The reaction of ninhydrin with an -amino acid occurs in several steps (a) The first step is loss of water to give a triketone. Show the mechanism of the reaction and the structure of the triketone.

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
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The reaction of ninhydrin with an -amino acid occurs in several steps

(a) The first step is loss of water to give a triketone. Show the mechanism of the reaction and
the structure of the triketone.
(b) The second step is formation of an imine by reaction of the amino acid with the triketone.
Show its structure.
(c) The third step is a decarboxylation. Show the structure of the product and the mechanism
of the decarboxylation reaction.

(d) The fourth step is hydrolysis of an imine to yield an amine and an aldehyde. Show the

structures of both products.

(e) The final step is formation of the purple anion. Show the mechanism of the reaction

 

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