Get Lecture Problem 5 Due

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! Well 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