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Chapter 13
Carboxylic Acids

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…
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…
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…
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…
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…
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…
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…
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.…
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,…
Reactions of Carboxylic Acids: Introduction
Carboxylic acids possess an acidic –COOH functional group. The acidity can be attributed to the resonance stabilization of their…
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…
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…
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…
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…
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…
Loss of Carboxy Group as CO<sub>2</sub>: Decarboxylation of &beta;-Ketoacids
Carboxylic acids, upon heating, undergo a decarboxylation reaction by releasing carbon dioxide gas. Monocarboxylic acids do not undergo…
Loss of Carboxy Group as CO<sub>2</sub>: Decarboxylation of Malonic Acid Derivatives
Just like β-keto acids—which upon thermal decarboxylation form ketones—β-dicarboxylic acids undergo decarboxylation to generate…
Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores
Molecular cruciforms are X-shaped systems in which two conjugation axes intersect at a central core. If one axis of these molecules is substituted…
Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with <em>p</em>-Nitrobenzoic Acid
Continuous flow technology has been identified as instrumental for its environmental and economic advantages leveraging superior mixing, heat…
Light-driven Enzymatic Decarboxylation

Light-driven Enzymatic Decarboxylation

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Oxidoreductases belong to the most-applied industrial enzymes. Nevertheless, they need external electrons whose supply is often costly and…

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