Carboxylic acids nitriles
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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.

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Carboxylic Acids Nitriles

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Carboxylic AcidsNitriles

Natural Products






Fats and Fatty Acids


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


Ester Formation

Carboxylic Acid Preparations

  • Oxidation of 1o alcohols and aldehydes with Na2Cr2O7/H2SO4

  • KMnO4 oxidation of alkylbenzenes

  • Grignard reaction with CO2 (Carboxylation)

  • Hydrolysis of a carboxylic derivative:

    e.g. acid chloride, acid anhydride, ester, amide, nitrile

Grignard Reaction with CO2


Hydrolysis of a Nitrile

Reduction of Carboxylic Acids

Naming Nitriles

Dehydration of an Amideuse strong dehydrating agent

Reduction of Nitriles

Grignard Addition to a Nitrile

Partial Mechanism

The Rest of the Mechanism

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