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Chapter 13: Carboxylic Acids Back To Chapter

13.7: Preparation of Carboxylic Acids: Overview

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Preparation of Carboxylic Acids: Overview

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13.6: NMR and Mass Spectroscopy of Carboxylic Acids

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Carboxylic acids can be prepared by oxidizing alkenes, alkynes, aldehydes, primary alcohols, or alkylbenzenes.

When alkenes react with hot basic KMnO₄ or, undergo ozonolysis, they yield carboxylic acids.

Similarly, when alkynes are treated with concentrated KMnO₄ or, O₃ followed by H₂O treatment, they undergo oxidative cleavage to form carboxylic acids.

In the case of terminal unsaturation, CO₂ is released along with the acid that is formed.

1° alcohols and aldehydes are oxidized by strong oxidants such as Cr(VI) or Mn(VII) reagents, to generate carboxylic acids. Aldehydes can also be oxidized using mild reagents like Ag₂O .

Aromatic carboxylic acids can be prepared by oxidizing alkylbenzenes, provided at least one benzylic hydrogen is present.

Here, the alkyl group is completely oxidized to give benzoic acid.

Further, the presence of non-oxidizable substituents results in substituted aromatic acids.

Alternatively, alkylbenzenes upon ozonolysis, followed by H₂O₂ treatment, leads to the conversion of the benzene ring to the carboxyl group.

13.7: Preparation of Carboxylic Acids: Overview

There are various methods for the preparation of carboxylic acids. For example, oxidation of primary alcohols or aldehydes using strong oxidizing agents results in a carboxylic acid. Aldehydes can also be oxidized in the presence of mild oxidizing agents.

Alkyl benzenes, bearing at least one benzylic hydrogen, can be oxidized using KMnO₄ or Na₂Cr₂O₇to yield benzoic acid exclusively. The reaction is carried out under vigorous conditions such as heat and high oxidant concentration.

When internal alkynes are treated with concentrated KMnO₄ or, upon ozonolysis, undergo oxidative cleavage to yield carboxylic acids. In comparison, terminal alkynes release CO₂ along with the generation of the acid.

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Preparation Carboxylic Acids Oxidation Primary Alcohols Aldehydes Strong Oxidizing Agents Mild Oxidizing Agents Alkyl Benzenes KMnO4 Na2Cr2O7 Benzoic Acid Vigorous Conditions Heat High Oxidant Concentration Internal Alkynes Concentrated KMnO4 Ozonolysis Oxidative Cleavage Terminal Alkynes CO2

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