to each amino acid.

舧 Strecker synthesis involves treating an aldehyde with ammonia and hydrogen cyanide to give an aminonitrile, which can be hydrolyzed to an αa-amino acid.

The general reaction is as:

Organic Chemistry, Chapter 24, Problem 4PP

舧 The Strecker synthesis involves formation of imine from phenyl acetaldehyde and ammonia, which on addition of hydrogen cyanide produces α amino nitrile, and further undergoes hydrolysis to yield DL-phenylalanine.

舧 Acrolein and methanethiol on treating with a base gives 3(methylthio)propanal, which when subjected to Strecker synthesis forms imine from 3(methylthio)propanal and ammonia, which on addition of hydrogen cyanide produces α amino nitrile, and further undergoes hydrolysis in the second step to yield DL-Methionine.

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