C2510_Chalcone_S_2009 - Chemistry 2510 Introduction to...

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Chemistry 2510 Introduction to Experimental Organic Chemistry Spring 2009 Experiment #11 Solvent-Free Synthesis of Chalcones Laboratory Notebook : You need to summarize your experimental plan in your lab notebook. Be sure to include a table of all reagents and compounds that will be used in this experiment. Laboratory Observations: Be sure to record any observations during the laboratory. You must record exactly how much of the starting materials you started with and the weight of the isolated product. Results and Conclusions : Perform a solvent-free reaction using an unknown benzaldehyde and acetophenone derivatives and identify the resulting chalcone product. A determionation of yield and purity will also be done. Relevant Reading: Technique 2, Melting Points, pp 39-48, and Technique 15, IR Spectroscopy, pp 163- 178. Background: One of the principles of “green” chemistry is the use of safer solvents and auxiliaries, or their elimination altogether, whenever possible. This lab will explore the synthesis of chalcones in a solvent-free system in order to aid in reaction and reduce expensive and unnecessary use of hazardous solvents which then must be disposed of. This lab will involve the solvent-free preparation of chalcones. Chalcones are α , β unsaturated ketones possessing aromatic R groups. The chalcones, as a class of compounds, have shown an array of pharmacological activities, such as anti-protozoal, anti-inflammatory, immunomodulatory, nitric oxide inhibition, inhibition of the production of interleukin-1 and anti-cancer activities. Chalcones are most easily prepared via an aldol condensation between an aromatic aldehyde and an aliphatic/aromatic ketone. The reaction is base- ctalyzed and is shown below:
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O H + O CH 3 R 1 R 2 NaOH O R 1 R 2 + H 2 O Chalcone R 1 = 4-CH
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This note was uploaded on 09/08/2009 for the course CHEM 2510 taught by Professor Russo,s during the Spring '07 term at Cornell.

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C2510_Chalcone_S_2009 - Chemistry 2510 Introduction to...

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