Carboxylic Acids Natural Products Nomenclature Acidity Preparation Reactions
Carboxylic Acids Natural Products Nomenclature Acidity Preparation Reactions
Analgesics
Fats and Fatty Acids
Prostaglandins
Penicillins from mold
From Ergot Fungus
Common Nomenclature
I. U. P. A. C. Nomenclature
Dicarboxylic Acids
A Diacid
Unusually High Melting and Boiling Points
Boiling Points
Acidity is due to Delocalization of the Charge in the Conjugate Base
Alcohol vs. Acid
e Withdrawing Groups Enhance Acidity
Benzoic acids
Deprotonation
Carboxylic Acid Preparations • Oxidation of 1 o alcohols and aldehydes with Na 2 Cr 2 O 7/H 2 SO 4 • KMn. O 4 oxidation of alkylbenzenes • Grignard reaction with CO 2 (Carboxylation) • Hydrolysis of a carboxylic derivative: e. g. acid chloride, acid anhydride, ester, amide, nitrile
Grignard Reaction with CO 2
Mechanism
Hydrolysis of a Nitrile
Reduction of Carboxylic Acids
Carboxylic Acid Derivatives Acid Chlorides Acid Anhydrides Esters Amides Nitriles Nucleophilic Acyl Substitution
Reactivity of Acid Derivatives
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
Nucleophilic Acyl Substitution
Nucleophilic Acyl Substitution
Hydrolysis of an Acid Chloride
Acid Chloride Preparation
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
Flavors and Fragrances
Intramolecular Fischer Esterification - GHB
Lactam (cyclic amide) Formation
b-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 Li. Al. H 4
DIBAH Diisobutyl Aluminum Hydride
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