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

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 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


Mechanism


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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