Natural Products Nomenclature Acidity Preparation Reactions Carboxylic Acids Natural Products Nomenclature Acidity Preparation Reactions

Analgesics

Fats and Fatty Acids

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 1o alcohols and aldehydes with Na2Cr2O7/H2SO4 KMnO4 oxidation of alkylbenzenes Hydrolysis of a carboxylic derivative: e.g. acid chloride, acid anhydride, ester, amide, nitrile

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

Reactivity of Acid Derivatives

Acid Chloride Preparation

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

Acid Chlorides

Acid Anhydrides

Esters

Amides

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

With Acid Chlorides, No Catalyst is Needed Anhydride Prep.

Ester Preparation from an acid chloride

Amide Preparation from an Acid Chloride

Amide from Anhydride

Proteins are amides!

Fischer Esterification

Flavors and Fragrances

Basic Hydrolysis Saponification

Basic Hydrolysis of an Amide

Mechanism

Reduction of Esters with LiAlH4

Due 15Mar 5 pm @RAM pigeonbox 10.33 a, d 10.39 10.41 10.44