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					                      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
                                   CN-
                           H
            2                  or thiamine
                                                  OH

                Benzaldehyde                 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      O              O      O           O      O
              8      12
            7
            6 5        3                             O
                     4


           Coumarin, the                        OC 2H 5      OH          O
          parent heterocycle:   3-Carbethoxycoumarin:     Warfarin:
             a flavoring          your synthetic goal     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                          H
                                    1. NaOH          N
                +                                             O   +   H2O
                    NH2       NH2    2. HCl
          O                                              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
                  The Condensation Reactions

Experiment 16: Synthesis of Creatine

                        O         NaCl         H2N       NH
                    H                                         O
  H2N C N     +     N             NH4OH
                            OH                       N
                                   H2O                            OH
                                                     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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