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Topic 10Carboxylic Acids

The carboxyl group, CO2H, combines a carbonyl and a hydroxyl group. In this topic we study carboxylic acids: their nomenclature, their physical properties and their acidity, the methods to prepare them and their reactivity, dominated by addition-elimination at the carbonyl carbon.

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The carbonyl group, C=O, is part of many organic functional groups.

In this chapter we study carboxylic acids, probably another of the most important chapters of the course.

Carbonyl-containing functions: aldehydes, ketones, carboxylic acids, esters, anhydrides, acyl halides and amides; the R groups modify the properties of the C=O group

Carboxylic acids

Examples of carboxylic acid nomenclature: 2-chloropropanoic acid, 3-butenoic acid, 2-(1-methylethyl)-3,4,5-trimethylhexanoic acid, 2,4-bis(1-methylethyl)-3-methyl-4-pentenoic acid, 2-(1-methylethyl)-3,5-dimethyl-4-oxohexanoic acid, 2-bromo-2-methylcyclohexanecarboxylic acid, 2-(2-formylcyclopentyl)acetic acid and trifluoroacetic acid (TFA)

Nomenclature

 Heptanoic acid dimer held by two hydrogen bonds, as a formula and as a space-filling model

Physical and Bond Properties

 0.1 M solutions of acetic, chloroacetic, dichloroacetic, trichloroacetic and trifluoroacetic acids with indicator: pH 2.91, 2.00, 1.39, 1.23 and 1.21

Acid-Base Properties

 Ants, producers of formic acid

Preparation

 Reactivity map of a carboxylic acid: strongly acidic OH hydrogen, electrophilic carbonyl carbon, basic oxygen centers and weakly acidic α-hydrogen

Reactivity