2311 lec 3 - Thalidomide D-isomer morning sickness/sedative...

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Banana Oil Experiment • Flavors and Fragrances • Reflux – New • “Old” – extraction, drying, distillation, bpt • Submit NMR and obtain IR
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Esters – Flavors and Fragrances • Flavor – “combination of taste, sensation, and odor transmitted from receptors in the mouth (taste buds) and nose (olfactory receptors) • Sweet, Sour, Salty, Bitter – but not so simple • 9,000 taste buds
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Structures of Ester Flavors O C O H 3 C CH 2 CH 2 CH CH 3 CH 3 Banana Oil O C O H 3 C O C O H 3 C CH 2 CH 2 CH 3 O C O H 3 C CH 2 CH 2 CH C CH 3 CH 3 Juicy Fruit Pear (CH 2 ) 6 CH 3 Oranges
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Sterochemical Theory of Odor Small structure variations Î Big Physilogical Reponse • Carvones O CH 3 H O CH 3 H (R)-(-)-Carvone from spearmint oil (S)-(+)-Carvone from caraway oil
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Sterochemical Theory of Odor Small structure variations Î Big Physilogical Reponse
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Unformatted text preview: Thalidomide D-isomer morning sickness/sedative L-isomer Teratogen Birth defects N H O O N O O Synthesis of Banana oil Reaction Scheme O OH + OH O O Acetic acid Isopentyl alcohol Isopentyl acetate + H 2 SO 4 H 2 O Fischer Esterification Reaction Equilibrium Control of Equilibrium in the lab Use excess of a reagent (cheapest) Add heat to change equilibrium constant (Remove water) Small scale molecular sieves Large scale Dean Stark trap Reflux Apparatus Banana Oil Experiment R e f l u x Extraction careful with the NaHCO3 D r y C a C l 2 O K Distill to clear, colorless liquid Simple Distillation...
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2311 lec 3 - Thalidomide D-isomer morning sickness/sedative...

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