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Lecture 15

Lecture 15. Get Lecture Problem 5 Due The Synthetics. This Week in Lab: Ch 9 PreLab Due Quiz 5 Ch 6 Final Report Due Next Week: Spring Break!!!. Chapter 10: Synthetic & Isolation Experiments. 22 different experiments Quick review of experiments

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Lecture 15

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  1. Lecture 15 • Get Lecture Problem 5 Due • The Synthetics • This Week in Lab: • Ch 9 PreLab Due • Quiz 5 • Ch 6 Final Report Due • Next Week: • Spring Break!!!

  2. Chapter 10: Synthetic & Isolation Experiments • 22 different experiments • Quick review of experiments • Designed to show relevance of organic chemistry • Complete 2 of these 22 • You will choose the 2! We’ll do this the Tuesday after Spring Break. • Perform at least one type of analysis, including TLC (for most), for • each experiment. Ideally, different analyses for the 2 you pick. • 5 main types of experiments: condensation, esterification, isolation, • reduction, and substitution

  3. The Condensation Reactions Experiment 12: Thiamine-catalyzed benzoin condensation • Condensation can be catalyzed by cyanide ion or thiamine • Breslow discovered that thiamine hydrochloride, vitamin B1 (in the form • of coenzyme thiamine pyrophosphate, can catalyze this reaction • Vitamin B1 is needed in the diet to prevent beriberi, a nervous system • disease • Reaction mechanism given in class • Analyses include: IR, NMR, UV/Vis, and MS

  4. The Condensation Reactions Experiment 14: Synthesis of 3-Carbethoxycoumarin • Coumarin: blood-thinning, anti-fungicidal, and anti-tumor acitivities; • Responsible for the sweet smell of newly mown hay • Two step synthesis: transesterification and aldol condensation • Reactions shown in class. • Analyses include: IR & NMR

  5. The Condensation Reactions Experiment 15: Synthesis of Dilantin • Facts about dilantin (a.k.a. phenytoin): • Discovered in 1838 • Used as an anticonvulsant for the treatment of epilepsy • Used as an antidepressant • Analyses include: IR & NMR

  6. The Condensation Reactions Experiment 16: Synthesis of Creatine • Facts about creatine: • Produced by the liver, kidney, and pancreas • Made by arginine, glycine, and methionine • Can be absorbed from food - meat and fish particularly • Provides energy for vigorous muscle contraction • May enhance performance in high-intensity exercise • Mechanism shown in class • Analyses include: IR & NMR

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