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Chem 3BL - Lab Report E#26

Chem 3BL - Lab Report E#26 - Kylie 27 October 2010 Chem 3B...

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Kylie 27 October 2010 Chem 3B Lab Experiment #26: Diels-Alder Reaction Discussion: The TLC results of the ether extract were similar to those of the reaction mixtures (during the heating process), with 3 stains on the lane: the top UV and iodine spot from monoterpene C (Rf=0.7, 0.8), the middle spot from the crude product after NaOH treatment (Rf=0.48, 0.52), and the bottom one from maleic anhydride (Rf=0, 0.06). The lower Rf values belonged to the ether extract stains, suggesting that an increase in polarity had occurred. Since the NaOH- treated product became an anion, it interacted more with the ethyl acetate (60:40 hexane:ethyl acetate solvent) and maybe with the other components as well. The monoterpene (B-myrcene) resulted in UV stains due to some conjugation, and also had light iodine stains surrounding the UV spots (perhaps because its chain makes a 6-membered ring-like formation?). Maleic anhydride, with some conjugation but no aromaticity, was visualized under the UV light only. The NaOH-treated product's stain was visualized in both UV and iodine conditions, since it contains a 6-membered ring and two alkene bonds (more conjugation, darker UV stain).
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