Get Lecture Problem 6

1
Lecture 16

• Get Lecture Problem 6
• The Synthetics

• This Week in Lab
• Ch 9 PreLab Due
• Quiz 5
• Ch 6 Final Report Due
• Next Week
• Spring Break!!!

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The Condensation Reactions
Experiment 14 Synthesis of 3-Carbethoxycoumarin
Go over mechanisms for transesterifcation aldol
condensation in class
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The Condensation Reactions
Experiment 16 Synthesis of Creatine
Go over mechanism in class.
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Esterification

Synthesis of esters
A Typical Esterification (generic example)

• reaction of a carboxylic acid (elec) with an
  alcohol (nuc)
• acid catalyzed
• reversible
• known as a Fisher Esterification

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Esterification
Experiment 80 Synthesis of Aspirin

• Reaction of an alcohol (nuc) with an anhydride
  (elec)
• Similar mechanism to Fisher esterification
• Analyses IR NMR
• Aspirin
• Anti-inflammatory
• analgesic (pain killer)
• Antipyretic (fever reducer)

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More Esterifications
Experiment 86 Synthesis of Benzocaine


Benzocaine

• Fisher esterification reaction
• Analyses IR, NMR MS
• Benzocaine
• Topical local anesthetic for itching and pain
  caused by sunburn, insect
• bites, poison ivy, poison oak, minor cuts
• Deadens the nerve endings in the skin

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Fragrant Esters
Analyses IR, NMR, GC, GC-MS, MS