Chem262.W11.Lab7-9 - Chemistry 262 Laboratory Experiments...

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Laboratory Experiments 7-9: Multi-step Synthesis For the Weeks of 2/28/11 – 3/18/11 Objectives Carry out several important reactions, including the Knoevenagel condensation, a NaBH 4 reduction, and a Diels-Alder reaction Gain experience carrying out multi-step reactions in the semi-micro and micro scale Gain experience monitoring reactions by TLC Gain experience using physical properties, chemical transformations, and NMR and GC/MS to aid in the identification of compounds Gain experience in how to exercise patience in the context of real synthetic development Tolerate the, whim, fancy, and stubbornness of your instructor Reading  Again review the use of microscale glassware in Zubrick (chapter 5).  Also review the setup for microscale  distillation (page 192) and microscale extraction (pages 142-144).  It is important to understand what you are  Introduction Having taken a little time to regroup, we will now use dimedone for what it was initially intended for –  simple and benign technique to carry out a Knoevenagel condensation between dimedone and benzaldehyde, as  shown below.  This will remove any highly annoying acidic protons and we should be able to carry out our  borohydride reduction.  From there we will follow our initial strategy and heat in acid to from a s-cis diene and  condense it with maleic anhydride to form a Diels-Alder adduct. 1
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This note was uploaded on 07/03/2011 for the course CHEM 121 taught by Professor Matt during the Spring '11 term at Edmonds Community College.

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Chem262.W11.Lab7-9 - Chemistry 262 Laboratory Experiments...

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