Devise a synthesis of each amino acid from acetaldehyde (CH3CHO): (a) alanine

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter26: Biomolecules: Amino Acids, Peptides, And Proteins
Section26.SE: Something Extra
Problem 37AP
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Devise a synthesis of each amino acid from acetaldehyde (CH3CHO):

(a) alanine

Expert Solution
Step 1

Strecker synthesis is method used for the preparation of amino acid from aldehyde. In this synthesis, firstly the aldehyde is treated with NH3 and HCN to form aminonitrile. Aminonitrile is then treated with HCl and H2O to form the required amino acid.

 

Step 2

In the synthesis of alanine, firstly acetaldehyde is reacted with NH3 and HCN to prepare aminonitrile. NH3 attacks on the carbonyl carbon of acetaldehyde to form the intermediate species. CN- attacks on the carbon atom bonded to nitrogen to form aminonitrile.

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