Research Publication Title

Development of an Organic Laboratory Experiment: An Old School Characterization of Ketones and Aldehydes

Presenter Information

Joseph A. ClelandFollow

Major

Chemistry and Biology

Faculty Mentor(s)

Dr. Kimberly Cossey Dr. Ronald Fietkau

Keywords

Organic chemistry, education, 2, 4-dinitrophenylhydrazine, nucleophilic substitution, oxidation

Abstract

The purpose of this research is to develop an organic chemistry lab that compares methods of characterizing ketones and aldehydes, while completing nucleophilic substitution and oxidation reactions. In the past, qualitative tests were used to verify the structures of organic molecules. While spectroscopy has all but replaced these methods, students can learn valuable reaction chemistry using classic reagents. Students will characterize products of a reaction using 2,4-dinitrophenylhydrazine to replace the carbonyl group via a nucleophilic substitution and the silver mirror test to further oxidize the product. They will then analyze the products using NMR. These characterization reactions will be coupled to a green oxidation reaction of alcohols to form the desired carbonyls. A range of primary and secondary alcohols will be oxidized to give both ketones and aldehydes. Tertiary alcohols will be used to show both the inability to oxidize a tertiary alcohol and as a negative for the qualitative tests.

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Development of an Organic Laboratory Experiment: An Old School Characterization of Ketones and Aldehydes

The purpose of this research is to develop an organic chemistry lab that compares methods of characterizing ketones and aldehydes, while completing nucleophilic substitution and oxidation reactions. In the past, qualitative tests were used to verify the structures of organic molecules. While spectroscopy has all but replaced these methods, students can learn valuable reaction chemistry using classic reagents. Students will characterize products of a reaction using 2,4-dinitrophenylhydrazine to replace the carbonyl group via a nucleophilic substitution and the silver mirror test to further oxidize the product. They will then analyze the products using NMR. These characterization reactions will be coupled to a green oxidation reaction of alcohols to form the desired carbonyls. A range of primary and secondary alcohols will be oxidized to give both ketones and aldehydes. Tertiary alcohols will be used to show both the inability to oxidize a tertiary alcohol and as a negative for the qualitative tests.