Carboxylic Acid Derivatives Acid Chlorides Acid Anhydrides Esters Amides Nitriles Nucleophilic Acyl Substitution.

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Presentation transcript:

Carboxylic Acid Derivatives Acid Chlorides Acid Anhydrides Esters Amides Nitriles Nucleophilic Acyl Substitution

Reactivity of Acid Derivatives

Nucleophilic Acyl Substitution

I.U.P.A.C. Nomenclature ( uses carboxylic acid template)

Acid Chlorides

Acid Anhydrides

Esters

Amides

Lactones (cyclic esters)

Gamma Hydroxybutyrate

All Acid Derivatives can be Hydrolyzed

What are the 3 Hydrolysis Products?

Draw the Hydrolysis Products

Hydrolysis of Penicillin

Aspartame

Hydrolysis of an Acid Chloride

Acid Chloride Preparation

Nucleophilic Acyl Substitution

With Acid Chlorides, No Catalyst is Needed Anhydride Prep.

Ester Preparation from an acid chloride

Amide Preparation from an Acid Chloride

Amide from Anhydride

Fischer Esterification

Fischer Esterification Shows Oxygen “Scrambling” a methanolysis

Diazomethane Preparation of Methyl Esters

Diazomethane has a Basic Carbon

Mechanism

Flavors and Fragrances

Intramolecular Fischer Esterification - GHB

Lactam (cyclic amide) Formation

 -Lactams as Antibiotics

Acid Catalyzed “Olysis” Reactions

Transesterification a Methanolysis

Aspirin Synthesis

Basic Hydrolysis Saponification

Basic Hydrolysis of an Amide

Mechanism

Reduction of Esters with LiAlH 4

DIBAH Diisobutyl Aluminum Hydride

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