carboxylic acid derivatives
Post on 03-Feb-2016
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1
Carboxylic Acid Derivatives
2
Phosphate Nomenclature
3
Nucleophilic Substitution Rxn’s
4
Sterics
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Electronics (polarization)
Sulfer is more polarizable than oxygen, thus a better leaving group
Why acetic anhydride then? Resonance (stabilization of L.G.)
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Isotope Labeling
• How do we really know how these mechanisms work?
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DCC most commonly used for the synthesis of peptides (proteins)
11
LAH reduction forms an alcohol
Aluminum plays an important role in the mechanism
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Sterics Role in Alcoholysis
14
Grignard attack of Acid Chlorides
Will get two additions, can’t control single vs. double addition
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Gilman Reagent – Can Isolate the Ketone
Example:
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Synthesis of Aspirin
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Preparation of Tylenol
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Interesting Ester Examples
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Ester Synthesis
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Base Catalyzed Hydrolysis
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Acid Catalyzed Hydrolysis
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Synthesis of Amides
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Base Catalyzed Hydrolysis
26
What should you expect in Biochemistry?
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LAH reduction of Amides
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Step Growth Polymers
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Biodegradable Polymers
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NMR of Ethyl Acetate
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