There is a lack of pictorial evidence of the outcome of most reactions in core organic chemistry. This places visual learners at a disadvantage. This presentation supplies visual evidence for the reactions of ethyl acetoacetate and malonic acid. We demonstrate that malonic acid undergoes decarboxylation by detection of carbon dioxide using limewater. The formation of methyl ketones from alkylation and decarboxylation of ethyl acetoacetate is confirmed by the observation of precipitated sodium halides during alkylation and detection of carbon dioxide using lime water. Methyl ketone formation is confirmed by distillating the product onto tubes containing 2,4-dinitrophenylhydrazine (DNP), Jones' reagent and Schiff's reagent. Formation of a yellow precipitate with DNP confirms that a carbonyl is formed. A subsequent positive iodoform test confirms the methyl ketone. Finally, selective reduction of the ketone of ethyl acetoacetate using sodium borohydride is confirmed by color changes from reaction with ceric ammonium nitrate and Jones reagent.

Development of photographically friendly reactions of ethyl acetoacetate and diethyl malonate

243rd National Meeting (2012)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.