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Lab 9 - chalcones_10

Lab 9 - chalcones_10 -...

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Solvent-Free Synthesis of Chalcones Adapted from Daniel R. Palleros, “Solvent-Free Synthesis of Chalcones,”  J. Chem. Ed.,   2004,   81,  1345. During this lab you will be performing an aldol condensation, and also possibly a Michael addition. First,  you need to read the Journal of Chemical Education paper and supplemental material that was uploaded to  blackboard to get an idea of what the lab is about, to obtain a little background on the chemistry of chalcones and  also to learn about the possible side reactions you might expect to see.  Chalcones are organic compounds that can be synthesized in several different ways. We will be using a  solventless system to make chalcones in the lab. Chalcones made in this way are synthesized from an aldehyde  and a ketone. In the presence of a small amount of finely powdered NaOH and a great deal of stirring, they form  chalcones nearly instantly! The scheme below shows the reaction as well as the various substitutions that are on  the aldehyde and the ketone.   H O CH 3 O R1 R2 + NaOH O + H 2 O R 1  =  4-CH 3 , 4-OCH 3 , 4-Cl, -H R 2  =  4-CH 3 , 4-Br, 4-OCH 3 , -H If   we   used   all   of   the   possible   combinations   of   starting   materials   shown   above   as   well   as   3- Chlorobenzaldehyde, we could make 20 different chalcones. The authors of this paper, as well as the Organic Lab  Class of 2009, however, have found that a few of the combinations using that aldehyde gave a low yield or an  amorphous product. To that end, we will not be making those.  Each of you will have a chalcone combination assigned to you based on the number in the attached table.  That assignment sheet is uploaded in Blackboard. Say for example, you are assigned Chalcone #4. You will use  Acetophenone as your ketone and 4-Methylbenzaldehyde as your aldehyde to synthesize your compound. The 
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table in the supplemental information from the article not only contains information on which compounds you  should use to make the product, it also includes experimental data already determined for the compounds. The 
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