Core - Organic Chemistry

Chapter 13

Carboxylic Acids

13.1 : IUPAC Nomenclature of Carboxylic Acids

13.1 : IUPAC Nomenclature of Carboxylic Acids

IUPAC names of carboxylic acids are systematically derived following a few rules discussed below. For acyclic saturated monocarboxylic acids, the longest ...

13.2 : Physical Properties of Carboxylic Acids

13.2 : Physical Properties of Carboxylic Acids

Carboxylic acids with lower molecular weight exhibit a sharp and unpleasant odor. They also have higher boiling and melting points than analogous ...

13.3 : Acidity of Carboxylic Acids

13.3 : Acidity of Carboxylic Acids

Carboxylic acids are the strongest organic acids. However, their acidic strength is much less than mineral acids like HCl. Carboxylic acids ionize in ...

13.4 : Substituent Effects on Acidity of Carboxylic Acids

13.4 : Substituent Effects on Acidity of Carboxylic Acids

The acidity of carboxylic acids is influenced by the nature of the substituents bounded to the functional group. The acid strength is determined by the ...

13.5 : IR and UV–Vis Spectroscopy of Carboxylic Acids

13.5 : IR and UV–Vis Spectroscopy of Carboxylic Acids

In IR spectroscopy of carboxylic acids, the C=O bond shows a characteristic band between 1710 and 1760 cm⁻¹, and the O–H bond exhibits a ...

13.6 : NMR and Mass Spectroscopy of Carboxylic Acids

13.6 : NMR and Mass Spectroscopy of Carboxylic Acids

In ¹H NMR spectroscopy, acidic protons (–COOH) of carboxylic acids are highly deshielded and absorb far downfield, at around 9–12 ppm. ...

13.7 : Preparation of Carboxylic Acids: Overview

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 ...

13.8 : Preparation of Carboxylic Acids: Hydrolysis of Nitriles

13.8 : Preparation of Carboxylic Acids: Hydrolysis of Nitriles

Nitriles (R–CN) can be converted into carboxylic acids (R–COOH) upon treatment with aqueous acids, i.e., upon hydrolysis of nitriles. Under ...

13.9 : Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents

13.9 : Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents

Carboxylic acids can be prepared by the carboxylation of Grignard reagents (RMgX). This method is convenient for converting alkyl (primary, secondary ...

13.10 : Reactions of Carboxylic Acids: Introduction

13.10 : Reactions of Carboxylic Acids: Introduction

Carboxylic acids possess an acidic –COOH functional group. The acidity can be attributed to the resonance stabilization of their conjugate ...

13.11 : Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview

13.11 : Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview

The Fischer esterification reaction was developed by the German chemist Emil Fischer in 1895. It is a condensation reaction between carboxylic acids ...

13.12 : Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism

13.12 : Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism

Carboxylic acids react with alcohols to yield esters via an acid-catalyzed condensation reaction called Fischer esterification. This is a ...

13.13 : Carboxylic Acids to Methylesters: Alkylation using Diazomethane

13.13 : Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the ...

13.14 : Carboxylic Acids to Acid Chlorides

13.14 : Carboxylic Acids to Acid Chlorides

Carboxylic acids react with SOCl2 or PCl5 to form acid chlorides. Amongst the carboxylic acid derivatives, acid chlorides are the most reactive and ...

13.15 : Carboxylic Acids to Primary Alcohols: Hydride Reduction

13.15 : Carboxylic Acids to Primary Alcohols: Hydride Reduction

Carboxylic acids, upon reaction with strong reducing agents such as lithium aluminum hydride followed by hydrolysis, undergo reduction to form primary ...

13.16 : Loss of Carboxy Group as CO<sub>2</sub>: Decarboxylation of β-Ketoacids

13.16 : Loss of Carboxy Group as CO₂: Decarboxylation of β-Ketoacids

Carboxylic acids, upon heating, undergo a decarboxylation reaction by releasing carbon dioxide gas. Monocarboxylic acids do not undergo decarboxylation ...

13.17 : Loss of Carboxy Group as CO<sub>2</sub>: Decarboxylation of Malonic Acid Derivatives

13.17 : Loss of Carboxy Group as CO₂: Decarboxylation of Malonic Acid Derivatives

Just like β-keto acids—which upon thermal decarboxylation form ketones—β-dicarboxylic acids undergo decarboxylation to generate ...

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