Carboxylic Acids Nitriles Natural Products Nomenclature Acidity Preparation Reactions.

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Presentation transcript:

Carboxylic Acids Nitriles 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

Ester Formation

Carboxylic Acid Preparations Oxidation of 1 o alcohols and aldehydes with Na 2 Cr 2 O 7 /H 2 SO 4 KMnO 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

Naming Nitriles

Dehydration of an Amide use strong dehydrating agent

Reduction of Nitriles

Grignard Addition to a Nitrile

Partial Mechanism

The Rest of the Mechanism

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