1

Carboxylic Acid Derivatives

2

Phosphate Nomenclature

3

Nucleophilic Substitution Rxn’s

4

Sterics

5

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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10

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

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Grignard attack of Acid Chlorides

Will get two additions, can’t control single vs. double addition

15

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

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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