Transcript Document

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
• 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
The Condensation Reactions
Experiment 12: Thiamine-catalyzed benzoin condensation
O
O
2
CNH
Benzaldehyde
or thiamine
OH
Benzoin
• 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
The Condensation Reactions
Experiment 14: Synthesis of 3-Carbethoxycoumarin
O
8
7
6 5
12
3
4
O
Coumarin, the
parent heterocycle:
a flavoring
O
O
O
O
O
OC 2H 5
3-Carbethoxycoumarin:
your synthetic goal
OH
O
Warfarin:
a rat poison
• 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
The Condensation Reactions
Experiment 15: Synthesis of Dilantin
O
O
+
O
NH2
NH2
H
N
1. NaOH
2. HCl
NH
O
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
O
+
H2O
The Condensation Reactions
Experiment 16: Synthesis of Creatine
H2N C N
+
H
N
O
OH
NaCl
NH4OH
NH
H2N
O
N
H2O
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
OH