Guilford Techno Consultants, Inc

Thursday, December 28, 2023 by Guilford Techno Consultants, Inc. | Name Reactions

A large portion of the second semester of Organic Chemistry is spent learning about carbonyl chemistry which includes the reactions and mechanisms of aldehydes and ketones, carboxylic acids and their derivatives, as well as alpha carbon chemistry. The volume of material can seem a bit daunting. The situation isn’t helped by the fact that many of the reactions appear similar to each other. However overwhelming the material may appear to be, it plays a critical role in Biochemistry, in which carbonyl chemistry figures prominently in many processes.  

The Strecker Amino Acid Synthesis, also known as the Strecker Synthesis, was discovered by Adolph Strecker. It can be used to convert an aldehyde to an alpha-amino acid:

In the first step of the synthesis, an aldehyde is converted to an iminium cation through reaction with ammonium chloride. Subsequent addition of cyanide anion to the iminium ion results in formation of an alpha-amino nitrile. Acid catalyzed hydrolysis of the nitrile group produces an alpha-amino acid. The Strecker Synthesis involves three important mechanisms of Organic Chemistry II: (1) Formation of an imine in the form of an iminium cation, (2) Addition of a cyanide anion to a carbon-nitrogen double bond (similar to cyanohydrin formation), and (3) Acid catalyzed hydrolysis of a nitrile. A mechanism for the Strecker Synthesis can be found in the following presentation. 

Click Here for the Strecker Amino Acid Synthesis